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Friends, I’ve been looking forward to writing about today’s company for a while.

There’s not one company I’ve ever seen…not one…that has so many incredible resources available for people like me to read up on and study. I had a call scheduled with the founder/CEO for this piece but ended up canceling because I could find everything I wanted to know through their documentation.

PostHog is truly an open book about everything. And that, to put it plainly, is the bedrock of their strategy: Open-Core everything.

They want you to know how and when they fail. They want you to know how their teams are set up. They want you to know how they get customers. They want you to know how they upsell their customers, and what their strategy is. They want you to know everything that goes on inside.

You might not have heard of PostHog before. If that’s the case, this is all you need to know: PostHog is the analytics platform for product engineers.

I know, we’ve covered a few analytics companies before. But we’re not talking about analytics products today. You know what these companies offer at the core level, and most of you are not building a directly relatable product. Everything we cover today can apply to you…the lens I’ve written through here is all about universal ways you could build and grow whatever you’re working on.

They’re just doing so much right that I had to give you a breakdown.

And if you want to see what PostHog does (product/web analytics, Session Replays, experiments, feature flags, surveys, CDP, etc), take a scroll of their site for a minute and come back. It’s worth doing even just to peak their unique legendary design/brand system and meet their hedgehog, Max.

Hedgehog!? Show me.

Expectations for today 🧠 🛠️

• Part 1: Along came a hedgehog (and their first 1000 users)

  • A story of 6 pivots

  • The first 1000 users

  • Playing for Product-Market Fit

• Part 2:

  • A laser-focused who

  • The open-core growth strategy

  • How this hedgehog does sales

  • Not boring

  • Selling microservices (and breaking up a monolith)

  • Nine ways this hog builds for speed

Reading time: 29 minutes 

I. Along came a hedgehog (and their first 1000 users)

PostHog’s path to product-market fit was defined by a series of rapid pivots.

Over nine months, founders James Hawkins and Tim Glaser built six distinct products, each addressing different challenges they encountered in their previous roles. They learned from each pivot too, going well beyond refining their ideas to sharpening their understanding of product-market alignment.

So without further ado, here’s how each iteration shaped their journey.

A tale of six pivots

#1: Sales territory management tool

The Idea: Inspired by James’ experience as a VP of Sales, their first product was a predictive analytics tool to help sales teams prioritize deals. By pulling pipeline data from CRM systems, the tool analyzed past deal data to predict the probability of success and flagged low-performing deals for removal.

What Happened: They secured interest from 15 sales leaders who agreed to test the product. But only one clicked the sign-up link. Still, the idea resonated conceptually, but it was overpowered for small teams and a poor fit for big ones who needed vast data sets to make it work.

Lesson Learned: → Confusion is costly. Targeting a large, mixed audience led to a disconnect between the product’s complexity and user needs. They learned that a good product needs a very well-defined customer profile. Without clear audience alignment, even a sound idea can fall flat.

#2: CRM with predictive analytics

The Idea: After seeing a friend replace their CRM with PostHog’s sales tool, they wondered if simplifying the CRM experience could be the solution. They built a CRM with predictive analytics, targeting small companies in need of a lightweight, intelligent CRM system.

What Happened: Getting meetings suddenly became a problem. The market was flooded with CRMs, and adding predictive analytics wasn’t how PostHog could sufficiently differentiate themselves. They secured one customer at $20 per month who ultimately didn’t even pay the invoice.

Lesson Learned: → Don’t enter crowded markets without a unique differentiator. By creating another lightweight CRM without a clear edge, they learned that relying solely on popular buzzwords or marginal features falls flat when creating product-market fit. Differentiation needs to be specific, clear, and rooted in a genuine user need.

#3. A 1:1 tool with predictive analytics

The Idea: Shifting their focus to help managers prioritize their team’s tasks, they built a 1:1 meeting tool inspired by Andrew Grove’s High Output Management. The twist? The tool included predictive analytics that highlighted deals worth discussing, adding context to performance meetings.

What Happened: They saw some early excitement, but only one out of 10 teams actually used it post-login. They hadn’t gone deep enough during discovery into whether users actively searched for a 1:1 tool, or if the problem of unstructured meetings was truly painful for them.

Lesson Learned: → Ask “why not?” before building. By failing to validate whether users actually needed or prioritized the tool, they built something that ultimately didn’t solve a pressing problem people would cough up for. This pivot reinforced the importance of asking whether a target user has actively gone out looking for solutions or workaround methods. Why? Because if not, there may not be real demand.

#4: Technical debt monitoring tool

Our idea was to help engineers manage technical debt. It didn't work out, but we realized the power of treating growth as an engineering problem. We also knew that many engineers struggle to understand the impact they have on the people who use what they build.

There are plenty of product analytics tools out there, but all the alternatives are SaaS-based. While they're powerful, they can be frustrating for developers. From our perspective, these tools can be problematic because:

• We don't want to send all our user data to third parties

• We want full underlying data access

• They don't give you choice and control over pricing

— James

The Idea: Aiming to tackle tech debt, a pain they knew from experience, they built a tool that prompted developers to log delays and frustrations after each pull request. This feedback then generated a “technical debt heatmap,” showing where in the codebase debt was slowing progress.

What Happened: This tool resonated the most. Enough to get them 600 users and a foot into Y Combinator. However, while teams found the tool helpful, the obstacle of tech debt remained. Product teams ultimately dictated priorities, limiting the tool’s influence and value.

Lesson Learned: → Focus on action, not just insights. People want more than insights alone. The best products empower users to take action or solve a problem. For tools targeting workflow or technical bottlenecks, it’s not enough to simply show users where their problems are—they need to show how to solve them.

#5: Engineering retention tool

The Idea: The 5th idea was a tool meant to spot disengaged developers early, allowing companies to address potential issues before they became critical. This idea came from conversations with advisors and targeted retaining engineering talent by monitoring team morale. 

What Happened: This was the shortest-lived pivot, getting canned in just five days. Engagement was low, and user response was indifferent. A conversation with a CTO who said he “didn’t have any big problems” underscored that their audience still didn’t see this as a high priority. Also, maybe a little Big Brother, no?

Lesson Learned: → Don’t chase ideas that lack founder conviction. Since this pivot didn’t originate from James and Tim’s firsthand experience or own insight, it was harder to articulate the problem and make it value for users. As you know, going after ideas that come from your team’s unique understanding is where the real winners come from. Speaking of real winners…

#6: Open-source product analytics platform

And on the 6th go, they found their home run play.

The Idea: Annoyed by relying on third-party tools to track their own product usage and the subsequent lack of developer control over data sent to these servers, they decided to build an open-source analytics platform for themselves…developers.

What Happened: This time, the pull was immediate. Within a month, they had hundreds of users, real community engagement, and positive feedback from the developer community. Unlike the previous 5 tries, they saw adoption and usage without extensive outreach.

Lesson Learned: → Listen to recurring frustrations to find product-market fit. This final pivot was rooted in a pain point they had felt firsthand and seen among other developers. By aligning deeply with a community need and solving it in an open-source way, they hit something with a very high ceiling of opportunity.

Learning from their pivots

1. Refine customer fit: Each pivot helped them refine their understanding of user fit, showing that not every “good idea” aligns with the right user profile.

2. Validate depth of pain points: They learned to find out whether their target market had any history of actively looking for a solution to a problem. This was how they learned to see if people genuinely wanted to solve something.

3. Actively leverage insights: Valuable products empower users to take action on insights, not just learn about problems. Insights without tangible next steps offtered can limit traction and retention.

4. Stay true to convictions: The most successful pivot was one they believed in most, and that addressed real, recurring challenges among developers.

The first 1000 users

PostHog’s first 1,000 users came from a mix of organic growth and community-driven engagement. Here’s how they made it happen:

1. Launched in public spaces: PostHog’s Hacker News launch didn’t jus thelp with visibility, but it got people talking. The first inkling of community. Posting on GitHub, where developers naturally congregate, allowed them to tap into a thriving ecosystem of developers already looking for new tools.

2. Focus on open-source: As an open-source project they appealed directly to the developer community. GitHub stars served as a key social proof metric, and the open-source format encouraged users to fork, modify, and contribute, creating organic growth that didn’t require any heavy marketing.

3. Transparent communication: By sharing their journey publicly and actively engaging with users, PostHog built trust. They frequently shared updates, responded to GitHub issues, and encouraged contributions. This all helped build on that growing community around the product.

4. Co-building with the community: PostHog treated its users as co-creators, making user feedback integral to the product roadmap. This two-way relationship allowed users to feel super invested in the product. And that’s how they turned users into advocates who happily spread the word.

Playing for Product-Market Fit

PostHog saw product-market fit as an always-moving target.

The team treated PMF as a cycle of building, releasing, and watching how folks users the product to figure out which features hit best with their audience.

Their journey to PMF included three core strategies:

1. Feature expansion based on real demand: Instead of overloading their MVP with features, they launched with a lean product and expanded based only by following clear user pull. Early feature additions like product analytics, feature flags, and session recording were all driven by many people asking for it, making sure they only added what clearly added to the product’s value.

2. Close monitoring of usage data: PostHog used its own product to track how people engaged with the features. By closely tracking adoption patterns, they were able to shape their roadmap in real time, focusing on high-impact features while deprioritizing (and unshipping) low-impact ones. 

3. Broadening reach to adjacent markets: PostHog’s product was designed to be versatile—supporting startups, scale-ups, and enterprise teams. This meant they could attract a broad range of users while retaining the flexibility to expand feature sets according to different segment needs. Meaning, that they could iterate their way to PMF across various user bases rather than getting locked in on a single corner of the market.

The big thing to remember here is that PMF isn’t a once-off goal you just get to—it’s an always-moving target. Product-market drift is absolutely a real thing.

II. How this hog has gone wild

A laser-focused who

PostHog has always gone for precision when defining their Ideal Customer Profile (ICP). This was largely about doubling down on a very specific audience with high standards and influence: product engineers at high-growth startups.

Defining the ICP

Their ICP isn’t just any engineer or PM—it’s the ambitious, skilled product engineer working on high-craft products at high-growth, engineering-led startups. These startups typically fall between Series B and IPO, with 15-500 employees and revenues over $100K per month, and are backed by top-tier investors. They’ve already hit product-market fit and are growing at a good clip, with teams that build fast, ship often, and depend heavily on data.

The power of this ICP is that it creates a great feedback loop: PostHog builds for high-performing engineers, attracting more of them over time, which, in turn, sharpens PostHog’s product focus and keeps it ahead of less technical analytics tools.

Why product engineers?

There are analytics tools that cater to the flip side of the market (non-technical generalists), but PostHog saw a future in engineering-led product teams.

This positioning reflects a strong belief the founders have—that engineering-led product development is the future of high-growth tech.

By building for technical power users, they’re aligning everything they do to meet the demands of engineering-driven cultures and the people who understand the data at a deep level.

Learning from High-Expectation Customers

PostHog’s positioning around these high-expectation engineer-first customers works for a few reasons:

1. Demanding standards: These users have high standards, which pushes PostHog to improve and create new products continuously.

2. Influence in the industry: The ICP that PostHog focuses on acts as a “key opinion leader” within the tech ecosystem. By winning over respected product engineers, PostHog earns credibility that trickles down to other potential customers, including technical founders and high-potential startups.

3. Word-of-mouth growth: Building for a specific user with an influential voice drives organic growth. Engineers have always been community-centric, and they regularly discuss and recommend tools to each other in engineering circles, which translates into referrals, broader adoption, and brand trust.

Avoiding feature creep

Like any good strategy, 80% of the substance is about what not to do. Related, a core part of their ICP strategy is knowing who not to build for.

They’ve deliberately chosen not to dilute their focus by catering to less technical users or non-core teams like marketing. Instead, they concentrate on making PostHog highly functional for technical folks. The rationale here is clear: by doing one thing exceptionally well, PostHog attracts users who would rather switch to PostHog for its tailored power than rely on feature-heavy tools built for generalists.

This focus on a single ICP comes with the discipline of saying no. PostHog resists adding features that would cater specifically to marketers (and expand their TAM), as this very likely would add unnecessary complexity and compromise the usability for product engineers.

Features are built for marketing teams only if they increase company-wide adoption, create cross-functional value, and enhance the core product experience for engineers.

The strategy beyond engineering teams

The company stage component of PostHog’s ICP doesn’t just stop at high-growth startups; it also includes high-potential startups and influential hobbyists.

The idea is that by serving the “next generation” of high-growth startups early, PostHog will become the default choice as these startups grow up. These high-potential companies—those backed by accelerators or led by former big-tech talent—use PostHog to inch toward product-market fit. PostHog’s goal is for these small, high-potential teams to adopt the tool as a foundational part of their product stack.

Hobbyists also play an important, if auxiliary, role in PostHog’s growth strategy. Engineers working on side projects or passion projects are often influential within tech communities, sharing tools they like with colleagues and online audiences. By providing a “free preview” of the product to engineers in this category, PostHog earns a steady flow of organic awareness and word-of-mouth promotion

The open-core growth strategy

PostHog’s open-core model isn’t just a feature of their product; it’s the foundation of their entire strategy. For an analytics company, this approach is unusual and ambitious, but it’s precisely this differentiation that makes PostHog so compelling to engineering-led product teams.

By creating an open-source product and leaning very heavily into a transparent company ethos (more so than any other company I think), PostHog positions itself as a highly customizable and trustworthy alternative in a market traditionally dominated by closed tools.

Here’s how PostHog’s open source strategy works as a growth engine, why it resonates so well with their Ideal Customer Profile (ICP), and how other companies can adopt key elements of this playbook.

Why open works

Product engineers often want control over their tools, which includes having access to source code, customizing it to fit their needs, and running it on their own infrastructure. By choosing open source, PostHog offers several distinct advantages:

1. Data privacy and control: Traditional analytics tools require companies to send data to third-party servers, which can create compliance and security concerns. PostHog allows users to self-host, giving companies complete control over their data—a huge advantage for privacy-conscious organizations.

2. Transparency and trust: PostHog’s open-source model allows users to see exactly how the tool works. For engineers who value understanding their tools deeply, this transparency builds trust and a sense of ownership. As a result, PostHog becomes not just a tool but a trusted part of the team’s infrastructure.

3. Customization for technical teams: Engineering-led product teams often need unique customizations that aren’t possible with SaaS analytics solutions. With open source access, PostHog’s users can extend and tweak the platform to fit their precise needs, creating a powerful advantage over tools designed for broader, less technical audiences.

Open Everything…the PostHog Handbook

An open-source platform is cool and all, but what stands out most to me is that they are open everything.

One of the most striking elements of PostHog’s open-source ethos is the comprehensive, public-facing PostHog Handbook. This document isn’t just a set of guidelines; it’s a living, breathing resource that captures every part of the company’s approach—from product decisions to operational strategies. Built after their first hire but before their second, the handbook became an internal compass and a powerful external signal of PostHog’s commitment to transparency.

Here are a few of my favorite documents they share openly:

• Compensation Calculator

• Share options

• Company strategy

• Business Model

• Roadmap

• Their side gig policy

The PostHog Handbook serves multiple purposes:

• Signaling maturity: When PostHog launched on Hacker News, the handbook helped them appear more established than they actually were. In a competitive market, this signal was crucial to gaining trust with developers who were hesitant to adopt an unproven tool.

• Attracting talent and users: By documenting their values and playbooks, PostHog has attracted talent that aligns with their building ethos. This approach helps bring them people who are truly excited about open source and committed to the mission.

• Living documentation: The handbook also acts as a centralized resource where team members and the community can suggest improvements. This collaborative approach ensures that PostHog’s processes and values evolve in real-time with input from those closest to the product.

Their public content strategy

PostHog’s open-source approach extends beyond the product into its content strategy. Rather than a conventional content playbook focused on SEO keywords, PostHog’s content marketing prioritizes honest sharing about what’s going on inside the hog nest.

By sharing their journey, decision-making processes, and product experiments openly, they create a best-in-class “build in public” narrative that appeals to its core users.

This build-in-public play doesn’t just build credibility though; it builds pipeline. According to co-founder James Hawkins, transparency was essential in the early days to gain traction as unknown founders in a crowded space.

Around 70% of their initial growth came from recommendations, with the other 30% driven by inbound content marketing. By continuously sharing valuable, transparent content, they built a feedback loop that has driven tons of growth.

My favorite layer of their open content is their newsletter:

Product for Engineers

Helping engineers and founders flex their product muscles

By PostHog

Here are the key components of their content strategy:

• Build-in-public: Sharing detailed updates, product decisions, and outcomes openly builds trust and interest.

• Always give actionable insights: By targeting their content to product thinkers, PostHog’s posts resonate with their ICP and drive inbound traffic from relevant audiences.

• Don’t sell: None of PostHog’s content tries to sell you on anything. They know content is about warming people up to the idea of one day buying. The goal is simple: add lots of free value, and keep people interested in our opinions.

• Engage the community: From their “community newspaper” to their newsletter Product for Engineers, PostHog uses content to keep their community engaged and involved in product development.

You, too, can be more open

For companies considering some level of an open-core strategy, PostHog lays out a few actionable steps we can take to use open source as a differentiator, regardless of your specific industry.

1. Find the right market fit for open source: Not every ICP values open source equally, so it’s important to ensure that open source is a benefit for your users.

2. Build trust with a public handbook: A public handbook has the potential to be a golden asset for you. It helps you outline your own thinking, it gives the team insights, and it’s a talent magnet. Companies can follow PostHog’s lead by documenting their principles, processes, and values, then sharing them openly. This not only helps you look more mature but also allows potential hires and customers to see if they align with your values.

3. Establish a build-in-public culture: Transparency doesn’t stop with a handbook. By sharing wins, failures, and lessons openly, you create a brand that feels accessible and trustworthy. PostHog’s content shows that technical audiences are hungry for real stories and actionable insights rather than polished corporate messaging. For companies starting out, consider sharing your journey.

4. Use open source as a product feature: If your ICP values customization, consider how you can make open source a core component of your product, giving your users the power to adapt and extend your tool to meet their needs.

How this hedgehog does sales

PostHog has built a developer-first approach to sales. One that’s built on transparency, speed, and user control. Unlike many SaaS companies that hide pricing and push multiple qualifying calls, PostHog leads with clear, usage-based pricing right on its website and a process geared for self-service.

If prospects need a demo, they skip the SDR gatekeeping and get a personalized call with a technical account executive who dives straight into the product, no fluff.

No hidden costs, just straightforward options

Hidden pricing or features bundled into opaque packages to maximize profit on each customer are all too common. PostHog cuts the curb here and offers utility-style, usage-based pricing that’s clear, flexible, and openly displayed. Customers see exactly what they’ll pay based on their usage, eliminating guesswork and building immediate trust.

It’s so worth checking out how they show their Pricing and Packaging. As you scroll, keep in mind how perfect this is for their ICP.

PostHog’s unique twist? Pick-your-own discounts. Customers who commit to longer contracts or higher usage levels can select a discount tier directly on the website—no back-and-forth haggling, no hidden negotiations. This approach removes friction and puts control back into the hands of the user, letting them make cost-saving choices without a sales pitch.

See their public “Choose your own discount” picker here.

From demo to deployment in days, not weeks

PostHog’s sales flow is designed for speed and minimal touchpoints. If prospects have questions beyond the website or pricing, they can book a demo directly with a technical account executive who can answer them. No layers of SDRs, no discovery calls for qualification—the focus is on value from the get-go.

PostHog aims to move users from demo to deployment in less than a week, offering shared Slack channels for prospects spending over $20K annually and setting up quick trials to get them hands-on immediately. Users get a direct line to experts and are encouraged to jump right into implementation—streamlining their path to value.

How to Apply This: Reduce your barriers between prospects and the product. Bypass qualifying calls and let technical prospects speak directly with product experts for faster onboarding.

Usage-based, modular pricing

Instead of bundling features into rigid packages, PostHog offers a modular approach that lets customers select only the products and usage they need. Customers are charged by individual products and usage, so they don’t overpay for features they don’t use. To further control costs, customers can set spending limits on certain features, like session recordings.

By allowing customers to start small and add products as they need them, PostHog creates a model that scales naturally with growth. This way, users don’t face large price hikes or restrictive tier upgrades as their usage grows—they can manage usage and costs on their own terms.

One contact from demo to deployment

Traditional SaaS models often hand customers off to various departments throughout the sales cycle, leading to a disjointed experience. PostHog assigns a single point of contact—a technical account executive—who works with the customer from demo to deployment. This continuity makes it easier for customers to get answers, understand the product deeply, and feel valued throughout the process.

To recap; here’s how they’ve made a dev-first sales model

1. Be transparent with pricing: Make all pricing information publicly accessible and straightforward.

2. Streamline sales for speed: Avoid multiple qualifying steps, letting prospects book directly with experts who can answer detailed questions.

3. Adopt modular, usage-based pricing: Charge for individual features or products based on usage to allow for more flexibility.

4. Assign consistent points of contact: Minimize hand-offs and ensure customers have a knowledgeable, single point of contact.

Not boring

PostHog stands out with a distinct, almost eccentric identity that’s instantly memorable. From the moment you see its quirky hedgehog mascot and vibrant, unapologetic design, it’s clear PostHog isn’t interested in playing it safe. They way they see it, brand is more than just a polished logo—it’s about amplifying their personality, reflecting their audience, and embracing the unconventional through honest weirdness.

As James Hawkins put it, “We’re going to have a weird, unusual style because we are the weird and unusual one that’s joined [the analytics market], and that’s how we'll win.”

A mascot that matches the mission

PostHog’s brand story is rooted in creativity and some eccentricity. The inspiration for their unique brand voice came from a chance Twitter encounter, where designer Lottie Coxon caught their eye with her unconventional portfolio. This led to the iconic hedgehog mascot—Max, a quirky figure that’s as memorable as he is unusual—and a visual identity that fits PostHog’s open-source, community-driven ethos.

It’s a brand where weirdness isn’t just tolerated; it’s celebrated and built into the DNA.

Early iterations of PostHog’s branding were more experimental than polished. Lottie describes how the initial brand look took shape: “The hedgehog mascot was somewhat of a happy accident. We wanted something that genuinely reflected who we are, and hedgehogs somehow just felt right.”

This happy accident was emblematic of PostHog’s core philosophy: sometimes, leaning into quirks reveals a brand’s true character better than any polished branding exercise ever could.

Consistent and memorable

Unlike most brands that tone down the oddities to appeal to a broad audience, PostHog leaned in. And they do it in big and small ways. Beyond the mascot, their website, product, and communication style have an irreverence that feels more like a zine or a fan club than a B2B software brand. Even their product copy avoids the safe, over-polished tone of typical SaaS. It’s unfiltered, often humorous, and directed squarely at engineers.

This is a company that isn’t afraid to be a little “too much” because it’s exactly what endears them to their user base.

One example of this is their FAQ section, which includes playful quips and refreshingly blunt responses like “Yes, we do hate bureaucracy too,” or “You’ll hate PostHog if you like lots of sales calls and qualifying sessions.” This voice is consistent across every touchpoint.

It’s obvious they’re not interested in being everything to everyone (remember—who they are not for)—they’re proudly the choice for the rebelliousness engineers. If it repels some, so be it. That’s design, and it’s PostHog’s way of keeping its community aligned with its culture.

Kill marketing-speak

“Marketing-speak” is the worse. More and more, it’s got a growing negative connotation.

Most companies avoid the quirky and opt for bland, broadly accessible branding out of fear it could alienate potential customers. PostHog’s knows, and has proven, this isn’t the right strategy today.

Being weird isn’t just a style; it’s a differentiator that helps them stand out. PostHog’s approach has built a tribe-like following, where customers feel aligned not only with the product but with the spirit of the company.

PostHog’s weirdness goes beyond its public image. Internally, the company embraces fun as a core value, from team Slack emojis to custom merch items (they started with a T-shirt, and now they’re experimenting with everything from shower curtains to collectibles).

When founder James talks about the role of fun, he refers to an insight from his executive coach: the most successful billion-dollar founders aren’t just in it for growth—they genuinely love what they do. That spirit permeates PostHog, creating a team that’s as excited about their brand as their customers are.

Selling microservices (and breaking up a monolith)

We’ve somewhat touched on this with the pricing stuff, but there’s more to explore here.

Most SaaS companies bundle all their features into one platform, then sell that platform in one subscription. Let’s call this monolithic selling.

PostHog has taken another route, approaching each feature as its own standalone product. With each tool sporting an independent roadmap, team page, changelog, and even separate pricing, PostHog essentially functions as a suite of “micro SaaS” products housed under a broader data and analytics operating system. This is their “microservices” approach—a term more commonly seen in architecture but brilliantly applied here to software.

Here’s why it works, and how other startups might consider adopting similar principles.

Why not just bundle?

Most companies offer their features under a single product umbrella. It's simple and can be easier to sell. But simplicity in packaging doesn’t always translate to a better user experience. PostHog recognized that by allowing each feature to operate as its own product, users gain more flexibility, personalization, and freedom to pick what they need—whether it’s session replays, heatmaps, or advanced analytics.

Take Lempire another company known for selling microservices. By creating independent tools for each function (e.g., for email outreach, personalization, and lead management), they offer users a very modular experience that lets them pay only for what they need. Each product gets treated as it’s own startup with growth and commercialization metrics, and it becomes easy to establish a playbook for expansion—just launch another startup and give it the resources from the parent brand.

PostHog’s model is similar, allowing technical users to piece together an analytics stack rather than forcing them into a one-size-fits-all tool.

I absolutely love this approach, and if I ever build a software company again I’d want to build it this way. There’s just something very neat about having each product you build be its own siloed thing.

Why microservices work so well for PostHog

This approach plays to PostHog’s strengths and user needs:

1. Flexibility for power users: By making each feature a separate product, PostHog caters to technical users who appreciate control. Each tool can be turned on, off, scaled up, or scaled down as needed, giving users a developer-friendly modular experience.

2. More control and value for each product: PostHog can refine and improve each product independently, focusing on specific use cases and iterating faster. This allows the engineering team to prioritize enhancements within individual tools, leading to an overall platform that feels far more tailored and high-quality.

3. Differentiated pricing for developers: Each tool has its own pricing structure, which means users aren’t locked into an all-in-one model. They only pay for what they use, which fits the developer mindset of “don’t waste resources.” This approach lowers the barrier for users to start with PostHog and then expand as needed.

4. Maximizing market reach: The microservices structure gives PostHog the ability to enter new markets by creating entirely new products without impacting their existing ones. This approach has allowed them to rapidly expand their toolset, testing, and iterating on new products as they go. With each new product, PostHog increases its addressable market while keeping costs under control.

Building wide, operating small

This strategy is supported by PostHog’s organizational structure. Instead of one large engineering team, PostHog splits its workforce into smaller, startup-like units, each responsible for a specific product. These “mini-startups” are given autonomy, with teams free to make decisions and ship improvements without layers of management approval. It’s a refreshing model that prioritizes speed and autonomy and keeps PostHog nimble even as they expand their product suite.

…

For early-stage companies, the microservices model may not make sense immediately, but it’s definitely something to think about as a growth strategy once you’ve validated product-market fit for your first product. '

Here’s how you could start implementing a similar model

1. Design each new feature as a potential product: Treat each new feature like its own micro product, with a clear ICP, positioning statement, clear user outcomes, a roadmap, and metrics to gauge impact. This helps teams assess if the feature has the potential to stand alone, and if it resonates with users who might just want that one function.

2. Hire for product ownership: Look for hires who thrive with end-to-end responsibility. By hiring product leads who operate with a startup mentality, you create a culture of ownership, accountability, and entrepreneurship.

3. Think of your homepage as a storefront. If you’re selling microservice products, think of your main brand as the front-of-shop store where people can buy your products. Scroll through this site to see a good example.

The microservice model isn’t for every startup, but it’s a smart choice for those looking to serve a diverse range of users and scale product complexity without adding operational drag.

10 ways this hog builds for speed

This is more along the lines of how PostHog builds product, but that does directly tie into how they grow, because speed often = growth.

So I’ll, quickly, share a few things they do to ship fast.

1. No design by default: PostHog’s engineers don’t wait on designers to get started. Engineers design the UX, especially given a well-established design system. While a designer is available, they work reactively to support ongoing work without holding up the release.

2. Minimal product management: Product engineers take full ownership of user feedback, roadmap decisions, and metrics like revenue and costs. They’re empowered as “product engineers” rather than relying on traditional product management. There’s one PM who steps in only if a team needs extra support.

3. Hiring for autonomy: Every hire is screened not only for skill but for how well they work independently. Most are highly experienced and can self-manage, a key asset for PostHog’s all-remote, autonomous culture. New hires even work on a real project during hiring to gauge their independence/resourcefulness.

4. Small, startup-like teams: PostHog organizes teams around each product as mini-startups. Each team of up to six people has complete control over product decisions, including marketing and pricing, allowing them to ship quickly without waiting on cross-company approvals.

5. Engineering-led org: PostHog keeps overhead minimal, with most roles tied to engineering. Outbound sales are off the table, and the company’s marketing team is lean. The focus remains product-led, keeping development in line with user-driven product demand.

6. No meeting Tuesdays and Thursdays: To give engineers as much time as possible for deep work, PostHog avoids meetings twice a week. This focus on fewer, shorter meetings helps maintain productivity, with asynchronous updates and only essential synchronous catch-ups.

7. A late mover’s advantage: PostHog only builds products in markets with proven demand, where there are $1B+ competitors. This ensures demand while giving PostHog the opportunity to integrate tools in ways competitors can’t.

8. Strategic venture capital: With thoughtfully raised venture capital ($3M seed, $9M Series A, and $15M Series B), PostHog maintains a well-paced runway for building new products without excessive spending.

9. Trust and feedback over process: PostHog minimizes rigid processes, preferring to trust its teams and provide direct feedback when needed. The aim is for maximum autonomy, with a strong focus on trust rather than bureaucracy

10. Documenting everything: Writing things down saves time, eliminates scheduling headaches, and keeps the team aligned. Information becomes accessible to everyone, from onboarding to product strategy, and it helps to avoid endless meetings and gives everyone a clear sense of direction

Go down the rabbit hole

• Non-obvious behaviors that will kill your startup

• How PostHog operates

• The companies that shaped PostHog

• Navigating Growth and Retention: Lessons from PostHog’s CEO

• The habits of effective remote teams

And that’s a wrap on our PostHog deep dive! I hope you learned something new and are walking away with some inspiration to bring to your own product.

I’ll see you next time.

—Jaryd

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Friends, it’s good to be back with the deep dives. I know it’s been a minute.

We’re returning with a breakdown of June: The new kid on the analytics block that is growing with such a neat strategy.

We all know the saying…Keep It Simple, Stupid!

I’ve known KISS for ages—we all have—but it’s one of those things we know yet easily and often forget.

I’ve been passively thinking about startup ideas, and one of my main criteria for an idea is a solution that can lean LESS, while everyone else has indexed on MORE.

Something that cuts the frills and just excels at solving some fundamental need in a basic way.

We’ve covered many times in this newsletter how platforms (MORE) always win. But my definition of winning has been changing, and I’m warming up to the idea that simple and elegant tools (LESS) that are cash-flowing and profitable (perhaps with smaller valuations) are a fantastic way to win.

Of course, you can still be incredibly valuable with simplicity. The ceiling, as it is in June’s case, is very high by indexing on LESS.

There’s a lot June is doing right to wedge in and grow in a crowded market, and we’ll cover all the actionable stuff, but the big play that differentiates them from pretty much every other analytics company out there is that they’ve built for simplicity. And to be more specific…simplicity for generalists.

It’s such a sharp strategy, especially when you zoom out and realize they’ve stacked a series of micro tactics together to shape one cohesive play.

Expectations and snackable insights 🧠 🛠️

I’ve packaged 20 hours of research/analysis into a 32-minute read. Here’s the gist if you’re short on time:

• Founder-led marketing is the future of brand building. June’s founder/CEO, Enzo Avigo, turned his personal brand into a narrative-first marketing engine—an engine driving millions of monthly impressions on LinkedIn. In short, faces (employees) beat logos (the company) because we trust people over brands.

  • Key insight: As icky as you might think it is, go and invest in building your personal brand. When you have a product to market, it will be your lever for authentic and value-driven content.

• Radical simplicity (generally) beats radical flexibility. Most of the analytics tools you can think of are geared toward specialists with complex and customizable features. But June zags while others zig, and they obsessed over simplicity through an opinionated product that makes data accessible to generalists. This strategy has allowed them to capture a large and underserved segment within an entrenched/mature market.

  • Key insight: You can grow not in spite of, but because of stripping your product down to focus on the core, and constant, needs of your market.

• Strategy doesn't have to be one big thing—you can stack a series of micro strategies. June combined three key chess moves—simplicity, company-level insights, and targeting generalists—to build a unique and defensible position in the analytics category. I like to call it a holistic strategy of opposites.

  • Key insight: Stacking complementary strategies can amplify your product’s impact and unlock a compounding advantage that’s more than the sum of its parts.

• Focus on Minimum Remarkable Products (MRP), not MVPs. June challenged the outdated idea of shipping bare-bones, buggy MVPs. Instead, they focus on shipping polished, remarkable products that delight users from day one.

  • Key insight: The bar for "viable" is higher than ever. People have no time for subpar experiences. And by making something aesthetically remarkable from the get-go is how you can catch and keep people’s attention…setting you up to create long-term relationships

Let’s get cracking!

Part 1. Starting June

Why so serious?

Analytics, as boring as it might sound, has been behind decisions since the days of the ancient Egyptians. They used early forms of measurement and tally systems to track goods and resources for trade. And build the pyramids?

Fast forward to the 1800s, and analytics makes a big progressive leap with the introduction of the Tabulating Machine and the punch card—that little piece of paper with holes in it developed by Herman Hollerith to process data for the US Census.

This step change in analytics laid the first piece of groundwork for the rise of computers, which of course led to modern digital analytics.

Now, as users of software, we can’t escape having every interaction we take tracked, and as builders of it, we can’t escape the constant fire hose of data coming at us. So much of it we don’t even know what to do with most of it.

That’s just a basic problem that many teams face: Tons of data; very few people able to use it effectively.

I literally see this all the time at my company. We have the best tools and so much analytics in place, but overall we tap into just the tip of what’s possible, meaning we pay for a lot more than we use.

I’ll be the first to tell you that I love Amplitude. I use it all the time, it’s a fantastic product, and I’ve praised them widely. But it’s advanced, and only a handful of folks at the company are able to use it well enough. Amplitude, like many of the other analytics companies, are geared at data-ish specialists within an organization.

It’s ironic because you’d think with such sophisticated software more people would be diving into the data. But most teams are still sitting on a mountain of info they never fully leverage. In fact less than 10% of employees in most companies actively use analytics.

And even though the number of data points is exploding (for better or for worse…maybe worse…), we’re still relying on the same small set of specialists to interpret it all.

It was this insight, spotted as a direct point of frustration while working at Intercom, that compelled Enzo Avigo and Ferruccio Balestreri to build something that flipped the script…something that could empower everyone on a team to be data-centric…something refreshingly simple and fun.

Extrapolating out an insight

So, in a very crowded space filled with more features, more graphs, and more complexity, June said, “Let’s build for the other 90%.”

But as Enzo experienced this first hand and observed it across Intercom, he didn’t rush off to immediately build something. Instead, he focused on honing his insight to see if more people experienced the same problem, as well as to try to connect what he was noticing to broader market inflections.

There’s a great lesson in that: Spotting an opportunity requires you to not only understand the problem but to attach it to a broader shift—the best insights come when you can align a personal frustration with an external inflection, allowing you to see where the market is heading before others do.

Here’s how you can do as Enzo did…

1. Hunt for 1st or 2nd degree frustrations. We all know the advice of following your own problems, but if you’re working for a company, another source of startup ideas could be actively hunting for inefficiencies that your colleagues/team might experience. You know your team isn’t a 10/10. So whatever the delta is between your ranking and a perfect score, what’s a problem people are ignoring because it’s simply a mission to solve? Once you find it, ask yourself, “Is this unique to us, or could it be more common?”.

2. Study the ecosystem: Before you can have an opinion on how to win in the market, you first need to know where to play. And that’s not just picking a market that looks promising; it’s about deeply understanding the landscape, the players, segments, the segments within segments, and what the opportunities potentially sitting right beneath the surface are. The only way to do that is to immerse yourself in the ecosystem and ramp up on knowledge. People often say founders who build in a domain that they are familiar with is crucial, but the opposite can be equally true. Being unfamiliar means you’re not jaded to schleps and inefficiencies, and if you learn the state of things correctly, could well be in a better position to spot opportunities. All you need is a framework for learning fast and smart.

3. Map out the market inflections: We’ve spoken several times about the shifts that create a new wave of opportunities. For June, one of the biggest inflections was the rise of product-led growth and the increasing importance of being data-informed. Yet, the tools to support this shift were still tailored to specialists, not the broader teams who needed access to insights. One tactical thing you can do here is to…

   • Look for contradictions: What’s something that everyone believes, but might be wrong? The idea that analytics had to be complex and tailored to specialists was a core assumption that June challenged. Finding these contradictions in your market can often lead to the biggest opportunities.

Gaps in the market…markets in the gap

Just because you find a gap in the market does not mean there’s a market in that gap. Or less poetically said: solving a problem doesn’t mean people are willing to pay you for it.

So, with a seemingly strong insight and a sound vision/mission to follow through with, June’s next step was to increase their fidelity on what the product to get there would look like—a product that resonated with the market and that people would pay for.

They started with a series of smaller, lower fidelity, bets—testing their assumptions with quick low-effort-high-learning prototypes. Each experiment wasn’t a pure linear progression of the product, rather they approached the problem through a different lens. Each time, giving them a sharper focus on what the right framing was.

Here’s a breakdown of what they did. A simplification, of course…

• The first prototype: Their initial product was a no-code layer on Google Tag Manager. It allowed teams to track events without needing a developer. While it was a step in the right direction, the feedback was clear—it solved a small part of the problem but didn’t offer the simplicity they were aiming for.

• The second prototype: Next, they built a plugin for Figma that allowed users to annotate design files with tracking events. Another experiment focused on improving collaboration between design and product teams. It solved the problem through a different lens, but it still didn’t resonate with their core audience.

• The third prototype: The inflection for them came when they built a Google Analytics-style tool, specifically designed for startups. This version simplified the data, offering clear insights without overwhelming users with unnecessary complexity. It resonated deeply with their audience.

While the initial observation and insight remained consistent (the gap in the market), it was only through these iterations that they learned what people really needed (the market in the gap)—an analytics tool that provided value right out of the box, without complex setups or overwhelming dashboards.

Part 2. How June Grows

The other day on YouTube I came across this excellent Mint Mobile ad. In 30 seconds, Ryan tells us that Mint does the opposite of Big Wireless.

It’s such a crisp narrative that paints a clear picture of how Mint differentiates itself. Give it a watch below.

Ryan says…

• “They charge you a lot” → “We charge you a little”

• “They put their names on arenas” → “We put ours on my lower back”

• “They’re raising their prices due to inflation” → “We’re deflating ours due to not hating you.”

There are only a few words to shove in an ad, but I was thinking afterward, What else does Mint do differently from the other carriers? E.g:

• They have physical stores → Mint is digital only

• They have longer post-paid plans → Mint offers short-term prepaid plans

What I noticed was that Mint was threading together lots of little inversions to create a more substantial: “Our differentiator is doing the opposite of what the market has come to expect.”

June has done the same thing.

It’s a strategy that isn’t just a single move—rather, it’s how they’ve stacked these opposites together to create a larger, cohesive offering that stands out in a market that’s easy to get lost in the crowd.

Let’s cover three of their main “opposites”, plus 5 other takeaways from their growth story.

June has been an ongoing sponsor of our 5-Bit Friday’s for a while. So I’m giving them another punt here (because clearly I think they’re doing something very right). As a HTG reader, you can get 25% off June.

Try June

1. Simplicity, opinionated software, and growing with less

🫰 Why it matters: There’s too much complexity in the world. I think for a long time, the tech ecosystem has indexed on more flexibilty. But, having an opinion as a team and turning that into opinionated software for your audience is a great way to make a happy customer. Just think about how you (probably) like it when a waiter gives you a recommendation at a restaurant and the menu is a single-side print, saving you from an overchoice spiral.

🥇 Applying it: Unship features, rethinking your UX/UI, and regularly ask the question: How can we help customers get what they want with fewer steps and clicks? Simplicity isn’t about doing less; it’s about doing what matters most better.

Let’s go deeper…

Most analytics tools are built for people who are comfortable working with data. They’re dense on features, can be customized in so many ways, and have complicated and timely implementation phases to even get to the point of seeing value.

This has made using data for the majority of users who just want actionable insights more difficult.

This is where June zigged while the rest of the market has been zagging.

Simplicity, to state it simply (🤘), means being easy to understand, use, clear, specific, and actionable. It’s where the confusion is low and intuition is high.

And simplicity sells. Here are some numbers for you to prove it:

• Simplicity drives love: 64% of consumers are more likely to recommend a brand because of simple experience.

• Simplicity drives growth: Since 2009, a stock portfolio made up of the simplest publicly traded brands (as defined by Siegel+Gale) has outperformed the market by 686%.

• Simplicity drives sales: 55% of consumers are willing to pay more for uncomplicated experiences.

It’s not just because it always works, but more fundamentally, we crave it. Our brains always opt to use the least amount of energy to understand something. So when we’re fed jargon, confusion, or complexity we resist them.

Like it or not, we’re apes that look for simple alternatives.

One of the most prolific examples of success through simplicity is Apple.

Jony Ive, Apple’s Design Guru, spoke about how Jobs pushed relentlessly the iPod to be free of clutter and complexity.

Apple has continued this core tenet and makes its UX engaging by eliminating features. Features are always added with thought and consideration in updates, only once the user is ready to receive more. It’s a strategy that allows users to get comfortable with the current experience and then train them to be fluent in using the product.

I truly believe simplicity should be the metric that drives brand, design, product, and business objectives. It is probably one of the most reliable levers to pull to bring about consumer happiness and loyalty. IMO, simplicity deserves a place in strategies.

In June’s case, by eliminating the unnecessary and building for intuitiveness and structured opinions across the product, they’ve crafted a product that offers equivalent or even more value by zeroing in on the fundamentals.

It’s been the basis of their GTM. And just looking at other onboarding experiences, you can see how they’ve nailed it:

• Setup in 30 minutes. June asked the question, “How do we save companies hours of typical instrumentation?”. And the answer was to give companies a single snippet to add to their website. It takes just a few minutes. That’s all they have to do.

• Automatic dashboard: June asked the question, “How do we show companies valuable information ASAP?”. The answer was to take the onus of chart building off the user and give them instant dashboards and reports, showing them insights without them having to navigate any product learning curve.

In short, June saw an underserved segment of users who were frustrated/limited by the unnecessary bloat and leaned into it to create their first opposite position.

A quick look at emerging disruption strategies

I’ve touched on the broader playbook here already—disrupt by doing the opposite of what incumbents are doing.

It’s about spotting the things that the major players are either unwilling or unable to fix and then countering by offering a product that specifically addresses those pain points for either a smaller niche or a larger majority.

I wanted to call this out again because as I was writing the above, a few other examples of emerging ways startups are differentiating via opposites came to mind.

• Chrome → Arc: Chrome dominates the browser market with mass appeal, but Arc disrupts by counter-positioning itself with bespoke design norms and craftsmanship. Arc isn’t for everyone—it’s for innovators and tech-savvy users who crave something radically different.

• Gmail → Superhuman: While Gmail serves the masses, Superhuman disrupted by going premium, offering a luxurious, high-speed email experience for CEOs and busy executives who can’t stand the inefficiencies of traditional inboxes.

• Pendo → CommandAI: Where Pendo does onboarding by pushing information to users, CommandAI inverts the use case norm by pulling users to information when they need it, becoming the ideal product for teams who hate disruptive pop-ups.

• Amplitude/Mixpanel/Heap → PostHog: PostHog is another incredible analytics company that I’ve been learning about, and their differentiator from both the incumbents and June is they are open source. A similar play to Meta and beehiiv countering Apple and Substack’s closed ecosystems.

In June’s case, the first opposite is simplicity. Let’s move on to the second.

🔑 Bottom line: Customers appreciate, and really do pay you at the end of the day, for you opinions. That often means keeping what you sell them simple and making the right recommendations for them. Just minimize any thinking or their part.

2. Inverting the use case norm

🫰 Why it matters: Pretty much every analytics tool you use focuses on behavioral data at the individual level. AKA, the expected use case is understanding users. June (surprise) has done the opposite. They’ve prioritizing company-level insights. And for B2B SaaS companies, understanding how a company behaves—rather than just individual users—is often far more actionable.

🥇 Applying it: Consider what the standard workflow in the market is. How does, at the fundemental level, the core JTDB get solved? Then consider whether this is because it’s the perfect way, or whether inertia has just kept the status quo in check and nobody’s thought to invert it. Often by taking the usual approach and flipping it, you can address underserved needs and unlock value where others aren’t looking.

Let’s go deeper…

In the golden age of B2C, companies like Google Analytics, Amplitude, and Mixpanel created a culture where understanding individual users—what they clicked, how they navigated, and where they churned—was the holy grail of insights.

But as the shift toward B2B SaaS accelerated, this model showed some cracks…and Enzo saw them

As you know, selling to businesses vs consumers is a different beast. When Notion the company is your customer ($100K+/year), vs Joe who works at Notion ($100/year), you need to understand the whole picture through a different lens.

Rather than looking at isolated user actions, you need to understand how entire companies, or accounts, are engaging with your product. The dynamics are different when you have multiple stakeholders, decision-makers, and users all interacting with your software in different ways.

But you need to know how the company as a whole interacts with your platform because, without that clarity, it’s more difficult to drive expansion, reduce churn, and increase the customer’s overall success with their team using your product.

But that lens is tricky to get right when the paradigm is individual-level data first.

Round peg; Square hole.

This is where June saw an opportunity to invert the analytics use case. For instance, their platform automatically creates profiles and reports on each company customer. These reports give rapid instant insights into activation, retention, and expansion at the account level, making it easy for teams to understand which accounts are doing well, which need attention, and who’s ready for an upsell.

Also, instead of overwhelming people with endless graphs and dashboards, June just cuts to the chase with a one-click feature analysis that provides a curated set of graphs telling the story of how an account is engaging with the product.

How to steal this tactic

Even more so than simplicity, inverting the use case norm is likely June’s biggest micro tactic within their larger Strategy Of Opposites.

Being simpler is great, but competitors can copy that more easily than changing the foundation of how they solve the problem.

Of course, it’s not impossible for others to, say, layer in a B2B portal like this to compete with June, but then they’re just making their already complex products more complex. Meaning, people will likely prefer June’s simplicity even more.

This is an oversimplification, but you can see how the one tactic supports the other to create deeper levels of defensibility.

This kind of inversion strategy can be incredibly effective in any market. Here’s how you can try it, even as a fun thought experiment.

1. Identify the dominant use case: Start by understanding the norm in your market. What are the incumbents focusing on? What is their product designed to solve?

2. Find the gaps. Reframe the problem. Look for underserved or frustrated segments of users within that market. You might find that the dominant use case in your market leaves out an important segment of users whose needs aren’t being met. Think about how the problem could be solved differently by taking the opposite approach.

3. Flip the script: Take the dominant use case and invert it. For example:

   • If incumbents are focused on single users, focus on accounts or teams.

   • If they’re focused on one-off transactions, build for ongoing relationships.

   • If they’re delivering complex, multi-step processes, streamline them into something that can be done in fewer clicks.

4. Build for the next wave: June didn’t just invert the norm for the sake of it—they did it because they saw the next wave of growth in B2B SaaS. Identify where your market is headed, and build your product around where things are going, not where it is today.

🔑 Bottom line: Inverting the use case norm is often a way to reach underserved, on the fence, customers.

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3. Go narrower or go wider…and commit

🫰 Why it matters: When picking your target customer, you can can either niche down and specialize, or widen your aperture and build for a generalist. Whichever you pick for your GTM, the key is making that decision with conviction and aligning your product with it. Playing both sides is tough.

🥇 Applying it: After identifying a gap, you need to understand the scale of the market within that gap. The audience you choose defines your product’s complexity, messaging, design and brand, and growth strategy.

Let’s go deeper…

June’s decision to target generalists with soft data skills instead of specialists with hard data skills was very strategic.

Generalists have a different Job to Be Done. They’re often wearing multiple hats and don’t have the time to spend hours configuring dashboards or interpreting complex metrics. They need quick, actionable insights that are relevant to their role. They can’t be blocked by data when making a decision.

Most analytics tools (think Amplitude or Mixpanel), are designed for more technical PMs with solid data skills or entire data teams. Tools like Looker and BI platforms are aimed at professionals who have some technical savvy to navigate their complex interfaces.

Google Analytics is user-friendly-ish, but it’s more of a jack-of-all-trades across B2C and B2B that isn’t great for teams beyond marketing.

By widening their aperture, June expanded their TAM significantly. But more importantly, they catered to an audience that had been largely ignored.

Advice on when to Zoom In or Zoom Out on your target market

So, when do you follow the classic advice of defining an even more specific customer, vs being a more generally appealing product?

1. What’s the complexity of the problem you’re solving? If the problem is complex and unique to a particular vertical, it often makes sense to start narrow. If your product can be easily understood and used by a variety of roles without customization, a broader market might be the way to go.

2. What’s the current landscape? If a market is saturated with niche tools, there’s often room to zoom out and target a generalist audience that’s overlooked. The reverse also applies. This is similar to the concept of “innovating” by bundling (generalist) vs unbundling (specialist).

3. What’s the breadth of your product’s use cases? When testing your product in the market, pay attention to who gravitates toward it. If you’re naturally seeing traction with different types of users across various industries, you might have a generalist product on your hands. However, if adoption is strongest among a specific segment, lean into that and double down on the niche.

4. Think about scalability and product requirements. Going broad means your product will need to be versatile and simple enough to meet various needs without extensive customization. On the flip side, a focused approach allows for deeper, more specialized features, which are usually less scalable to a general audience.

5. Does your market scope match your resources?
   Appealing to a broad audience can mean more resources for support, product iteration, and marketing. For earlier-stage teams, starting with a tighter focus can lead to tighter learning and the building of stronger relationships with a specific type of customer. Often, that’s a more sustainable path to early traction.

The power of stacking strategies

To put a bow on these three sections before moving on, we can see June combined three micro strategies to create a larger, cohesive GTM advantage.

Any one of these strategies could have been effective on its own, but by combining them, June created something much more defensible and unique. T

• Move 1: Simplicity, not bells and whistles and deep customizations.

• Move 2: Company accounts, not Users

• Move 3: Generalists, not Specialists.

I like to think about this as a “strategy of opposites” which has given June a distinct edge. By stacking all three together, they made it difficult for competitors to replicate their approach and have created their own micro category within product analytics.

Another example that comes to mind is Slack. Their early micro strategies were:

1. Team communication: Slack didn’t invent workplace messaging, but they refined it with seamless, team-based communication that replaced email threads with channels.

2. Any team: Originally marketed as a team messaging tool for developers, Slack quickly shifted to focus on a more generalist audience: all teams needing better communication, from marketing and sales to HR and design.

3. Developer ecosystem and integrations: They created an open API that allowed third-party integrations, letting teams connect their workflows from different tools directly into Slack (e.g., Google Drive, Zoom, Jira).

4. Consumer-grade UX for enterprise: Slack prioritized a simple, user-friendly design that felt more like a consumer app than an enterprise tool, making it easy for teams to adopt.

Their Stacked Strategy: Together, these created a highly sticky product that not only solved communication problems but also became a hub for generalist team collaboration.

In short, whether or not you’re playing a game of opposites like June, Strategy Stacking can be a really helpful mental model.

One piece of advice here is this: Not all strategies stack well together.

You need to test for compatibility. How do tactic A and tactic C interact? Do they reinforce each other, or do they create friction? The goal, of course, is for your product strategy to feel cohesive and intentional

🔑 Bottom line: Commit to your audience, whether niche or broad, and align every part of your product and strategy around that choice. If you’re stacking strategies, ensure they’re compatible and reinforce each other to create a cohesive and defensible market position.

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4. Obsesses with minimum delightfulness

🫰 Why it matters: While all analytics tools feel serious and “professional”, June has leaned into a playful and approachable design. Their focus on delighting users—through colors, fonts, and an overall fun factor—creates an emotional connection that competitors often overlook. This isn’t just about aesthetics; it’s about ensuring that every interaction feels easy, light, and enjoyable.

🥇 Applying it: Easy, delight users. Delight users. Ask yourself before signing off on designs…How could we delight users more? It's not enough to have a functional product anymore; people want products that make them feel good while using them. This means investing in design, user experience, and overall narrative, even (nay, especially!) from early versions of the product.

Let’s go deeper…

From their vibrant colors to their friendly font choices, June has created an aligned brand tone and product experience that is very approachable—a quality that might seem minor but makes a huge difference in user adoption.

Another deliberate tactic that reinforces their larger stack of opposites (Serious/Dry → Playful/Lively).

This approach echoes an important concept from one of Enzo’s reflections as a founder…great brands are built on unrecognized truths.

One such truth is that analytics tools don’t need to feel heavy or overwhelming to be powerful. By focusing on making the product approachable and delightful, June is redefining what users expect from an analytics platform.

The commitment to being at least minimum delightfulness, as Enzo told me, reflects in every release. What goes out must a) Add value and b) Add joy.

That’s a philosophy that for sure sets them apart, and is something that has personally inspired me to push for more joy in my releases. As product leaders, don’t discount holding a higher bar for delighters.

You’ll build more emotional connections with your users.

Evolving from MVP to Minimum Remarkable Product

June’s product philosophy also challenges the outdated idea of shipping a Minimum Viable Product (MVP).

The advice you’ve had drummed on you for decades has been if you’re not embarrassed by your first product, you’ve shipped too late

And that advice has created a huge amount of enterprise value. I’m not knocking it. But I am saying (in agreement with over here) that advice gets dated.

Scrappy first versions of a product worked great when the comparative solution was pen-and-paper, Excel, or phoning and waiting for ages to get a taxi.

No matter what you launch today, the alternative (at least in the consumer’s mind) isn’t something outdated, it’s a modern software product.

As Kyle says: “It’s increasingly easy to build software and increasingly hard to distribute it. It’s especially hard to distribute a product that isn’t ready for primetime. Once you lose someone’s trust, it’s nearly impossible to win them back – let alone ask them to share your product with a friend.”

This creates a new norm: The Minimum Remarkable Product (MRP).

As we saw already with June’s early days, this shift doesn’t mean it’s not important to move quickly and test hypotheses, it just means quality is now non-negotiable.

If your product lacks polish, doesn’t feel dependable, or fails to delight, users are unlikely to return or recommend it to others.

How to elevate product quality without slowing down

It’s easy to read all this and feel caught between the need for speed and the pressure to release a polished product. But minimum delightfulness doesn’t have to mean scope creep and long development cycles.

You can raise the quality bar without delaying your product releases…and you should…

1. Start with delight in mind: From early planning and design, think about the emotional impact your product will have on users. When using some feature, what do you want the end user to feel? This doesn’t require perfection, but it does mean focusing on key moments that can delight users—whether through design, interactions, or quick wins. Prioritize those elements in early development, even if other features are still minimal.

2. Scrap quickly, build carefully: Use early, rough experiments to test your ideas (like June did), but don’t confuse those experiments with your actual product. Once you’ve validated your concept (say through iterative Figma prototypes), focus on building a version of your product that meets a higher bar of quality.

3. Polish selectively: You don’t need to perfect everything at once. Start by polishing the parts of your product that users will notice most. What’s the biggest surface area of your product that reaches the most people? That’s your biggest opportunity to leave a first impression. For example, focus on a seamless onboarding experience, clean user interface, and bug-free core functionality. Very small touches can raise the perceived quality of your product.

4. Invest in design early: If you’re a founder starting a company, hire a great product designer. Index very heavily on design as a first-class citizen—like Dovetail being a design-led company. And if you’re a PM, bring designers in as early as possible to your process to give them as much context as needed to think about how to add delight points.

5. Launch softly, iterate fast: Launching a polished product doesn’t mean you should slow down your feedback loops. It’s good to soft-launch to a smaller audience to learn some stuff, but users should never feel like they’re using an unfinished product.

🔑 Bottom line: “Good enough" just ain’t good enough! Delight matters more than ever, especially in early product versions where you’re trying to hook people in.

5. Going beyond metrics and truly caring

🫰 Why it matters: Metrics can only tell you so much about your customers.

🥇 Applying it: Build relationships better than anyone else in your market, and make yourself more accessible than any customer would expect. Then, be there and treat each one as a partner.

Let’s go deeper…

My buddy from might slap my wrists for this one…but metrics like LTV, NPS, NDR, or CAC are not the determinants of customer success.

These numbers have become the default for understanding customer relationships. But metrics can’t replace relationships. In fact CJ did say this: “I know I’m the metrics guy and all, but here’s something I believe: When the data and the anecdotes disagree, the anecdotes are usually right.”

Anecodates come from interactions and interactions come from having relationships. But relationships often get deprioritized because it takes far less time to pull up a chart that tells us if our customers are happy.

Be careful of the numbers.

As an analytics company, you’d be right to guess June is incredibly data-driven.

But as I spoke more with Enzo, it became clear that it isn’t numbers and charts that drive June—it’s their obsession with customer care.

Enzo set out to take a radically human approach to understanding and connecting with customers. What stands out most to me is how Enzo and his co-founder share their personal WhatsApp numbers with their customers, extending them direct, ongoing access to the founding team.

It’s not about 24/7 availability though—it’s about building genuine trust and a constant line of communication that feels personal.

This is amplified on June’s “Customers” page, where they share stories from their customers in an interactive WhatsApp-style chat. A very cool design pattern that shows the intimacy of these behind-the-scenes conversations.

Enzo says this approach is based on a simple principle: caring more.

As a startup, you always have the power to do three things:

1. Move faster

2. Take bigger risks

3. Care more

Only #1 is a variable of how much money you raise, meaning anyone from day one can choose to win customers by caring more than the competition.

For June, it’s a mindset that goes far beyond the transactional dynamics most companies fall into. Enzo sees every customer as a partner and makes their customers’ problems their team’s problems.

One way they do this is with a customer map.

"Download" your Customer’s Map

At the heart of June’s approach is what Enzo calls the customer map—an internal tool that helps teams understand not just what a customer says they need, but what truly motivates and challenges them.

June’s team doesn’t just collect data on customer behavior; they work to understand each customer’s individual goals, fears, pet peeves, and broader business context.

To build these maps, you need to listen deeply to get to know your customers as people, not just users. This is what makes their approach so effective.

So many teams rely on support tickets or feedback forms to speak to customers. But as June does, the teams who care more do so by keeping the conversations flowing, be it through Slack, WhatsApp, or some other dedicated channel. And better yet, give key customers access to leadership—this builds a ton of trust and shows that you’re there for them.

If you’ve ever watched Better Call Saul, this was how Kim Wexler won her first big client, Mesa Verde, from the big dog, Hamlin, Hamlin & McGill (HHM). She showed her 1:1 personal dedication to their needs, contrasting it with the impersonal nature of a large firm like HHM.

Besides using “care” to win business, maintaining this kind of access to your customer, selfishly, means you get continuous feedback that’s much more nuanced than a simple NPS survey.

🔑 Bottom line: True customer-centricity boils down to caring more, and using that care to build real relationships. Metrics matter, but parternships with customers matter more. These are the kinds of interaction that transforms customers into co-creators, helping shape the product they rely on.

6. Make your founders face your brand

🫰 Why it matters: The future of marketing is people-based, not brand-based. We trust individuals over companies, and startups that start putting an actual face to their brand have a massive advantage. June is Enzo. Enzo is June.

🥇 Applying it: Founders and their teams should invest in building personal brands and authentic thought leadership. Rather than hiding behind a corporate logo, put the people behind the product front and center. This builds trust, connection, and curiosity, and ultimately draws people to the product through the value of the content they see from the team.

Let’s go deeper…

Traditional marketing is losing its impact. The song “Distribution is what matters”, and “Distriburion is what’s becoming more expensive” has been played on repeat.

Looking at emerging startups like Athyna (with Bill), beehiiv (with Tyler), Carry (with Ankur), and of course, June (with Enzo), and one commonality is the founders brand is a key marketing lever.

In the past it was always and only about building the company’s brand. PR played a big part of this. But increasingly, building an audience first is what the cool kids are doing.

While that might have been unreliable in the past (because if building an audience was that easy we’d all be paid travel influencers), it’s becoming more achievable especially thanks to owned channels like newsletters.

These channels, including LinkedIn, are leaning a) person-centric rather than brand-centric, and b) story-centric rather than information-centric.

That work super well because it captures the founder’s personality. It humanizes the company. And it’s far more authentic and real than a logo telling you what’s going on.

In short, people heavily gravitate towards founders being honest, vulnerable, and humerous/light.

Instead of relying on corporate accounts and promotional content, Enzo’s posts focus on sharing actual value—insights, stories, and behind the scenes lessons from building June—without constantly pushing the product. Enzo sees his content as a means to build curiosity around the product and establish some level of being helpful before people head over to see what June is about.

If you ship it, post it!

What’s more, when you ship product regularly and you building in public, you’re flexing an absolutle growth superpower. By just telling people online what you’re shipping (because most companies don’t)…it’s an incredible way to show off your ability to execute.

It shows your momentum, and that will attract customers, talent, investors, and help motivate/retain your current team. Why? Because when people see you’re consistently improving, they start to to believe in your ability to deliver value long term.

Take Tyler Denk from beehiiv…this dude is a savage when it comes to using social media to build hype.

It’s all about reputation—a reputation for reliability and innovation, which feeds back into your marketing efforts.

For June (and these other new startups creating their own playbooks) every new launch becomes a moment to deepen relationships with customers and show that they are listening, adapting, and growing.

🔑 Bottom line: Use your face to market your product (softly).

Adios, muchachos🫡

And that’s a wrap on our June deep dive.

A small startup making very big moves. They’re definitely one of the companies I’m watching in this new era of emerging startups that are having to be more resourcesful in how to grow in these increasingly more crowded markets.

If you want to learn more about how June can help your company grow—if you’re selling B2B SaaS—and save time and money, you can learn more here. 🤝

If you have any questions for me or Enzo…drop them in the comments!

As always, thanks for spending time with me here today.

Until next time.
— Jaryd ✌️

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Friends, I just made my first startup investment. Today’s deep dive is a tad different, where I’ll share what stood out most to me about the company’s approach. My hope is that sharing this will add to your mental model and inspire some ideas to help you with your own product.

For example, have you ever heard of negative CAC, a strategy of constants, or using a suite of brands to sell your product? Yup, neither had I.

I learned this from Athyna.

Athyna helps companies grow their full-time teams by unlocking great talent in non-obvious emerging tech markets like LATAM. They get rid of the headaches that come with building a distributed workforce, they use AI to match talent and companies ridiculously fast, and they add tons of value to both ends of an important equation: They help companies save money, while simultaneously helping the people working there make more of it.

But that’s impossible, Jimmy!

When industries mature, growth slows. And when growth becomes more expensive, efficiency becomes the name of the game. Efficiency means sustainability, and that means founders need to obsess over healthier profit margins.

This is just how the world works. As my favorite economist, Noah Smith explained it; this is where we’re at with the tech industry since most things on the internet have now been built.

The result of this maturity and cost of growth is real…startup failures in the US have jumped 60% over the past year. Also, according to Carta, the bankruptcy rate of startups is 700% more than in 2019.

Ultimately, startups fail when they run out of cash. And in tech, headcount is by far the biggest line item—often accounting for ~70% of a company’s budget.

Athyna is in the business of bringing that number way down without compromising on talent quality. In a time of expensive growth, Athyna helps make it affordable again, giving startups essential extra runway.

That’s a bet I can (and did) get behind.

What to expect 🤝

The rest of this piece will unpack 8 new ideas on product, growth, strategy, and startup building I’ve learned studying how Athyna grows. Here’s a peek:

1. The power of embedded media companies

2. Creator-squad growth

3. A strategy of constants

4. Mind the shiny object

5. The cold email growth hack

6. The sidecar product trick

7. A simple, but hard, superpower.

8. Build what you can consume

20-minute read.

If you want to learn more about how Athyna can help your company grow and save on your biggest cost, you can learn more here or just book a call.

Check out Athyna

1. The power of embedded media companies

💡 Big idea: Modern media companies (e.g. NYT) have a software company embedded inside. But, next-gen software companies will have media companies embedded inside.

🫰 Why it matters: Embedded media companies can create negative CAC and turn lead gen into a profit center. And with growth becoming more expensive, founders who don’t build a media/creator strategy may struggle with it in the coming years.

🥇 Applying it: An easy first step is investing in your personal brand. Social media or starting a newsletter is a tool to grow your audience and therefore your business. Or, you could consider buying a small newsletter/podcast.

Let’s go deeper…

People were confused when HubSpot acquired The Hustle newsletter and the My First Million podcast. What business does a SaaS company have buying two media companies?

Well…

1. HubSpot wants to grow in the SMB and mid-market.

2. CAC through traditional marketing and sales here is very crowded/expensive

3. That CAC is only going to increase as those channels get more saturated

4. Newsletters & podcasts are good at building large and engaged audiences for very little cost.

5. Those SMB & mid-market decision-makers read/listen to The Hustle & MFM

6. By owning them, HubSpot drives brand value and can reach them for free

7. Bonus: These companies will keep making money to pay back the investment

Unpacked like that, it’s hard not to see the brilliance of the strategy.

And it’s clearly worked. Since then Hubspot has built the Hubspot Podcast Network which now has 34 unique podcasts all focusing on at least one of HubSpot's ICPs. They’ve doubled down on this “Own your own media” play and are hoping to find the next MFM early.

They’re not alone.

• Pendo acquired Mind the Product—a PM community and newsletter.

• RobinHood acquired MarketSnacks—a financial newsletter for consumers.

• Mailchimp acquired Courier—a business magazine

• Zapier acquired Makerpad—a no-code newsletter.

• SemRush acquired Backlino—a marketing newsletter.

By owning these embedded media companies, these software companies are all enjoying what Bill calls negative CAC through this channel and organically integrating their brand in extremely valuable, non-salesy, content.

It’s such a winning move.

And Athyna is doing exactly that with the Open Source CEO newsletter that boasts a wild 40,000+ subscribers and sold-out sponsors.

The only difference is Athyna didn’t have to buy it because it’s written by Bill! With every email that Bill is paid to send, his media co. drives leads to Athyna.

To build or to buy…

If you’re a bigger company wanting to break away from expensive channels, you’re probably best off buying one because you’re getting the right audience instantly, vs being distracted and having to build one yourself.

As Kyle Poyar says,"Big SaaS companies with billion-dollar valuations can afford to treat media acquisitions as experiments and as an insurance policy against uncertain future outcomes. They don’t necessarily need to build a comprehensive business case with board-approved targets in order to get the green light on an acquisition. These types of acquisitions haven’t been proven out yet among earlier stage (Seed-Series C) or more cash-constrained companies.”

But as Athyna and Bill show us, startups can also invest in their own, independently branded and run, newsletters or podcasts to feed their core business. For instance:

• PostHog has Product For Engineers co-authored by the team.

• beehiiv has Big Desk Energy by founder/CEO Tyler Denk.

It’s not easy doing this while running a company, but Bill has great advice on how to do it.

We now know software companies owning an embedded media company get free growth. Bill saw how well it worked, and asked a simple question, “How we can 10X this?”

Instead of buying more media companies, Bill’s genius strategy was to get many media companies to buy a part of Athyna. Let’s pull the thread on this below.

🔑 Bottom line: Owning your own brand-independent media company is like having another business that gets paid to organically drive excellent leads to your main business.

2. Creator-squad growth

💡 Big idea: Go beyond paid creator/influencer marketing. Create a group of creator investors that will keep shouting your name.

🫰 Why it matters: People want to buy from other people, not brands. But an ongoing creator program can be expensive. One way to indefinitely tap this growth channel and grow while your creators grow for $0 in cash, is by raising a mini round that is creator-led.

🥇 Applying it: Think about a few “influencers” in your space that likely reach your ICP. Then test a lead-gen campaign with one or two of them. Get some data, and then model out what ~10-20 creators could do for your growth.

Let’s go deeper…

Athyna’s latest funding round of $2.5M was mostly led by 15 creators. Myself included.

The combined reach of this group is well into the hundreds of thousands of unique people, with many millions of monthly impressions. As investors in Athyna, we talk about Athyna.

The data? 40% of Athyna’s leads are now coming through this channel.

And importantly:

1. They aren’t paying any cash for this growth, allowing them to invest in other channels and R&D.

2. As these 15 media companies grow (which conservatively is probably a combined 50-100% a year), this channel becomes more effective vs how others become more competitive.

3. This growth all compounds in SEO over time given all the content is evergreen, with mounting backlinks and increased domain authorities of these growing creators

4. The word-of-mouth flywheel will spin faster.

I’ve seen more and more companies have a creator strategy, but they’re all based on paying the creators via direct sponsorships or affiliates.

I haven’t seen one besides Athyna leveraging creators by getting them to pay the company to talk about them.

It’s negative CAC on steroids.

Somebody Give Bill a Bells! 🥃

But while this idea was Bill’s baby, I must give so much credit to the team who do an extraordinary job creating a community around this group of creators. I won’t give away all the behind-the-scenes secrets to this brand-new program because Bill might slap my wrists, but here’s one thing that stands out to me.

• What they do: Athyna offers to help us with content, research, sponsorship outreach, and facilitating collabs. Plus, we all share lots of insights with each other in Slack on how to grow and monetize.

• Why they do it: Athyna wants their creator investors to be as successful as possible.

• The outcome: Growth in their creators means growth to Athyna.

Everybody wins.

The universal idea is this: Don’t be shy about giving away parts of your company to people who can have a direct hand in helping you grow it efficiently and sustainably. That’s employees. It’s key customers or partners. It could be creators…

💡 Bottom line: Every growth channel is going to become more expensive to play in over time. Investor creators could accelerate your negative CAC strategy and drive steady leads.

3. A strategy of constants

💡 Big idea: There’s a Bezos philosophy around strategy: Always focus on the constants. This means invest in the customer needs and wants that will never change.

🫰 Why it matters: It’s very easy to get caught up adjusting a strategy based on hype cycles. And, while you don’t want to stop lifting your head to see what’s changing and spot possible inflections, you mainly should focus on defining and building upon the things that endure over time.

🥇 Applying it: Find time to map out what your market’s fundamental needs are—the timeless principles that are unlikely to change in the future. Then check if your strategy clearly improves those things for your customer.

Let’s go deeper…

You can probably think of at least 5 products that have added some AI feature that feels unnecessary.

These are trend chases looking to add the Sparkle emoji to their homepage. ✨

But Athyna has based their AI strategy on the idea of constants; an idea first introduced by Bezos.

And you can always go deeper on solving your users’ constant needs.

For instance, the constants for:

• My newsletter’s are

  • Quality, novelty, and relevance of insights

• OpenAI’s are

  • Accuracy, speed, and cost of model

• Tesla’s are:

  • Battery life and price

• Boeing’s are:

  • Planes that don’t have doors flying off…

If those companies improve their constants, people will love them for it and they’ll grow.

This is all quite neat for anyone who does “strategy” work. It’s almost a cheat code for what to say Yes and No to.

Athyna had a pretty good idea of what their constants were, but to be sure, they started with a needs analysis. They mapped out the functional, social, and emotional needs of their customers and ranked them against how important and often they occurred, as well as from a solution POV how big and crowded the market was.

“Once we had our needs analysis mapped we started building. All product and features pitches needed to map back to a user need from one of our three ICPs” - Bill

It looked like this.👇

In the end, Athyna had 4 timeless needs:

• Quality talent - who doesn’t want amazing people?

• Accurate role fit - who doesn’t want the most qualified candidates?

• Fast time-to-hire - who doesn’t want to find a fit sooner?

• Low cost - who doesn’t want to save the bank?

Bill sent me this table showing how Athyna amplifies these constants—where all the constants, but most obviously those of Talent, Process, and Speed are improved with AI.

The typical recruitment process lasts 3 to 8 weeks. By using AI to search tens of thousands of profiles (quality) from markets like LATAM (cost), rate and rank them against job descriptions and various recruiter-enabled assessments (process), and push the best suggestions to recruiters (speed), Athyna gets recruiters and best-match talent speaking within 2 days.

The end result of using AI to improve the constants is their epic new product, Athyna AI.

So, what are your product’s constants? And are you investing in them?

Because the more I think about the companies we’ve covered, the more obvious it is: The companies that (1) are super clear on what their constants are, and (2) always do R&D around going deeper on them, will beat the ones who have loose understandings of them and easily chase shiny objects.

More on shiny objects coming right up…

🔑 Bottom line: The constants in your business should always be reflected in at least one of the pillars of your strategy.

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4. Mind the shiny object

💡 Big idea: Shiny Object Syndrom is a very common trap. It’s that irresistible pull toward new ideas, strategies, or projects that promise instant gratification and untold riches.

🫰 Why it matters: SOS is anti-strategy because it’s a reflection of indecisivness. If you keep chasing after something new, copying because a competitor is doing it, or just saying yes to all things that come to mind, you won’t ever make progress.

🥇 Applying it: No should be the default answer to new things. Until the evidence is clear that saying Yes clearly intergates with your strategic choice set—Where To Play, How To Win—shut that shit (politelly) down.

Let’s go deeper…

I was recently watching Dragons’ Den (the UK, and original, Shark Tank) and I saw a sad case of an entrepreneur having no idea he had Shiny Objected Syndrome (SOS). You can watch the clip here, but in short, this dude had invented over 40 things in his life—of which not one had ever made any money. He was pitching a product to the Dragons for a biodegradable cable tie, but he was also (1) writing a novel, (2) inventing a parachute for NASA, and (3) designing a new type of surfboard.

Poor Simon.

No need to tell you he didn’t get a nickel that day, and Simon’s trajectory has been eerily similar to this chart…

• Focus x Execution = up and to the right.

• Distraction x Execution = sideways (or often down) and to the right

Simply because no company can be all things to everyone. Narrowing down the strategic playing field is an absolute must. One quick pulse check you can do right now is to ask yourself (and answer honestly), “What choices have we made that have narrowed our competitive field across markets, segments, channels, categories, and ICPs?”

The tighter and more obvious the answer, the more strategically focused you are.

When you haven’t made a decision about where you want to play in the market, then hopping around to “the next best thing” like Simon is an easy slope to slip down. But, even when you have made choices, chasing the odd distraction that pulls you away from that focus (like a Sirens Song) is still possible.

This happened to me at my own startup, and this happened to Bill and Athyna. They were ramping up and seeing good growth, and got caught in the SOS whirlpool for a bit. It’s much easier than you think to fall into.

Their shiny object was to become an Employer of Record (like Deel).

They shopped this around in 2022 with top VCs when they were raising a $5M round at a $25M valuation. And they got very close to making this happen. Right in the end, the deal fell through due to a conflict of interest.

I think that was lucky. If they’d raised the $5M then, they probably would have gone down the EOR path. A hard and competitive route up against an incredible startup—Deel—that wouldn’t have charted a clear path to winning.

They ended up doing a bridge round of $500k, focused on their matchmaking marketplace which grew at 22% MoM last year, and now do $6M+ ARR.

Focus pays quick and big dividends.

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The best way to avoid SOS is to know what choices you’ve made and say no like a mad man to the things that don’t align with where you want to play, and progress how you will win in that market.

Three quick notes from me and Bill’s experience…

• Be careful of cool new tech that may provide no real value to your customer

• Be careful of entering new markets just because they are there

• Be careful of chasing ideas from investor feedback or one big customer

💡 Bottom line: You won’t grow by simply doing more things and playing in more spaces. You need to know when to go deeper on what you have, vs going wider.

5. The cold outbound email growth hack

💡 Big idea: Athyna went from sending 50 emails per week to a scaled outbound machine sending 1.2M emails per week. They did this using a suite of different sub-brands.

🫰 Why it matters: Outbound is a volume game, but, it’s hard to send a lot of emails every week because cold outreach is always going to be slowed and limited by how “warm” your email domain is. The more unique domains you use, the faster you’ll reach scale (and the higher your ceiling will be).

🥇 Applying it: If cold email is part of your GTM, consider buying a related domain, feeding it into your email machine, and ramping up its daily sends.

Let’s go deeper…

Outbound email is still one of the best ways to reach B2B buyers. It’s a simple equation—send more emails to more of the right people with the right message, and you’ll land more customers.

But getting to volume takes time because it takes about 3 months to warm up a domain to send any decent number of emails. Which is fair—that’s how we get spared from spam. Send too many too fast, and you’re digging yourself a hole.

But Bill isn’t one to dilly-dally. He had little patience to wait and slowly scale the power of the single Athyna.com domain. So, he took a play from Dr. Strange and launched a full suite of sub-brands that can each send 100K emails a day—like the little email workhorses of Athyna!

It’s quickly become their biggest growth channel, with 60 million emails being sent a year. And doing some napkin math, at $6M+ ARR, that’s an ROI of $0.1 per email.

As Bill said: “I don’t think you need that many channels to really be working to get to a big business. For several years, outbound alone accounted for 80% of our revenue. We’re still a small company, so being able to do this at our current scale leads me to believe we’re probably the best in the world at it.”

FYI, Brett Adcock sold Vettery (a talent marketplace with Athyna’s model) for $110M with the same strategy. For 4-5 years outbound was the only channel he used.

To replicate a strategy like this, simply:

• Buy more (cheap) domains

• Connect them to your outbound GTM machine (i.e Attio, Apollo, Clay)

• Start warming them up and ramping your sequences that all point to your core product

💡 Bottom line: If you’re playing the outbound email game, increase your surface area of success by using multiple domains via sub-brands to run sequences.

6. Tactical sidecar products

💡 Big idea: You can build free mini-products (AKA sidecar products) that solve a general, high-frequency problem for your ICP, some of who will then convert to the core product thanks to well placed CTAs.

🫰 Why it matters: These products are like honeypots; attracting new users to the core product with a free (and valuable) hook. They are great for PLG motions!

🥇 Applying it: Find an adjacent, wider use case that's relevant to your core product and customer, and then build a free tool to attract them.

Let’s go deeper…

I first learned of the term “Sidecar Product” when reading up on Snyk, which uses multiple mini products like The Snyk Vulnerability Database and Snyk Advisor to contribute to noticeable platform growth.

These products are not core to Snyk’s product, but they are:

1. Free to use

2. Useful to devs

3. Related to Snyks primary use case of dev security

These micro tools help build brand awareness and funnel the right people to the main lead gen motion since they always place CTAs that send people to the core.

Athyna is using a similar strategy with Ava—their AI-powered Chrome extension for job seekers.

Ava does two things:

• For the market, it helps anyone looking for a job (1) build a great LinkedIn profile, (2) tailor their job applications, and (3) get job suggestions.

• For Athyna—by creating massive, free, and related value for job-seekers—Ava connects Athyna with the perfect supply side of the marketplace: motivated tech workers who are comfortable with AI. This helps them (1) grow the depth of their talent pool, and (2) is a brilliant data play, giving them first-party insight into real-world job market data.

The second sidecar product Athyna is working on is a third-party job board. Like Ava, this opens another big door to grow the talent side of the market. Also like Ava, it doubles down on their data play. By aggregating tons of usage-based data points, they can build a really solid model that shows the state of labor and can inform where Athyna should invest.

Bill likes to compare this strategy of adding 3rd party employers to how Amazon opened its marketplace to 3rd party sellers. He even scribbled over Bezo’s 2018 letter about it.

This will drive Athyna’s core flywheel, just like it did for Amazon. That’s the power of sidecar products.

So, it’s worth thinking about what you could offer the market as a complementary onramp to your main product.

💡 Bottom line: If you build a sidecar product, make sure it aligns closely with your market’s main problem/needs map.

7. A simple, but hard, superpower

💡 Big idea: Being incredibly helpful to others eventually helps you.

🫰 Why it matters: Actually being helpful is hard. It means saying Yes to things that don’t directly progress your goals and following through. But if you can do a hard thing that other people won’t—the rewards are very high. People reciprocate, and you’ll expand your surface area of opportunity.

🥇 Applying it: The next time you’re catching up with a buddy, coworker, customer, or investor, expliclty ask them, “How can I help you most right now?”. If the answer is doable—do it.

Let’s go deeper…

What I remember most about meeting Bill, besides how flipping cool he is (he’s run with the bulls, patted lions, and swum with sharks!) was seeing a founder building and growing his business in a way that I wish I had.

A trait I quickly came to see in Bill—one that I think is a true superpower that infinitely expands one’s surface area for success—is that Bill does not stop being incredibly helpful. I’m not exaggerating. And not surface-level help, like actually really caring about how he can add value to everyone in his circles. He also asks for nothing in return.

In a world where we want to say No more often to protect our focus, offering to help and delivering on that help is hard to do. But like we saw with Stripe, if you can do a hard thing that other people won’t—the rewards are very high.

I asked Bill about how he manages to be so helpful to so many people while running a $6M+ ARR startup and building a rapidly growing media company, and if he had any advice. Of course, he was happy to help.

💡 Bottom line: Help yourself by helping others.

8. Build what you can consume

💡 Big idea: The most successful companies use their own product to grow. “Never trust a skinny chef!”

🫰 Why it matters: When you rely on your own product as a tool to be successful, it aligns the incentives with your customers, drives crafstmanship and attention to detail, and gives you ongoing feedback from being your own power user.

🥇 Applying it: Dogfood. Dogfood. More dogfood.

Let’s go deeper…

The US job market is crazy competitive, and comp packages reflect that. What’s more, predictions suggest by 2030 there will be a talent shortage in the US, particularly in the tech sector. And when things become more scarce, they become more expensive.

Athyna’s entire shtick is that companies should be growing with remote talent from underutilized and growing tech hub markets. I believe about 80% of Athyna’s supply side is the LATAM market—that’s Argentina, Brazil, Mexico, and Colombia.

People often think offshore talent just means India or the Philippines. That’s because most don’t really understand that the tech ecosystem in South America is as strong as any other ecosystem in the world, outside of the US.

Consider this:

• The cost of living in LATAM is significantly lower than in the U.S. This allows companies to offer competitive salaries (up to 40-50% better than local rates) that are more affordable (up to 80% less than onshore) without compromising the quality of life. Simply, offshore is an opportunity to pay a premium to talent at a discount to you.

• Emerging tech hubs in São Paulo, Buenos Aires, and Mexico City are producing highly skilled professionals, coming from very mature tech ecosystems.

• LATAM professionals operate within similar time zones to the U.S., meaning significant overlap (6 hours or more) for collaboration.

• Establishing a presence in LATAM can open doors to new markets and customer bases, driving business growth.

And while Athyna helps US tech companies access LATAM talent and hedge against the 2030 shortage, they themselves are also their own customer and favorite case study—using Athyna to build their competitive edge. As Bill says:

Internally, we have team members that are ex-Amazon, Uber, Oracle, Meta and more. We’d not be able to afford that type of talent had we hired them in the US, Australia etc. All of our team gets paid much more than they would locally and we give RSUs (stock) from executives to interns. So everyone is super happy.

It still makes me shake my head that people want to hire their entire team onshore, whether that be the US, Canada, Aus, or the UK. Salaries are 3-5x higher in most cases, and as Founder & CEO I need to make the best decisions for our shareholders.
So I need to ask, "Will this marketing, sales, creative, product hire add 400% more value because they are boots on the ground in the US?”. And the answer is almost always a “Hell no”. So it would be irresponsible for me to hire in the US.

Of course there are some exceptions, boots on the ground enterprise sales and CS, events, some high level comms that we will hire local to our target markets in the future but that’s it really. We are creating a huge, valuable company, that we are all owners of today and the best way to maximise that is to avoid hiring in the US.

This was definitely a factor in my decision to invest. I believe companies that spend time using their own products and building for themselves just as much as they build for their customers are low-key awesome drivers of growth, as well as craftsmanship inside the product.

How could you not care more when you’re also a power user?

🔑 Bottom line: The more that you and your team use your own product, the higher the quality bar (and customer empathy level) will be.

Subscribe now

And that’s the end of our Athyna analysis. I hope you found this post helpful and enjoyable, and appreciated the Smart Brevity I’ve been practicing! 🙏 s/o to for putting that book on my radar.

Once again, if you want to learn more about how Athyna can help your company grow, you can learn more here or just book a call. 🤝

If you have any questions for me or Bill…drop them in the comments!

As always, thanks for spending time with me here today.

Until next time.
— Jaryd ✌️

Further study on Athyna… 🕳️🐇

• How Athyna Makes Remote, Work

• The life of a tech CEO in a rocket ship startup

• Interview with Bill about his side hustle

• Bill’s philosophy on stock and compensation

Hi, everyone!

There’s a universal truth that as users of countless software products, we can probably all agree with: Popups suck.

And—just like that party host who tries to show you around their new house, pointing out their gallery wall and all the nicknacks you don’t really care about—so do those 20-step product tours. Skip, thanks!

Even as someone who studies products and builds products for a living, I can’t close a popup fast enough.

But up until now, these annoyances have been somewhat of a necessary evil. An evil I’ve guiltily deployed many times across the products I’ve built for my users to probably rage click out of faster than Batman can disappear from a conversation.

This has been especially true for PLG products, where tours and popups are how product builders and growth teams drive adoption.

But, luckily for the world of software, in 2020 James Evans, Richard Freling, and Vinay Ayyala co-founded CommandBar with a key insight: Digital adoption products are a frustration-center because they push information to users.

Like all brilliant ideas, the solution seems so clear when you hear it. CommandBar pulls users toward information when they need it and turns user assistance into a delight-center.

The easiest way to think about what they do is like this: CommandBar allows product teams to embed an intelligent AI agent on top of their software to help their end-users perform actions, fetch data, and co-browse with them to show how the product works.

As James told me in our interview, it’s like having a friendly human assistant standing by your side who anticipates your needs. Copilot is a true successor to the antiquated tree-diagram chatbot— it’s just miles more personalized and helpful.

Through their comprehensive user assistance suite, CommandBar helps their B2B customers with all the vital parts of their own growth motions: Onboarding, activation, upselling, and retention.

Ironically, despite CommandBar being a sales-led company, they’re in the business of helping product-led companies do PLG.

That’s why my thesis is that CommandBar will win because they’re building the PLG-as-a-Service layer for the generation of companies scrambling to be product-led. In a way, like the strategy of selling picks in the gold rush.

And they’re already killing it. They’ve raised ~$25M, have hundreds of customers, are reaching around 25M end users, and are growing at 300% a year.

But, as we’ll see in today’s deep dive, CommandBar has found growth momentum by bucking the common wisdom that startups should create a category.

If you only have a few minutes to spare, here are some tactical things product builders, founders, and senior tech leaders can learn from CommandBar in just 5 minutes.

On growth 🌱

• One of the most impactful, lowest investment, and least risky growth levers is to make what you already have much better. While growth through “new” seems more sexy, you likely have much more juice to squeeze out of your existing product.

• Offering your audience unique and aggregated first-party data from the larger market is an incredibly strong carrot. Since CommandBar is a layer sitting across many PLG platforms, they are able to aggregate insights across many companies and share novel insights with their customers on how they can do PLG better.

• Product-market fit maps very closely to how repeatable your customer flow is. If your demand is fragmented and people want you for different reasons, then you're probably good at sales/marketing but might not have strong PMF.

• When going after your ICP, don’t stop at title. Push further into pain points, company structure, what other tools the company uses, etc. You need to go deeper and ask, “Are these the best folks with this title that we could meet?”.

• The quality of company-generated content is increasingly becoming a signal for the quality of the product and a whole-product differentiator. CommandBar has an insanely good blog—one of the best I’ve seen—and they told me that it’s very hard to make the 1,000-word post work these days. Either content needs to be very deep (their strategy…and mine), or very snackable. The “Content Written For Google” level stuff isn’t engaging, and to stay defensible in the Generative Search era, you have to optimize for people staying on your page.

• Tapping into sponsored podcasts and newsletters as a channel can be an incredibly effective way to reach your market. But, you need your audience and messaging— with a differentiated narrative and counter-positioning— locked in before you do creator-led growth.

• If your product is found through searching, and not discovery, then G2 reviews can be a strong source of leads. When products are evaluated by comparison shopping (like B2B software in a known category), G2 is the place where that happens. You need to actively ask and incentivize your customers to review you.

On strategy 🧩

• Disrupting an existing category is often better than trying to create a brand-new one. At least, to start. James said, “Every founder wants to be an innovator; building a new mousetrap the world has never seen and building a market before any competitors catch on. In most cases, I firmly believe that process is hard mode.” Easy mode is taking the insight behind your mousetrap and using it to disrupt an existing category by adding your own rules to a known game.

• You can always start in an existing category, and then once you’ve found success, pull the market into a new one you create later. Perhaps the best way to create a category is to go through a category.

• It’s possible to be so good that your customers want to show your branding to their customers. This is elite-level trust, and happens when you prioritize for the end user experience even more than your direct customer. Although, both usually win in this case.

• Interoperability is how you can make your product hard to replace. Embedded products win.

On product 💎

• When playing an established game, you can add your own rules by building a narrower version of what your competitors have, with just enough functionality to compete, that still preserves and highlights your core insight. This isn’t just about Tablestakes & Differentiators, but more so the opportunity to differentiate on table stakes and focus more on the outcome that the customer is looking for. You don't have to copy.

• It’s essential to align your AI pricing with your overall product strategy. You need to think about what outcome you’re trying to optimize for, and based on that, determine the risk-reward for capping usage.

• As much as possible, you want to focus on pulling, not pushing. It’s as basic as this: Listening and learning beats talking. Yet, many products don't abide by this fundamental law of communication.

• Another golden rule is this: Don’t annoy users. This starts by thinking about what annoys you as a user, then working backward to make sure you’re not forgetting to empathize with your own product’s users.

• James believes the theme of PLG has destroyed more enterprise value than it has created. To his point, PLG works once you’ve achieved PMF, but before then, being sales-led helps you understand why people are coming to you. Plus, the downside with PLG is that the motivation to talk to you is so low once people have access.

On startup building 🏗️

• Don’t overthink the mechanics of PMF, and dwell on the question: “Do we have it?!”. The focus should be solely on executing, speaking to people, and learning from what you’re doing.  

• The pitch deck is first and foremost for you as the founders, and investors second. “We’ve always been clear-headed that the most valuable asset in our company wasn’t the capital, but our time as founders. We looked at our seed deck as a memo to ourselves of why we - self-proclaimed smart people who could do a bunch of other things with their time - should invest the next decade+ of our blood, sweat, and tears into this company”, says James.

• Spending too much time on the design of your deck is a red flag. It shows you’re either prioritizing the wrong things or “you are trying to hide bad ideas with pretty slides”

• It’s a misnomer to think you’re not a good founder if you’re not doing deep work. James says sometimes the the best thing you can do— at least once you have PMF—is unblocking someone in 3 minutes vs an hour. He has days where he chooses to just do meetings and sit on Slack.

In today’s analysis, we’ll explore how CommandBar is reshaping what product adoption looks like as they seek to own the PLG-as-a-Service layer, as well as their contrarian Trojan Horse strategy for category creation. We’ll cover: 

1. Origins: Cmd+K; The Universal Search Bar. When CommandBar started as a single product company after an initial idea pivot, the founders had a strong opinion on what they wanted to bring to market—Cmd+k-as-a-Service. But despite getting into YC and seeing signs of early PMF, they realized creating a category was deeply overrated.  

2. Repositioning: The Gravity Of Markets. Starting in the late 90s, with Microsoft’s infamous Clippy, product builders have realized the importance of helping users learn and adopt software. That’s resulted in the commoditized Digital Adoption market with minimal innovation. CommandBar’s thesis is that these products suck for users and are ineffective for the same reason Clippy is dead: Pushing info to people is a flawed approach.

3. Product: Command(+K) and Conquer. To unlock growth, stop playing the game on hard mode, and show the market why CommandBar’s approach of assistance through pulling is right, James swallowed a hard pill and repositioned CommandBar to compete in the existing category. Within just 3 years, they’ve built an AI-powered user assistance product suite for product-led SaaS companies and are leaders in the market.

4. Playbook: Become the Gold Standard That End-Users Demand. CommandBar’s move has been to turn product adoption (a frustration) into user assistance (a delight). As a result, they’re following a similar path to products like Stripe and Plaid: Users trust these products so much, that companies want to show off that they use them. This is the ultimate awareness flywheel. And as it spins faster, the big picture is to pull their market once again, back into their own defined category.

Great! Hatch secured. All systems ago. Let’s begin our descent.

1. Origins: Cmd+K; The Universal Search Bar

Like so many incredible products, the idea for CommandBar came from the founders pulling the thread on an internal product they made for another startup they were working on.

James, Richard, and Vinay were buddies from college building codePost—a tool for computer science teachers to grade and drop feedback on student code.

Despite having no prior startup experience, the trio had a knack for product building. They were great at learning from customers and quickly iterating based on feedback. But, this led to a product with a lot of functionality where the learning curve continued to increase. As James said, this led to an important insight; one that would lead them to CommandBar.

We learned with codePost that shipping fast and being super responsive to user questions and feedback was a competitive advantage. We also learned that when you do that, your product can get complicated and hard to use quickly.
codePost became kind of one-size-fits-all but in a way that meant confusing-for-most.

Being the savvy builders they are—and hating the idea of intrusive popups and classic onboarding tactics—they came up with a solution to help users navigate around and get the most value out of codePost.

They made a terminal full of contextual shortcuts for their users, allowing them to teleport anywhere on the app without having to explore menus or figure out what to click.

I love how James describes it:

It was a “command bar” that allowed us to remove the entry points to a lot of features: instead of a button leading you to X, we could allow you to search for X. That way, any user could quickly find what they cared about, but the UI would never be cluttered or overwhelming. Basically this was a way to scale a UI but keep it discoverable. It also had the unexpected effect of increasing our product velocity; we could build narrow and experimental features without sacrificing any UX.

A true magic widget, all at the tap of Cmd+K.

It worked incredibly well. So well, that the founders started spending more time thinking about this widget than their actual product.

That's the biggest sign there is. Follow what excites you in the early days, even if you’re technically doing something else.

So they decided to turn their magic widget into a productized Cmd+K-as-a-Service startup, believing that other product builders would be facing the same problem they solved for themselves.

To a universal software problem, they incepted the idea of The Universal Search Bar. 🪄

CommandBar was born in the Spring of 2020, and the team started building cmd+k for any app during the Summer batch of YC.

Their core belief was that users spend too much time learning how to use new interfaces and that a search-first approach was simply better.

The first product gave teams the ability to configure the search bar so the default state could be personalized based on end-user attributes. For example, by user type, level of engagement (i.e. power users vs unactivated ones), and activity history within the product.

This is what the first product looked like, and how they packaged it in their seed deck.

Quick bit of advice I loved from James regarding this first slide of their pitch deck:

My biggest advice (and learning) from iterating on this slide is to be as clear as possible about what you’re building early on in the presentation. If you don’t, everything that follows will just lead to more confusion.

Today that first product, called Spotlight, looks like this. Still very true to the core concept, just 10X more powerful.

Spotlight was, and is, a window into any application. It allows people to see and go deep into a product without having to go anywhere.

At first, James positioned CommandBar as a brand new paradigm for interacting with software. A new category to disrupt the boring, annoying, and commoditized Digital Adoption space.

And rightly so, it was.

But educating the market on something different and selling your product in a newly minted category with no competition is hard for three obvious reasons:

1. Nobody has the budget for your new category

2. New categories are seen as risky, and buyers have a Fear of Fucking Up

3. When you create a category, you remove helpful reference points

Nonetheless, they had real traction. But traction can also be like a Siren’s song—pulling good sailors into the sea if they're not careful.

Signs of promise in the eye of the category creation storm

In the year after YC, their universal search bar was spreading faster than they expected.

They were winning nice early customers and adding great logos like Gusto, LaunchDarkly, ClickUp, and Netlify. All inbound, I might add. This pushed them quickly toward $1M in ARR, and powered them through their Seed and Series A rounds, raising $25M in total.

To many founders, they’d go home singing at this point about finding product-market fit.

But not James. He saw this as a false summit in their journey to PMF.

At this point, he was doing all the selling. And despite closing deals, what he realized was that each deal won felt very different. As he put it, “Each company thought we were something different. And our buyers were very disparate. We had leaders from Product, Engineering, Growth/Marketing, and Customer Support/Success.”

• Some thought CommandBar was a power user shortcut tool

• Some thought CommandBar was a dev-tool-specific alternative to onboarding

• Some thought CommandBar was a way to reduce support tickets

To James, product-market fit maps closely to how repeatable your customer flow is. I’d read that sentence again because that’s golden wisdom.

Does everyone who wants to use your product have the same problems, and get excited about the same features? Or is everyone a bit different and using your product randomly and asking for features that don't really make sense? If the latter, then you're probably good at sales/marketing but might not have strong PMF.

— James, via a Reddit AMA

So, seeing the traction but realizing it was fragmented traction, James and the team made a big positioning decision, based on two additional observations, that led them to broaden their narrow product sooner than they thought. 

1. Their customers wanted more ways to influence their end-users, especially the ones who didn’t have intent yet.

2. The more they studied how influencing users without intent was being solved, the more they saw a huge opportunity in the established category.

CommandBar decided to join the larger market and play the easier game—except, they brought along their own set of rules.

What do they look like now?

2. Repositioning: The Gravity Of Markets

To understand why CommandBar’s product is so necessary, let’s take a moment and pay our respects to any early internet user’s long-lost frenemy.

Never forget Clippy, “The fucking clown”

In the early ’90s, most people had never touched a computer, and almost half of America had never heard of the Internet. Plus, the small circles of people that were using them were interacting through command-line interfaces.

So, it’s easy to see how the concept of navigating software and using things like menus in a GUI was a foreign concept to many people.

That’s why when Microsoft was pushing their PCs into the home, they knew they’d need a strategy to break down the adoption barrier and make it easy for non-technical people to learn and use their software.

Their first idea to make people more comfortable with computers in their homes was to make navigating a computer like being in your home. They did this with Bob.

Instead of icons, menus, command lines, and lengthy documentation; a user’s computer was modeled to look like a home. It had a front door when you’d sign in, and various rooms around the house (like one for Office) with things you could click on to open up applications (like Word). And importantly, you’d know about all this stuff thanks to some anthropomorphic assistants at the bottom right corner.

The obvious hope was to create a vibe of familiarity.

Except, people hated it, and Bob was shut down in ‘96. But the concept of an onboarding character lived on…

…one of them being that know-it-all, googly-eyed, paperclip.

“Would you like help?”, repeated Clippy on loop.

Clippy—which was nicknamed “The fucking clown” internally at Microsoft during the development of Office—was one of the most frustrating user interface components in computer history.

If you were writing a doc, Clippy would chime in.

The idea here was sound. Clippy would theoretically show up during the moments Microsoft thought you’d need an extra hand and walk you toward the relevant action. This was the first real pass at consumer-centric digital adoption. But, Clippy ground people’s gears for a few reasons.

1. He lacked any personalization. Clippy had no idea who you were or what you were trying to get done while using Office. He just made assumptions, and with those assumptions, told you what to do.

2. He didn’t care to learn. Clippy had no user context, but he also never asked you anything to try to gain some. He didn’t know how to listen.

3. He was invasive. Whether you needed him or not, Clippy had a knack for interrupting you. Maybe you didn’t need help, or maybe you were focused and didn’t need help now. Either way, he’d come raising his brows at you.

4. He infantilized the user. Power users comfortable with Office didn’t need an animated paperclip to tell them what to do.

He was eventually snuffed out for his flaws. But, his legacy lives on—nudging people towards action with pushed information is how companies still try to flatten the learning curves of their products.

That’s because the same underlying problem still exists: software products can be hard to learn and use.

Unfortunately, most companies who carry his torch are building on the same premise of how onboarding should be driven.

More Clippy’s…

All you need to know is that the Digital Adoption category is made up of all the products offering in-app tools designed to help with product adoption, feature adoption, and reduce user friction as they learn some new app.

These are the popups, checklists, tours, pulsing hotspots, help widgets, etc you can find across companies like Appcues, Pendo, and Userlane, or as home-grown internal tools.

Sometimes these things can be helpful, but only—and I say this generously— sometimes. They’re better than Clippy, sure, but most of the time we all still try to close them as fast as possible.

Given such a common user behavior, it’s surprising nobody latched onto that problem besides James. As he said when recounting where the idea for CommandBar came from.

The status quo for reaching users in-product was largely interruptive pop-up messages. As users ourselves, we always found these rather annoying and closed them quickly. Turns out, this was increasingly the case for our customers as well – declining engagement rates because of growing user fatigue with pop-ups that they were trained to expect to be unpersonalized and unhelpful.

This slide from CommandBar’s seed deck shows how they viewed the market:

It’s very easy to agree. Their hypothesis was that the most user-centric tools aim to personalize experiences by comprehending user intent and refraining from inundating the user with company-centric information that they may not find relevant.

This means fewer generic popups and more tailored guidance.

Fired up with this thesis, CommandBar’s first strategy against the entrenched and crowded market of Digital Adoption was to create their own pond and position themselves as a new category of software. As James said:

At the time I felt like the only startup "worth" starting was something novel that wasn't just an incremental improvement on something that was already in market. Since then, I've come to appreciate the gravity of markets. Selling something great into an existing market is 10x easier—it's easier to find buyers, it's easier to explain what you do, it's easier to justify budget, etc.

Luckily, as we already touched on, James knew to see through the early PMF signals they were finding in this new pond.

He was not going to be the founder who missed the forest for the trees.

Switching to easy mode

James put it this way, and I couldn’t agree more: Startups are never easy, but you don’t get extra credit for making it even harder.

And building a category is certainly making it harder. When we spoke, he told me that it might be faster to get to $1M in ARR as a category-creating startup, but it’s much harder getting to $5M-$10M a year. That’s because you have to cross the infamous chasm and find your market beyond early adopters.

And there is no harder mode than chasm crossing. Whereas when you find a way to be noticeably and measurably better than the status quo in a market, you skip this level. And the status quo very clearly sucked for both sides: companies struggled to generate more than sugar-high increases in engagement, and annoyed end-users immediately closed the pop-ups.

Who needs to build a new category when the conditions are just perfect for category disruption: unhappy customers for expensive, low-performing, products?

The inflection point for CommandBar came when one prospect said this to them: “If you can replace Pendo for me, I can buy you. If you can’t, it’s going to have to wait a year.”

This time, they leaned into “yes”, and James repositioned CommandBar, hopping them outside of their own little pond into the bigger Digital Adoption one. Cheekily, they rebranded the category they joined to User Assistance—symbolic of how they wanted to compete against the myriad of mediocre products. Basically it was them saying, “Fine, we’ll play your game, but we’re going to play it on our terms”.

Baller.

When we repositioned, we no longer had to explain why what we did was useful. Product teams already know what product tours and surveys are for.
Instead of taking 25 minutes and multiple customer examples to explain what we do (like in category creation hard mode), it now often takes two minutes. “We’re evaluating digital adoption vendors and came across you because of your unique approach.” Great. Qualified. That’s easy mode in action. We even had people adopt our wording and ask specifically for user assistance.

— James

This move doubled their growth rate.

It’s also a move we can all learn something important from: the market always wins.

While making something new and designing a category is the latest trending flavor, it’s not the only way. Sometimes founders need to follow the pull of the market and the path that already exists instead of holding onto their original assumptions.

[Repositioning] made it’s easier to explain what we do to potential buyers, but also people in our lives — family, friends, etc. Along with the signals that this strategy was working, this change made everyone feel better and more proud of what we’re doing. “We’re replacing shitty popups and chatbots” (easy mode) is a lot clearer than “we’re building this search bar thing” (hard mode).

Now that we know what game CommandBar is playing, let’s see the new rules they’ve introduced.

3. Product: Command(+K) and Conquer

After pond hopping—which mechanically involved (1) a marketing & positioning exercise, (2) a new product roadmap to move quickly from one to many products, and (3) an updated GTM motion—it became clear they were finding PMF on the ascent of the true summit.

Here, momentum was picking up and they finally felt the pull of demand. The product-market fit signs they saw were:

• They started being able to reliably drive demand. Blog posts drove leads. Conferences drove leads. Sponsorships on Lenny’s Podcast drove leads. And all the leads looked similar, vs disparate like the first time.

• Their customers started to repeat their unique messaging to them. “I found you on ___ and it seemed like you had a different solution to user onboarding that was more intent-based.” The key was that people would use their own words, like how they rebranded the category to user assistance, during conversations. This proved what they were putting out there was resonating with people.

• The first 10 minutes of every discovery call had a very similar feeling. Despite selling to a variety of personas (Support, Product, Growth, Marketing) and covering a variety of use cases (ticket deflection, activation, engagement), a very similar pattern at the beginning of calls emerged.

Expanding on that last note, James has an excellent point:

Before our positioning change, we were reaching product, growth, marketing, and CX people. After our positioning change, we were still reaching product, growth, marketing, and CX people. BUT, we were reaching people in those departments who (a) had immediate pain that we could solve and (b) knew something about what we were offering. This made a HUGE difference. The repeatable point here I think is that you shouldn’t stop at “we’re reaching folks with the right title”. You need to go deeper and say “are these the best folks with this title that we could meet”.

Same game, new rules

There are many big-picture levers that a company can pull on to grow. For instance, new growth can be charted based on:

• A market penetration strategy. This involves increasing market share for existing products by selling more within the current market.

  • Example: Coca-Cola running more ad campaigns to sell more Coke to current customers.

• A product development strategy. This involves creating new products to sell to existing markets.

  • Example: Apple creating the Apple Watch to sell to their existing customers.

• A diversification strategy. This involves entering a new market with a new product.

  • Example: Amazon moving beyond ecom and into cloud computing with AWS.

• A market expansion strategy: This involves entering new markets with existing products.

  • Example: Starbucks rolling out into new countries

It’s the famous Ansoff Matrix for growth bets:

But, what this chart fails to show is probably one of the most impactful, lowest investment, and least risky growth levers there is: making what you have much better.

This point was made perfectly by in one of my all-time favorite reads of Lenny’s: How to accelerate growth by focusing on the features you already have

In my experience, you can drive significantly more growth by focusing on getting users to engage more with your existing key features and user flows

In other words, if you get your core product and experience wrong, no matter what new features you tack on—you just can’t grow. At least sustainably.

And that’s the growth lever CommandBar puts on a silver platter: their product helps their customers grow by removing end-user frustration, creating delight, and amplifying their existing product.

It’s the same game other Digital Adoption players are trying to play. But, the big experience difference with Commandbar is that by having an AI-powered guide standing behind each user, it’s like having a well-trained-to-your-preferences human butler for everyone without all the cost and overhead of maintaining a live team.

It’s the deepest level of personalization you can get with an onboarding product that I’ve seen, allowing their PLG customers to craft very individualized ramp-up experiences for their users.

Going back to “the fucking clown”, CommandBar’s approach to user assistance took a lot of inspiration from Clippy’s shortcomings. In their autopsy of the paperclip, they came up with a few rules that differentiate them in the market.

These 4 rules are also nice generalized product-building principles.

Rule #1: Pull, don’t push

Unlike Clippy's intrusive approach, CommandBar is all about user-initiated interactions. It’s about surfacing relevant assistance when people need it, rather than having “help” forced upon them in the wrong moments.

Most onboarding tactics push content to users. The “take a tour”, “click here”, or “watch this” prompts. This always means people will see some stuff they don’t care about and will struggle to find some stuff they do care about.

That’s why CommandBar focuses on pull. Pull means giving users some way to tell you what they’re trying to do, then using personalization to give them the lowest friction path to getting that job done.

Listening is a superpower.

Rule #2: Learn from user actions

Because CommandBar uses pull and allows users to specify what they want, they’re getting direct input from users that CommandBar then stores as search logs, allowing product teams to learn from intent.

This becomes very interesting data that you can turn into personalized outreach for upselling, relationship building, or roadmap ideas.

Rule #3: Help users avoid distractions

Clippy would happily interrupt you while you were working. CommandBar is all about minimizing distractions and keeping users in flow.

And the main way they do that is by keeping users inside the product.

This is important because as we know, CommandBar is for PLG companies. And the entire point of this model is self-service. And self-service means people are learning about a product on their own time. And doing something on our own time means we can easily get distracted for a gazillion reasons.

That’s why activating a PLG user on their first session is so important. CommandBar is designed to optimize for this by making sure nobody has to navigate to anything outside of the product or even the page a user is on.

In other words, with CommandBar there are no potential offramps.

Beyond all the content and actions being served in-app, CommandBar goes a step further by pointing people toward the most useful subsection of content that matches their query, whether that’s a sentence in a help doc or a video clip. This is very useful for distraction avoidance and just shows how much they value the end-users time.

Rule #4: Guide rather than interrupt

Alerts just annoy people, plain and simple. Up to 78% of users have reported deleting an app because of notification fatigue. You can probably think of a few apps that overdo their push strategies, which as CommandBar points out is unfortunate since when timed correctly, they can actually be helpful.

Therefore a big part of CommandBar’s suite is tools that intervene at the right moments. This is necessary because you can’t totally rely on users telling you their problems—a platform needs to make smart deductions. For instance, if you’re rage-clicking around or are navigating in a way that the AI picks up isn’t achieving anything and is predictive of confusion, the assistant can offer help: “Were you trying to do X?”, or “You seem confused, see this guide that explains more about Y!”

CommandBar’s answer to “intervening at the right moment” is their AI-guided Nudges product.

With it, CommandBar makes any action nudgeable, where you can tailor a nudge based on user attributes like:

• How new is the user?

• What type of user is this?

• Have they used this page before?

• Does this user’s past behavior (including mouse movements) suggest they are confused?

• On other sites that use CommandBar, does this user tend to like support content?

That last point alludes to a very interesting strategy that we’ll cover when we get to CommandBar’s playbook. 🤐

The product breakdown: The PLG powerup store

The CommandBar platform is like a candy store where PLG companies can go and find ridiculously delicious and helpful product powerups for their growth motions.

Each feature has a clear standalone value, but the more of them you use, the more of a value multiplier effect you’ll be able to give to your end users. Simply, CommandBar is going for the bundled platform play: To be the only tool PLG companies need to drive continuous onboarding.

And the way they’ve bundled this store is very interesting, with all components working together to wash the hands of the others. In short, their product is made up of:

• Nudges, for proactively suggesting experiences for low-intent users.

  • This offering bundles form functions like tours, announcement modals, surveys, banners, and checklist/questlists. These are all the neutralizer features to compete in the existing category and become a replacement for tools like Pendo, except, these are flexible, non-annoying, and crafted with finesse for the end-user experience.

• Copilot, for actively providing experiences that respond to high-intent users asking for help.

  • This is where CommandBar has their truly differentiating features. There’s HelpHub, Spotlight, and by far their most novel feature: Copilot. Copilot is their AI-powered assistant who can help users do almost anything, including answer questions, perform actions on the user’s behalf, as well as co-browse with them to show them what to do. Copilot learns about user preferences (like reading to learn or exploring to learn) and is trained on user and business goals as it develops its assistance strategy per user. It’s also available on mobile.

• A game-changing user model for tailored onboarding.

  • The premise of CommandBar is personalization, and they deliver on that promise with unique segmentation criteria, as well as control features like

    • Rate limits, where you can choose to limit the number of product tours, announcements, and surveys your users will see in a given period.

    • Rage clicks, where you can choose to display a nudge whenever your users seem frustrated and are repeatedly clicking an area on your product. This is one of the many behavioral triggers available.

    • Strike rate tracking, where you can track users who seem annoyed based on how many times they've rapidly closed a nudge. Their analytics then makes it easy to experiment with your nudges so you can improve your strike rate.

• Simple and actionable analytics.

  • The dashboard shows you everything you need to know about how users are interacting with your CommandBar instance. From here, everything is measurable and optimizable.

• Relevant integrations.

  • Obviously you can plug your tools into CommandBar with built-in integrations. No code required. This, along with stuff like admin controls and security, are their tablestakes—the basic expectations for an enterprise-ready SaaS product.

How their AI pricing strategy supports this

Figuring out how to price an AI product is tricky. There are two camps really:

• Usage-based pricing

• Value-based pricing

Rather than directly tying their AI costs to usage, CommandBar's approach leans towards value-based pricing. They correctly recognize that the true value of their AI features lies in their availability. This strategy contrasts with a usage-based model, which very much like having an hourly lawyer, can create uncertainty for customers and potentially misalign incentives.

CommandBar folds their AI pricing into their flat-rate subscriptions. It’s one and the same. And that’s essential because CommandBar has two things that must be true for them to execute their big picture strategy (which we’re about to unpack):

1. CommandBar must be consistent: For Copilot to help, it needs to become the go-to for users. Building that trust requires consistently answering user questions so well it resolves the issue they came for.

• CommandBar must be ubiquitous: Using Copilot won’t become a habit for users if it’s only available on certain pages or for certain topics. Only if Copilot is ubiquitous across their customer’s products will it become their default help solution.

These are the insights our pricing flows from: If we shut down Copilot because our customer ran out of AI credits, it’s no longer consistent. And if customers worry about API usage, they might limit Copilot to the hardest to understand parts of the product. That’s why we landed on a simple subscription: It’s the easiest pricing model to provide Copilot’s value.

— James, via How we priced our AI SaaS product (and the mistakes we avoided)

Plus, by bundling their AI features within existing pricing tiers, CommandBar reinforces the idea to customers that Copilot is an integral part of their product's value, not a separate add-on. Their killer differentiator is never limited.

Of course, there’s the risk of abuse and losing money when you’re charged variably but you’re offloading that cost to users at a fixed price. CommandBar clearly believes the benefits of value-based is greater than the risks of usage-based, but they do have two safeguards in place to prevent catastrophic anomalies.

1. Rate limiting based on Monthly Active Users (MAUs)

2. Monitoring usage to identify and address unusual surges

Something to noodle on when considering how to charge for an AI product.

4. Playbook: Become the Gold Standard That End-Users Demand

In this final section of today’s deep dive, let’s talk about strategy. These are the 5 things that really stood out to me in my research.

1. Their trust strategy

2. Their interoperability strategy

3. Their hard-to-replace strategy

4. Their Trojan Horse strategy

5. Their sales-led strategy

Let’s review.

What Stripe and Plaid taught us: It’s possible to be so good that your customers want to show your branding to their customers

The moment they’re given the chance, most companies hide the branding of any vendors they’re using for end-user-facing products. Beyond that, many companies will only choose software if that’s an option.

It makes sense—you just want your branding on your app. Why have another company’s logo embedded on your site, especially a company that you’re paying?

Of course, as the providing company, it’s wonderful having your little “Powered by Us!” copy being flaunted around the internet. You get to enjoy the embedded flywheel, where your product is marketed to your customers’ network of users.

Example: If CommandBar sells to 1 company, but that company has 10,000 customers, CommandBar’s effective reach is 10,000. That’s free broadcast advertising.

Unfortunately for most of the products that have this type of amplified reach, their branding gets disabled, limiting the power of the embedded flywheel.

CommandBar is in the same camp, given users on higher-tier plans can remove the branding. The question becomes, can CommandBar show their customers it’s more valuable to keep “Powered by CommandBar” on?

I believe they can.

Very few companies have managed to do it, but Stripe and Plaid are top-of-mind examples. When you see Stripe or Plaid, you trust a product more. I personally don’t want to use any financial product that requires account connections if it’s not done by Plaid. And I’m far more likely to buy some product if it runs on Stripe because I trust Stripe.

Stripe and Plaid have created specific layers in the financial ecosystem that are often more trusted than the products using them.

CommandBar, as the onboarding layer for many new SaaS products, has a rare opportunity to enjoy something similar.

What CommandBar needs to sell to their customers is the power of this familiarity effect. The pitch is simple: When people see CommandBar on your site, they’ll have more trust as they know how to get around and get things done.

When you achieve something with CommandBar, it feels good because the time between intent and action is short. So you want to use it again. And not using it is like ordering something on Amazon and not getting free-2-day shipping: it just feels subpar.

— James

So, just like how walking into a party with a bunch of strangers is infinitely more comfortable when you arrive with a friend, CommandBar can unlock something similar by allowing users to try a new product with their AI assistant.

Next, let’s look at one thing that will make this sell much easier.

The interoperability of a user’s preferences

Aah, interoperability!

If you don’t look at this picture and immediately hear Mark preaching why “Interoperability” is the future of the metaverse, then you may have been under a rock circa the time when Facebook changed their name.

Anyway…what is interoperability anyway?

In short, it means that one product or system can work with another product or system for information exchange without a user having to do anything.

Remember what I pointed out earlier…

On other sites that use CommandBar, does this user tend to like support content?

That is very revealing of a brilliant strategy in the works.

CommandBar’s killer pitch compared to the rest of the market is that each user has a personalized AI assistant who learns about them and can help them get stuff done.

But how annoying would it be to have an assistant that forgets everything about you when you go somewhere else? Very!

That’s why CommandBar is building to be interoperable across applications. If you use CommandBar on Jira, and then sign up to Amplitude, your Copilot will be at the ready, knowing things like how you enjoy tours vs reading, or that you’re a user who often needs to set up admin roles. This just feeds into why end-users will trust new companies more when seeing CommandBar—they know their butler is there.

This is brilliant, and it means CommandBar can sell compounded value to new customers because they can essentially say: “Don’t worry, even if you don’t know anything about your users yet, we do.”

Any PLG company wanting to help their users find value ASAP will see the insane value of this.

This is also a virtuous cycle: The more users rely on CommandBar, the more search and usage data they feed it. This creates a better CommandBar experience, which means they rely on CommandBar more. Repeat. 🤝

Be hard to replace

Once a customer has embedded and is using CommandBar, it’s jarring for their users to take it away. It’s a layer that can be styled to feel native, and end-users who are accustomed to having a command palette and assistant could easily be annoyed having their trusted sidekick removed.

James put it nicely:

I often joke with our customers that turning off CommandBar would be like asking their users to stop using Google search and go back to Yahoo Directory. It just makes the old building blocks feel old.

CommandBar obviously delivers a ton of value to their direct customers, but there’s a special type of lock-in they get to enjoy because of how much value they deliver to the end user.

It’s almost an insurance policy on churn. Similarly to how no company that values their designers would ever cancel Figma because all the designers would leave. 🤷

Power to the end-user.

Their Trojan Horse of category design

We know CommandBar started by trying to create a category and then switched to easy mode—wedging themselves in an existing category.

But, as Fat Joe iconically says: Yesterday’s price is not today’s price! ✊

What that means in our context, is that CommandBar is creating a ton of value right now in this existing market. They’re finding PMF. They’re building brand loyalty. They’re becoming hard to replace.

What was hard mode yesterday is not necessarily hard mode tomorrow. Tomorrow, CommandBar will have a lot more market power and cachet—cachet they can use as leverage to pull the market into a new category.

In short, I think their arc looks like this

Pull → Push → Pull again

It’s super smart, and a great example of James playing the long game. Because when they eventually do pull their market into a new one, CommandBar will get to reap the benefits of being Category King.

The power of being sales-led (and two tips from how they do sales)

The latest wisdom (at least for the past few years) is that if you’re not running a product-led motion, you’re missing out. All the snazziest companies are doing it, so why not run the same growth strategy?

The playbook, as we’ve seen across many companies covered so far, is to start with PLG and then layer on product-led sales.

CommandBar initially thought they’d follow the same path as the Notions of the world. But they ended up deciding to go against the grain, and James told me it was one of their best decisions.

Outside of the hard numbers like average. deal size increasing by 34% and their conversion rate going up by 17%, being fully sales-led allowed the team to:

1. Speak to far more customers (you get to learn and sell at the same time)

2. Have much more successful onboarding (ironic, I know, for a company selling onboarding automation)

Sales brings a high-touch approach to working with customers, and before you have PMF, James believes it’s a huge mistake to not have as many interactions with your customers at the beginning of their journey with your product as possible.

CommandBar runs a sales motion for small startups all the way to enterprise. Nobody gets self-service. What’s more, CommandBar doesn’t even list their pricing publically…every call to action is to Book a Demo.

Of course, they tested this and found it weeded out low-intent users from their pipeline. It also means the customers they acquire always activate and find value, meaning they’re prioritizing building a very strong customer base who have very low rates of canceling.

Two actionable things stood out to me around how they sell.

1. Every demo is personalized to the prospect. In the early days when James ran sales, he’d spend about an hour learning about each company and creating a personal Loom video showing how CommandBar would work for them. This is still a key part of their sales process.

2. They built a Chrome extension that visually shows CommandBar working on potential customers' own websites. This makes their product tangible to people, vs theoretical. Just like how people love hearing their own names more than any other sound, companies love seeing their own products being used as examples vs some “demo store”. Show, Don’t Tell.

For the curious, here’s their sales stack.

On the topic of sales, here’s one last bit of advice from their GTM leader, Joe Skupinsky, shared by Finn Lobsien:

He also told me about mistakes many sales leaders in startups make. He cited two main failure modes.

• First was not having a process. Startups are flexible, but that doesn’t mean you can just wing it. Without a reliable process you’re wasting time by starting from scratch each time. You also lack the ability to diagnose problems: If prospects constantly drop off during the trial stage, you know where to improve. Without process, you’re in the dark.

• The second failure mode was not preparing for meetings. Even if you’re not a founder, customers need to trust you. As Joe told me: “People will be averse to buying from someone who doesn’t have their shit together. People want to buy from people they feel confident about.”

You can find more details on how they sell here.

I’ll leave you with one parting thought. It’s rare to see a company try their hand at category creation, find success with it, yet still push the rudder in another direction to rather go head-to-head in a market where the players are fairly entrenched.

But the way CommandBar has done it—by bringing their own set of rules and POV to the game—they’ve brought exciting new blood to a stagnant category. That’s a GTM strategy more people should give consideration to, because as James minced no words in reinforcing with me—category creation is very hard.

Lastly, if you’re a product builder, growth operator, or founder running a PLG motion, you likely see the immense value potential CommandBar brings to the table. They’re building the onboarding layer I expect to see more and more PLG companies embedding above their products, and you can get in early :)

Schedule a demo. See how it could work for you. Onboarding in the best way.

Learn More

A huge thank you to James Evans and Finn Lobsien for making the time to speak with me, and to the CommandBar team for writing one helluva company blog. Without which, this piece would have been far harder to write.

I’ll see you all next time for another voyage down deep.

—Jaryd

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Many companies have ambitious missions that aren’t taken seriously.

Someone comes up with a nice sentence that checks the boxes of a rallying mission, slaps it on a deck, and reminds the team that “This is why we’re here!” at the company all-hands.

But, the puck often stops there.

That nicely crafted mission statement often fails to trickle down into plans and a team’s daily actions, and it remains an ambition that collects cobwebs.

How likely a defined purpose is to get realized is a complete function of the founder, and how the founder operationalizes the team around them in building a purpose-driven company beyond just in theory.

From researching many of the greatest companies, one pattern I’ve seen that’s a strong proxy for success is:

(Ambition of Mission X Feasibility of Mission X Uniqueness of Mission)^Founder's ability to drive Execution 

And hitting every note of that equation is Australian unicorn, Dovetail.

Dovetail’s mission is To Improve The Quality Of Every Thing.

Incredibly ambitious. And, you might be thinking that sounds unrealistically ambitious—like a derivative of the wishy-washy “Let’s make the world a better place”. However, what do you think the outcome of effective and applied customer research is?

The answer is higher quality products, which often meaningfully improve our day-to-day lives.

So, when you consider that Dovetail is the platform that helps product builders consolidate and understand scattered customer research data through analysis, synthesis, and summarization—in turn, creating a qualitative insights hub that enables them to drive compounding value and continued impact from their investment in research—it’s easy to see how that mission is actually realistic.

Dovetail will improve the quality of every company that uses them because Dovetail helps them find themes and actionable insights in their most important information haystack—customer insights. AKA, they play a crucial role in helping their customers find their next big chess move.

Try it. Find out what to build next!

And pushing that mission is one of the most impressive, humble, and inspirational founders I’ve had the privilege of speaking with: Benjamin Humphrey. Here’s how he views their mission.

Brad and I look to other companies that focus on making quality and enduring things like Pixar, Apple, Spotify, Steinway, and Rockstar Games, and the impact this focus has on the world in terms of driving innovation, creating lasting experiences, and improving lives. Quality things create a more enjoyable, less frustrating world. Quality things last and are enduring.

‘Improve the quality of every thing’ is a moonshot. Moonshots move the world forward. They are challenging. They require smart, passionate teams to succeed. “We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard; because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one we intend to win…”

Founded just 7 years ago, based on the thesis that there were plenty of tools that helped you to build something, but no tools that helped tell you what to build, Dovetail has already made incredible strides in creating their own category of software.

And while they have a few competitors now, in the last few minutes of my two calls with Benjamin for this piece, I saw a founder light up like never before when talking about their (actually) game-changing strategy for this next phase of their growth. We’ll get into what that is soon, but as you read this analysis, consider what you think the “Holy shit” 10X play would be to place customers at the heart of every organization. 🤯

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Trying out a new deep dive format…

I’ve approached this new HTG format with a lot of thought, but your feedback made it much easier. For example, most of you are here because you want to “Level up your growth/strategic skills to apply at work”, and when I asked you to rank what topics you care most about…here’s what hundreds of you said:

So, I’ve prioritized my time for you exactly in that way. Now, you’ll get the widest coverage of the areas you’re most interested in (i.e. the practical growth and strategy stuff) with less focus on insights from the startup story. Here’s how I’ve done it.

• 5 things you can learn from their growth levers

• 4 things you can learn from their strategy

• 3 things you can learn from their startup story

• 2 actionable ideas from their product

• 1 quote to leave you with from Benjamin

Each section will start with a bullet-style summary for the high level, with a deeper analysis below. If you’re in a rush, you can skim the snapshots at the top.

Here’s my goal with the new style:

• Cut to the chase. Don’t risk burying the lead.

• Make it easier for you to read in one go, with a more scannable component added so you can easily dig deeper into the sections and ideas that stand out to you

• Make the ROI for your time higher by packaging the same level of insight/analysis (if not more) into a shorter read

Sweet. With the housekeeping behind us, let’s get cracking.

Note: If you haven’t heard of Dovetail before, take a quick look at their very strong hero page for context as I’m jumping right to the growth/strategy stuff.

Five actionable lessons from their growth levers

🏊‍♂️ The bullet TLDR...hit any link to skip to the deeper/longer version 

• There is a secret to growth—it’s that reliable growth isn’t complicated, and it comes from the less flashy stuff. If you want to grow, the best tactic is continuous compounding which results from tweaking and optimizing the little things—and doing that regularly and fast.

• When there are noticeable inflections in growth—they mostly come from shipping new differentiating features. And Benjamin emphasizes this key point: Don’t wait too long to add your second product. Dovetail finds ideas by specifically going to their ICP users who don’t convert, asking them what’s holding them back, and then doing those things. 

• You need to layer on top-of-funnel marketing acquisition channels very proactively. Don’t get complacent with WOM and organic growth. Every single source of new users is a finite stream, and the flow of people coming in will always taper off. To keep increasing your traffic, start thinking right now about what the next stream is that you can test.

• You ensure growth throughout all types of macro conditions by not siloing yourself into selling to one type of customer. Also, by investing in being enterprise-ready sooner than you think. Dovetail focused on building a horizontal platform that doesn’t depend on the success of other startups, or within a specific industry.

• Opting users into a premium/reverse trial by default is diminishing the quality of your PQLs because users are not making an explicit choice to try your paid product out. Dovetail has found that intention matters a lot, and their CVR and LTV increased when users made the choice of when to start their trial period at a specific trigger.

🤿 Going deeper on these ideas...

💡 Luckily, growth isn’t about hacking, and it isn’t complex

Wanting to spend time on high-level strategizing is natural because it’s a lot of fun thinking of chess moves and game plans. But growth (especially for earlier-stage companies doesn't come from the "plan-plan-plan-build" model that often tries to find silver bullets that will change your growth trajectory.

Dovetail’s growth has mostly come from systematically figuring out what their main levers are, and then quickly prototyping core features or growth initiatives to optimize each lever. It’s about launching them to a subset of users, obsessively tracking key metrics, and not waiting for perfect data to make decisions.

If an initiative shows a signal of promise, Dovetail doubles down and iterates. If not, they kill it. This is the rapid Build > Assess > Build model for growth where the goal is to compress this cycle into days or weeks, not months.

It’s simple, but not easy.

To spot and squeeze the most juice from your growth levers, start by mapping out your entire user journey, from acquisition to retention. At each stage, identify potential levers—these could be improving landing page conversion rates, optimizing onboarding flows, SEO, or enhancing core product features to drive engagement. Then, prioritize these levers based on potential impact and ease of implementation. Finally, attack them methodically.

For each lever, brainstorm multiple optimization ideas with folks, prioritize the top 3-5, and if you have enough usage, run quick A/B tests. Remember, even small improvements compound over time: a 5% lift in conversion at each stage of your funnel can result in massive overall growth.

This approach of constant tinkering, massaging, and execution has taken Dovetail, by and large, from the theoretical strategy work to driving tangible, measurable growth.

💡 Find your next step change in growth by building your on-the-fence users’ unaddressed need

Dovetail has found one of their best sources of product ideas to be gap analysis with their pool of free users who meet their perfect customer profile criteria. AKA, the people who use Dovetail, should be paying, but for some reason are not.

Folks often have the right thinking here, but end up looking too much in the wrong pond— churned customers.

On-the-fence users are a much better source than churned ones because churned people are notoriously hard to ever win back since they are the ones who have actively tried your product, and then decided it wasn't for them.

Fortunately for Dovetail—since the Dovetail product is the fastest way to understand your users— they get to dogfood their own product to spot the themes and decide which things are the most important to build for them.

And when I asked Benjamin about growth inflections, his first answer (as covered in the point above) was that real growth isn’t about inflections—it’s the boring and methodical stuff. But his second answer when I pressed a bit was that closing the “I don’t upgrade because of this” gap was how Dovetail grows most consistently.

Often PMs get ideas by speaking to customers. That’s important, but ultimately you’re building for your existing paying customers. The resulting growth will come from retention, better WOM, and possible upselling. But if you want more noticeable and immediately measurable growth…build for your “should covert if we do this” market.

Each new feature Dovetail builds for a segment of free users becomes a new hook-line-and-sinker to convert a bunch of users to paying customers. And as Benjamin said, once you have PMF with your main product, the best time to start adding your second product was yesterday.

For example, by investigating and understanding one group of free users in the early days, Dovetail spotted that despite being a tool for the research persona, product managers were organically trying the product out. Listening to them helped Dovetail to widen their aperture both in positioning and product functionally and expand their TAM.

By stacking these features together, Dovetail quickly became the place that centralized scattered research functionality, addressing a shared pain point for user researchers and product teams. For example, they integrated magic transcription, theme clustering, channel analysis, and stakeholder presentation features into a single platform.

“Dovetail instantly reduced my workload from 100 hours down to 10 to share out customer insights.”

— Eric Liu (Product Manager at Notion)

Related to releasing high-quality products at a quick cadence, one of the big unlocks Benjamin shared with me was how Dovetail has created a culture where leaders remain hands-on and close to the product. When hiring for managers, they only bring on "player-coaches" who will both mentor and contribute to daily work as individual contributors—working high and low. This makes sure decision-makers have a deep understanding of the customer base and product capabilities, and he’s found one of the biggest mistakes is when managers don’t get their hands dirty and own certain initiatives as ICs.

💡 Exponential growth is a myth. Growth is quadratic, and it comes from adding your next acquisition channel while your current one still runs hot.

Dovetail is an excellent product, and people talk about excellent products. However, Benjamin told me they got a bit complacent and comfortable with the free growth they were getting from word of mouth.

The rate of growth you get here will eventually stagnate. That’s just how the timeless cycle of growth goes. Every channel matures and flatlines.

To keep growing at a steady or accelerating clip and to diversify out of pure organic, Dovetail started stacking growth channels strategically, recognizing that growth is typically quadratic rather than exponential.

For one, they invested heavily into SEO and content, seeing significant results and growing to hundreds of thousands of unique visitors monthly with a current 15% month-over-month growth rate. Dovetail has built a robust content pipeline, leveraging outsourced teams to dominate search results in their niche. They also create incredibly high-quality authoritative content that positions them as thought leaders. Just check out their The New Yorker style magazine for product managers—Outlier. It’s so good, with such informative content.

They’ve also layered in growth programs around community and tapping influencers. For instance, collaborating with creators (like me for this piece) and hosting events like the Insight Out conference to build IRL community engagement to augment their Slack community. Finding influential voices in your industry and developing partnerships to expand your reach is a great move to push that One-To-Many growth.

Bottom line: every channel you have—and every feature— will taper off in its effectiveness. The sooner you think about what you can sequence next, the sooner you can think about what to sequence after that to keep yourself climbing the hill at a good pace.

Go deeper on this concept: The Elephant in the room: The myth of exponential hypergrowth

💡 Take caution being the startup that sells only to other startups. Be antifragile by selling to harder customers.

For pretty much any B2B startup, everyone starts down market by selling to their founder friends. That’s the YC playbook: Sell to your cohort buddies > Sell to your cohorts buddies buddies.

It’s great for early acquisition and quick wins because startups are easier to sell to. But it doesn't help you build an antifragile business, as quite simply, you have an inherently fragile customer base.

And it’s increasingly volatile when economic conditions tighten. When startups face budget cuts or go under, your customer base can rapidly erode.

Instead, consider the tougher but antifragile approach: targeting larger, more established enterprises and diversifying your customer base across industries.

Not only does this strategy bring you more stability and push your product to meet higher standards, but finding product-market fit in larger, more complex organizations can lead to exponential growth.

Dovetail leaned into this and embraced enterprise readiness fairly early in their journey, dedicating about a year to being prepared. When I asked Benjamin about it, he said they did it because the market naturally pulled them upwards, since that’s where the need for an insights hub is most acute—large enterprises with fragmented feedback channels and siloed functions. For instance, Dovetail is crushing it with:

1. Banks and airlines (traditionally data-rich but insight-poor industries)

2. Non-software businesses undergoing digital transformation

3. R&D-heavy organizations with substantial budgets

This move not only increased their average contract value, but also built resilience into their business model and made it easier to acquire mid-market startups (great social proof).

Remember, the path to crazy value often lies in solving the hardest problems for the most demanding customers.

Here are a few ideas to diversify your own customer base:

1. Explore new vertical-specific solutions within your product

2. Adapt your marketing and sales approach for different industries (AKA widen your aperture)

3. Build partnerships in untapped sectors to gain footholds

💡 Free trials don’t offer enough time to build loyalty. Be overly generous in your free plan.

If you look at some of the most successful B2B companies, you’ll notice that they’re often the most generous with their free plans.

Generosity can be a powerful growth lever.

It allows you to capture the bottom of the market fully, even with users who aren't ready to spend yet. Dovetail is a great example of this principle. They offer unlimited users, transactions, AI features, and transcription hours in their free plan, with the only limitation being one project. (A great example of a Pricing & Packaging page)

This approach serves a few purposes:

1. Word-of-mouth growth: Free users become advocates, spreading awareness organically.

2. Future champions: Today's free users may become tomorrow's enterprise decision-makers.

3. Market domination: Capturing tons of free users creates more “on the fence” users that they’re able to analyze for growth opportunities.

Benjamin also told me it might be time for folks to rethink the default reverse trial—where everyone starts with premium and is downgraded to freemium. The problem with opting everyone into a trial is that they're not making the choice to test it out. There’s no intent, and the people who may only need the free features today are given all the (unneeded) bells and whistles. So, being downgraded isn’t an issue, but they’ve used their opportunity to trial premium later when they may actually need paid features.

Dovetail has found the most success when they trigger a trial when users attempt to access premium features, ensuring high intent and increasing conversion likelihood.

So much success in fact, that they’ve doubled down on maximizing Product Qualified Leads (PQLs) by offering self-service enterprise trials. A brilliant move, because:

1. It makes it easy to spot serious intent folks, as users willing to explore enterprise features are more likely to convert.

2. It provides great data, as usage patterns during enterprise trials offer a ton of insights for sales teams.

3. It removes friction, as self-service trials allow potential enterprise customers to evaluate Dovetail on their own terms.

Think of it as "progressive profiling", where it helps Dovetail gather user information over time rather than all at once.

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Four things you can learn from their strategy

 🏊‍♂️ The bullet TLDR...

• Don’t go deep where others are already swimming—but make sure to integrate and embed yourself there since that’s where customers already are.

• A solid approach to creating a category-defining product can often be boiled down to combining the value/JTDB of two very different products from different markets in a surprising (but obvious) way. For example: “We’re building <Some company from X category> + <Some company from Y category> for <Some type of person> doing <some type of specific job>”. In Dovetail’s case, they’re building VSCode + Github for people doing user research.

• Your AI strategy should intersect three things: Improving what your customers will always want improved, piggybacking on where you have a clear data advantage, and doing what AI is obviously better than humans at right now. Anything else is a goose chase that will cost you money, distract you and your customers from your real product, and create no competitive edge.

• A design-led product strategy is one that has the customer and their needs firmly at its center—and one that breaks down ambiguity. Dovetail, a design-led company, uses wireframes as a medium for communicating strategy instead of marketing or sales data because they better represent what the customer experiences.

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🤿 Going deeper...

💡 Strategy starts by establishing what you don’t want to be and do. Because only then can you create a new game to play.

Research is a big job, with many needs scattered across the full user journey. It looks something like this…

Dovetail consciously decided not to go into research collection logistics like scheduling, surveys, or usability testing. Instead, they focused on becoming the central hub for extracting insights from collected data.

Essentially, going deep on just this part:

This strategic exclusion—which they wrote about in a great public memo—allowed Dovetail to:

1. Avoid red oceans in adjacent, highly competitive spaces

2. Focus resources on their core value proposition

3. Create clear differentiation in the market

4. Avoid feature bloat and decreased usability

5. Lower complexity taxes and maintenance costs

They still bundle a ton of value inside that part of the loop, but they stay smart about it and have avoided the mistake of slipping into unnecessary and distracting markets that no doubt have tempted them.

And where they don’t tempt to bundle, they integrate with the purpose-built tools for data collection, rather than building these features themselves. This means they have greater extensibility, where they gain exposure to other platforms’ customer bases (e.g. on the integration stores), and also make their own product more valuable, since Dovetail’s flywheel is really data ingestion.

Three actionable takeaways here.

• Audit your product roadmap. Are you spreading resources too thin by trying to compete in adjacent spaces? Consider narrowing your focus to dominate your core value proposition.

• Evaluate your product's feature set. Are there areas where integrations with best-in-class tools could provide more value than in-house development?

• Map out your product's potential expansion paths. Which horizontal moves could capture more of your users' workflows without diluting your core value?

💡 Innovation often comes from connecting existing dots in a new but intuitive way

People often think innovation is coming up with something brand-spanking new. Something never seen before.

It’s increasingly rare for that to ever be the case though, because most things have been done before.

Far more commonly, innovation has nothing to do with reinventing the wheel. It’s about spotting patterns, connecting the dots, and slicing up/combining existing products to create something new.

And just like a chef who builds their creative brand on the shoulders of all dishes that came before them, you too can design your own category of software by fusing ideas from disparate markets that once taste-tested, just make sense.

Take Dovetail, they’re “Building VSCode + GitHub for people doing user research.”

From this, we can grab a formula for ourselves:

<Product from X category> + <Product from Y category> for <ICP> doing <Specific job>.

Consider these examples:

1. Airbnb: Hotels + Craigslist for travelers seeking authentic local experiences

2. Uber: Taxis + GPS-enabled smartphones for urban commuters needing convenient rides

3. Slack: IRC (Internet Relay Chat) + Modern UI/UX for teams requiring efficient communication

These often unexpected pairings (until they’re done and seem insanely obvious) create a unique value proposition in the market and also help you establish clear reference points in your customers’ minds.

If you’re like me, you’ve never tried Sushi-Pizza before, but just by its X+Y, you know exactly what to expect. And you know it’s going to be damn delicious.

Regardless of the scale you’d like to reach, we all want to create category-defining products. If nothing else, it just seems much more fun to make a new pond vs swimming in someone else’s.

So, let me leave you with this light/fun advice. It’s more about playing around with the goal of cross-pollinating ideas and thinking outside the box. But as they say…you must fuck around to find out.

Basically, just find some time to use the formula "<X> + <Y> for <audience> doing <job>" to brainstorm potential products. But spend most of the time with the X + Y part. Throw ideas around until something sounds interesting.

If you want to expand on a combo, then you can layer in the latter part of the formula and start building a compelling story around your idea that highlights how it bridges a previously disconnected need.

💡Don’t get caught in and contribute to the AI echo chamber by adding GenAI just for the sparkle emoji. Use it quietly to 10X your primary loop.

Dovetail's approach to AI brings us a great framework for using LLMs in your product:

1. Improve what customers always want better and already value most (Faster, more accessible insights)

2. Leverage your unique data advantage (A vast repo of customer feedback)

3. Focus on tasks LLMs excel at: (Processing and making inferences from large volumes of info)

4. Focus on human-in-the-loop features (I don’t want AI replacing my task, but augmenting it)

Dovetail spent a long time understanding their customers’ views on GenAI and how they felt about using it in their workflow. They actually got 3 independent studies run to avoid any biases.

Only then, once they understood all the limitations of AI, their customer's most pressing concerns, and the biggest unlocks AI could bring to their market, did they pragmatically start building any AI.

Here’s what they’ve built so far that has eliminated the grunt work, and helped surface more insights faster.

These Magic features have already been incredibly helpful for their users. But their biggest value so far has been setting up the board for Dovetail’s next huge strategic move: Personifying the voice of the customer, and bringing the customer’s voice into everything.

When Benjamin was talking about this vision, I was just blown away.

Dovetail, in short, plans to give every one of their customers a virtual version of their customers. An AI character trained on every customer interaction. Every piece of feedback and data point in an insights repository, ready to chime in during any meeting, Slack conversation, or decision-making process.

Quite literally, making the voice of the customer on-demand for everyone within the company. Imagine augmenting a product team's understanding of their customers in real time. When you’re ideating some feature, instead of asking “What would the customer think?” and guessing, you literally just make sure your virtual customer is turned on and they’ll tell you. Dovetail sees this character extending everywhere, including as a Zoom participant who sits in on calls.

Also, this character could be a reviewer in Figma; able to leave your team feedback when asked.

It’s an AI strategy that so perfectly piggybacks on all of Dovetail’s strengths and drives their core loop. It brings the power of context everywhere and to everyone—surfacing insights where it matters most: where the work is happening.

Who doesn’t want to be closer to their customer?

Guys, this is going to be a true game-changer. Get in now and start “training” your character, trust me! 🤣

Damn. I need this!

💡 Most companies you know are not building strategy in Figma, but tangible design is one of the best ways to align people on a vision.

Dovetail is a design-led company. They don’t have PMs, designers make decisions, and they emphasize the vitalness of design across their entire company.

Ironically as a PM, I love that. It puts user experience so high on the priority list, and that’s what people end up loving at the end of the day (assuming you solve a problem for them)—craftsmanship and good design.

One way this manifests itself at Dovetail is in a really unique approach to strategy planning: they use wireframes as the primary medium for communicating product strategy.

Most companies rely on dense documents filled with marketing data and sales projections. But Dovetail has a different POV— these often fail to capture the essence of the customer experience.

So, by leveraging wireframes, they create a tangible representation of their vision that resonates across all levels of the organization. There are a few clear benefits:

1. Better alignment: Wireframes provide a common visual language that bridges the gap between strategy and execution. Everybody sees the same thing.

2. Improved buy-in and engagement: Visual representations make it easier for stakeholders to understand and engage with the proposed strategy. A design says a thousand words.

3. Faster iteration: Low-fidelity wireframes allow for quick adjustments based on feedback.

4. Two for one: When you design the strategy, you also get a headstart on designing a new product.

These are good reasons why to do it, but this is not financial advice. You should be cautious trying to implement a design-led strategy as it’s quite a process change and can be jarring. However, you can steal parts of it in an easier way. For instance, the next time you’re planning on building a feature, start by creating a mock landing page for it. It’s like Amazon’s Working Backwards idea, but with design.

This forces teams to articulate value propositions clearly and think from the customer's perspective.

However, if you do want to go big with this, bear in mind the need to strike the right balance between high-level vision and necessary details in wireframes, as well as keeping the focus and making sure discussions center on strategic decisions rather than visual design preferences.

Three lessons from their startup/founding story

 🏊‍♂️ The bullet TLDR...

• Find a way to make your monthly updates—which you should be doing—unique. Dovetail used them as a storytelling vehicle, vs a way to update people. Narrative building is one of your biggest levers in the early days to rally support.

• Your job and best leverage as a leader is to define the rules of the game, and then let the players play it brilliantly.

• Take extreme ownership of your challenges. Talk about them publically, and get the team thinking about them. It’s uncomfortable, but trust in leadership is built by talking about the hard stuff that many people often already sense.

🤿 Going deeper...

💡 Storytelling, not numbers, is how you sell your product in the beginning

Metrics, KPIs, and growth charts are not what’s going to make your investors and team truly believe in your vision.

One of the things I found most interesting about Dovetail’s early days is how Benjamin flipped the script on traditional founder updates. Instead of bombarding stakeholders with spreadsheets, he turned their monthly communications into compelling narratives that kept building momentum in an ongoing story.

Here's why I think this story-based approach is so brilliant, especially for earlier-stage companies.

1. Context is king: When you're creating a new category, explaining what you're doing and why it matters is crucial. Numbers alone can't capture the nuance of your mission.

2. Vision over vanity metrics: In the first five years, Dovetail focused on storytelling over quantitative reports. This allowed them to paint a vivid picture of where they were headed, not just where they'd been.

3. Transparency builds trust: By sharing board meeting notes and founder updates internally, Dovetail created a culture of openness. This wasn't just for investors—it was about aligning the entire team with the company's vision.

4. Evolution, not revolution: As Dovetail grew, they didn't abandon storytelling. Instead, they evolved their approach, combining data-driven slideshows with quarterly long-form essays. This hybrid model satisfies number-crunchers while still delivering the narrative punch.

5. Deep dives drive change: Benjamin transformed their all-hands meetings from status updates to TED Talk-style deep dives. By focusing on a single topic—be it product strategy, threats, collaboration, or vision—he turned these meetings where people notoriously have their cameras off and do other stuff, into catalysts for meaningful change.

Here's how you can implement a similar approach:

1. Write monthly long-form updates that read like essays, not reports.

2. Include key metrics, but don't let them dominate the narrative.

3. Share these updates widely within your organization to drive alignment.

4. Use all-hands meetings to explore big ideas, not rehash day-to-day operations.

5. As you scale, find the right balance between data and narrative that works for your audience.

Remember, your job as a founder isn't just to build a product. It's also to sell a vision.

💡You always want to find out what your biggest levers for change are—and there are always only a few big ones.

As a founder, your most powerful role is that of a game designer. You set the rules, define the vision, and establish the cultural values. But once you've laid that foundation and told everyone what game is being played, your job shifts to letting people play it, and focusing on identifying and pulling other big levers for change to keep the game going.

Quick aside: Overall, a company can grow by quickly pulling lots of levers and compounding the impact. But as an individual, you’re much more limited. You need to find out what your 10X levers are that move the needle, and then regularly audit your activities and ask, "Is this one of our my 3 levers for growth?" If not, deprioritize it.

Benjamin gave me a few examples of levers leaders should think about.

1. Activate your team

Your team is your most powerful lever, but only if they're aligned and motivated. And to motivate, focus on fostering intrinsic motivation by:

• Giving people high degrees of ownership

• Connecting work to customer impact

• Encouraging craft mastery

2. Be explicitly clear

Never underestimate how explicit you need to be about expectations, goals, and strategy. It’s the foundation of alignment (which is a lever). For instance, be crystal clear about:

• Design standards

• Quality expectations

• Personal expectations

• Go-to-market decisions

• Cultural values

3. Leverage your management layer

Don't shoulder the burden of communication alone. You need to activate your management layer to cascade messages and reinforce strategy. This creates a multiplier effect on your communication efforts.

One thing Dovetail now does is hold regular "locker room talks" with managers to align on key messages and strategies to reinforce with their teams. This way Benjamin isn’t doing that at the all-hands where people are checked out, and lets managers talk to their reports more actively.

4. Avoid the internal trap

Beware of getting caught in the sauce of internal politics and busy work. As you scale, it's easy to become disconnected from real customer problems. Fight this tendency relentlessly by auditing your calendar monthly. If less than 50% of your time is spent on customer-facing or product-improving activities, make some changes.

5. Build a bigger rudder

Your job as a leader is to increase your company's ability to navigate change. This means building systems and teams that can adapt quickly to new information and market shifts.

One thing you can do is implement regular retrospectives to spot areas where your team is slow to change or adapt. And if you realize there are people on the team pushing the rudder the wrong way, you need to let them go.

💡 Humility, transparency, and being very honest with yourself are how you get everyone to spend time thinking about the right, highest-impact, things

While it might seem risky to air your dirty laundry, the most successful leaders are learning that being ruthlessly honest about their problems isn't just cathartic—it's a powerful lever for growth.

Transparency isn't just about sharing good news. Obviously, that’s easy. It's about creating a culture where problems are seen as opportunities for everywhere to put their heads together and problem-solve.

Benjamin is a great example of this. In this excerpt from a company update, notice how he didn't mince words about the challenges Dovetail faces:

We have more competition: startups nipping at our heels; the continued advancement of successful horizontal products; and new, existential technology threats like AI, which have the potential to completely upend our business. We also face many tactical issues which threaten to distract us and slow us down every single day, including technical debt, slow builds, long meetings, process overhead, missing data, missing peer feedback, and a struggling self-service business, to name a few.

This level of candor might make some of us uncomfortable, but it's precisely what sets great companies apart. Updates like that do a few things:

1. When everyone understands the real challenges, they can align their efforts to solve the most critical problems.

2. Openly discussing issues sparks creative problem-solving across the organization.

3. Honesty, especially about difficulties, builds credibility with your team

4. Transparency creates a shared sense of urgency to address problems

If you need a reminder about the cost of opacity:

1. Nokia: Leadership refused to acknowledge the threat posed by smartphones, leading to a catastrophic loss of market share.

2. Theranos: Holmes' refusal to be transparent about technological challenges led to fraud and the company's implosion

3. WeWork: Neumann's lack of transparency about the company's financial realities resulted in a failed IPO and massive devaluation.

In each case, a lack of honesty about the true challenges stopped the company from mobilizing to solve real problems.

Just remember this. Your team is likely already aware of many challenges, and addressing them head-on builds confidence in your leadership.

It’s about honesty + optimism. 🤝

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Two tactical ideas from their product and building ethos

 🏊‍♂️ The bullet TLDR...

• Make sure your unique and category-differentiating feature is at the forefront of your product, otherwise, any growth effort is lipstick on a pig. Be careful of The Growth Team Trap, and don’t over-index on your neutralizer and tablestakes features in the UI.

• Help your prospective customers sell your product to their stakeholders with a built-in, top-of-funnel, proposal/presentation builder.

🤿 Going deeper...

💡Make your product’s differentiator the centerpiece

You need to make the important things important.

Yea, of course, Jaryd!

Obvious advice, but so often, we don’t. And when it comes to your product's UI, you need to make your killer feature obvious. The moment you have popups and pulsing arrows pointing people to some feature, you have a product failing.

Benjamin categorizes features into three types:

1. Differentiators: The wow-inducing features that should be showcased ASAP.

2. Neutralizers: Features your competition has that you need to cover.

3. Table Stakes: Basic expectations that shouldn't dominate your roadmap.

For Dovetail, editable video transcription with sentiment analysis was their first differentiator. It was their initial aha moment, but at first, it was missable.

Benjamin told me that only recently did they start redoing their design to really put their differentiators center stage because at first, they fell into what let’s call The Growth Team Trap. (hmm, decent title for a piece…👀 )

It’s a common mistake—you rely on growth teams to paper over core product issues. If your growth team—or you—are adding popups, tooltips, and wizards to explain your product, you've already lost the battle. Lipstick, folk!

True growth comes from product-led initiatives, not marketing band-aids.

A few takeaways:

1. Categorize your features into the three buckets above, then review your UI. Is your differentiator immediately obvious to people?

2. Evolve thoughtfully. As Dovetail learned with their AI features, even differentiators can become distractions if not carefully integrated.

💡 Help your prospective customers sell your product to their stakeholders

One of the bigger challenges in B2B sales is helping your champions sell your product internally. To tackle this, Dovetail built a Proposal Builder.

It’s so smart. After hitting “Build a proposal”, users go through a Tinder-like swipe through of relevant things they care about in their buying evaluation. Below I’ve shared three screenshots of the feature.

The output is a beautiful deck, custom to that business’s needs, that lives on a landing page and can be downloaded as a PDF. Importantly, it doesn't just list features—it tells a story of value.

It’s a tactic that does a few things:

1. It empowers their champions. Don't just sell to your users—arm them to sell for you.

2. It puts lead qualification on autopilot. Each proposal built is a goldmine of information since it reveals the specific needs and pain points of potential customers, effectively conducting sales discovery without a single call.

3. It aggregates market intelligence. As proposals pile up, patterns emerge. Which problems do enterprises care about most? What features are deal-breakers? All invaluable data. Consider how you can create similar feedback loops in your own product.

It’s such a brilliant example of how you win in SaaS: by making your customers' success inseparable from your own.

You should try it out, at the least to see the experience.

👉 See how the proposal builder works (2 minutes)

One quote to leave you with from Benjamin

The biggest unlock has just been not taking things personally.

When you start a company as a founder, you're so invested in the success of the business. It's super easy to take everything personally - when someone quits, when a customer churns, when we lose a deal. You're just so personally invested because you built this thing from scratch.

But I realized that ultimately, Benjamin the person is actually different from Benjamin the CEO. At work, I'm kind of role-playing the CEO and being the person that people want me to be. That's not somebody who gets defensive or emotional when things go wrong.

The biggest unlock for me was realizing that even though I founded the company, it's still a job. People have certain expectations of me as the CEO that I need to live up to. That sucks sometimes, because no one really empathizes up. But that's just life. So I shifted a lot of my coping mechanisms and stress relievers. I invested in external friendships, routine, gym, eating more healthy - these kinds of things so that I could be the best-performing CEO in my job, and see myself less as the founder who bears all the ultimate responsibility.

Because when you start a business, you do feel a huge sense of responsibility to make it successful. You've convinced all these people to join, leave their high-paying jobs, take a risk on you. You've convinced customers, investors, friends and family that this risk is worth it. So you feel this huge responsibility to actually make good on that and prove to everybody that you were right all along.

But then you realize that actually, it's not all on you. Once you start to hire people, build the executive team, get the right people in the door, you can actually pass a lot of that responsibility to other people. And then it becomes more of a team sport.

A wise man full of so much wisdom. Thanks for sharing all of it with us, Benjamin.

Further study on Dovetail… 🕳️🐇

• The story and PLG breakdown of Australia’s next big tech company

• Five ways we reinforce our product-led growth model at Dovetail

• How to choose the right research methods for your discovery process

• Pulling back the curtain on Dovetail magic

• Dovetail for product managers

Hopefully, it’s clear how valuable Dovetail is. If you want to try it out for free and create a single source of truth for your customer knowledge—give it a go here.

Before we all say goodbye, three quick things. 🙏

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Hi, friends 👋

Today’s piece is shorter than usual, and a totally new style. Compared to the usual 10,000 word write up, this is a Q&A style letter between me and probably the highest profile guest I’ve had here so far—Shopify’s Chief Revenue Officer, Bobby Morrison.

Shopify needs no introduction. But if you’re not familiar with Bobby, here’s his incredible resume: Before joining Shopify in August 2022, Bobby has had leadership runs at Intuit, Microsoft, and Verizon. He’s also advised several companies, and one of my first questions was what main lessons he’s learnt across each company that have shaped him as a leader.

The style of this piece is as follows: I asked a question, Bobby sent me an answer, and I’ve also then added where relevant, my own comment per response, giving you some additional analysis.

It’s not the usual deep dive, because I’ve already written that here. If you haven’t read that piece I’d suggest starting there, although you don’t have to.

This is a follow up, because when I wrote about Shopify back then, they were not playing the enterprise game. Shopify in 2022 was deeply positioned as the #1 platform for entrepreneurship. In Nov ‘22, they were valued at $42.48 billion.

But, at breakneck speed—and also very much coinciding with Bobby’s arrival at Shopify—they’ve quickly launched themselves into the enterprise category and are already leading this section of the market.

Today, 18 months later, their market cap is $73.48 billion.

Yes, Shopify has deep resources to invest in expansion and aggressive go-to-markets to help win a pool of customers faster than most of us could ever dream of. But resources alone are not it—there are of course companies who’ve had war chests larger than some countries GDPs who have failed to get into new markets.

Shopify have executed this push to building the enterprise commerce operating system off so well, because they’ve focused on first-principles:

• Spot the macro trend

• Craft your insight

• Lean into your unique advantages

• Develop a strategy that stays true to the core mission

• Clear the path of side quests, say no, and focus on main quest only

• Find where the main value is, and amplify it

• Find where the main friction is, and remove it

For this reason, there’s a lot to be learnt from this new phase of Shopify’s growth. A phase of growth that Bobby has his fingerprints all over.

This is also a timely piece given Shopify’s recent Q1 earnings call, touting great performance with $1.9B in revenue this last quarter (up 23% YoY).

Let’s get to it.

*This post is in paid partnership with Shopify

How Shopify is winning enterprise, with Bobby Morrison 

1. To open up the floor, is there any guiding wisdom or business philosophy that’s really stuck with you over your career?

I embrace the concept of being “antifragile.”

It’s not just about overcoming challenges, but learning and improving because of them. I really value work environments that challenge the status quo and believe in continuous learning and improvement. 

My comment:

I first learnt about the concept of "antifragility" when I read Nassim Nicholas Taleb’s book during lockdown.

Unlike fragile items (i.e a glass) which break under stress, or robust items (i.e a rock) which remain unchanged, antifragile systems actually improve and become stronger when exposed to volatility, randomness, and stressors.

The best example is us—humans. When we lift weights, the stress causes micro-tears in our muscle fibers. But with recovery, the body repairs these micro-tears and we grow stronger and more resilient.

In practice, there’s a few ways we can apply this at our own companies.

1. Seek out the challenge: Instead of avoiding what’s difficult and doing the comfy stuff, we should view obstacles as opportunities to learn, adapt, and improve our skill and product. For example, think about if there’s a conflict on the team that could be resolved, or maybe a hard question your team is skirting around—like a competitive threat or the risks of AI. If you position anything hard in your mind as a way to become more antifragile, you’ll find a new motivation and zest to do the difficult stuff.

2. Take big bets and prioritize experiments: You just have to try new ideas. Some of them will be low hanging fruit, but some may be radical that could bring step changes to growth vs incremental optimizations. You need to create a culture of testing both. What’s the saying? You have to fuck around to find out.

3. Build for redundancy and optionality: A key part of antifragility, which is super evident in Shopify’s business, is creating systems and strategies that allow a company to benefit from the unexpected. In short, that means building multiple revenue streams, expanding into new diverse customer bases (like Shopify with enterprise), and baking in flexible business models that can easily adapt to changing circumstances. If you found out a pandemic was going to hit next month, what would you do right now to protect your business?

4. Embrace small-scale stressors: One thing you can do (which relates to seeking out the challenge) is to intentionally expose your business to small-scale stressors. This is basically controlled risk-taking to build for resilience and adaptability. I have not done all these things personally, but in thinking about it now, practically this could be:

   1. Controlled hackathons, where you give your team experimental projects within a short timeframe. This exposes folks to time pressure and resource constraints, and pushes them to think creatively.

   2. Rotating roles and responsibilities, where periodically you have people get involved in other areas of the business, thus exposing them to new operational context, challenges, and working styles.

   3. Simulating outages or failures, which helps the team prepare for real-life incidents. It also points out weaknesses in your systems, and helps to develop contingency plans.

   4. Entering new markets or niches, which helps test your company’s ability to adapt to different customer needs and market conditions.

Basically, Bobby’s guiding philosophy on business is to create a company that not only survives, but thrives in the face of uncertainty, challenges, and the inevitable unexpected punch to the face.

2. Related, do you have any standout lessons that you’ve learned from your time at huge companies like Shopify, Intuit, Microsoft, and Verizon?

From my time at Shopify: 

• Shopify is the first founder-led company I’ve been a part of, and there is a clarity of mission that comes from our CEO and founder Tobi that is unmatched. The power of viewing everything as a product has a tremendous impact. We view marketing/ops/support/commercial as a product.

• Parkinson’s law, the concept that the work expands to fill the time allocated for its completion. At Shopify, we apply that to bureaucracy–by giving it less volume, we allow more room for impactful work.

• Unorthodoxy is where alpha is created.

• The impact of saying “yes” to one thing is “no” to every other thing.

• The power of “deletion” and building back better. 

From my time at Intuit:

• The value of leading indicators, real customer obsession, and how to regain “fresh eyes” on the business. 

From my time at Microsoft:

• The power and scale of a global partner ecosystem; growth mindset; and how to integrate, as well as the importance of commercial and product feedback loops (connective tissue). 

From my time at Verizon:

• What relentless execution really looks like, the power and outsized influence of great leadership, the importance of diving into the data as an external face of the business, and deep understanding of the “Rubik’s cube” called the P&L.  

My comment:

Every experience we’ve had has taught us something big, and usually, that shapes the story arc of our careers.

But, we very often don’t actually sit down to think about it. We put in real time and work to do some job, but then move onto the next gig without putting in just a fraction of that time to figure out how that work changed our view on anything, or brought as some new perspective.

So my comment here is more of a challenge to you—find some time to think about just one thing you’ve learnt from each work experience you’ve had. And similar to Bobby’s examples above, avoid hard skill stuff like “I learnt SQL”, and think more about larger life/professional/perspective/philosophical takeaways.

For instance, one thing I learnt while being a bartender (outside of making some mean cocktails), is a teams energy, quality of craft, and speed of work is actually a lot higher when there is a lot going on. When little is demanded of you, you slow down to let your work fill the space, and with that slow down comes low energy.

Busy + direction = quality & velocity

3. Shifting gears to Shopify, what’s the difference between Shopify Core and Shopify Enterprise? How much of this initiative is dedicated new product, vs new marketing/positioning?

Our goal is to give enterprises the tools to build with the highest velocity across full stack, composable or headless with a lower total cost of ownership (TCO) to drive revenue. The larger a business, the more opportunities there are to leverage Shopify’s tools and scale. Enterprises get access to their own dedicated version of the Shopify platform that powers over 10% of U.S. ecommerce. We continue to build enterprise-specific value, such as controlled releases, unlimited locations, enterprise level support and SLAs. 

My comment:

So, yes, there’s often net-new product that needs to be built to move up market. The needs of enterprises, while often overlapping in many ways with SMBs, are different.

By building a separate version of the Shopify platform just for these types of businesses, Shopify still gets to reuse key commerce components they’ve built over the past 16 years, but can bring extra power to a smaller group of users without adding complexity to the core interface for the bulk of their other customers.

A nice play.

In addition to that, I love this concept Bobby brings up of Total Cost of Ownership (TCO).

TCO is a financial estimate that helps determine the direct and indirect costs of a product or system over its entire lifecycle. It goes beyond the initial purchase price and considers all the expenses associated with owning, operating, and maintaining a piece of software.

For a big company, the costs beyond the direct subscription or annual contract are often substantial. Which means for founders looking to move their product up-market to enterprise customers, understanding and leveraging the concept of TCO can be crucial in winning deals.

Here's 4 ways how you can use it:

1. Highlight your product’s long-term cost savings: Enterprise customers are often more concerned with the long-term costs of a product rather than just the upfront price. By demonstrating how your product can reduce costs over time through factors like increased efficiency, lower maintenance costs, or reduced need for additional hardware or software, you can make a pretty strong case for your product's value. The idea is to map out how your TCO over the next 5 to 10 years beats their current TCO, even if there’s a big upfront cost or effort. That’s how you can convince people to make a big switch.

2. Emphasize scalability and flexibility: Enterprise customers heavily index on choosing vendors where they see staying power. In other words, they don’t want to see a future where they outgrow your product and have to deal with changing tools. So, show how your product can easily scale up or down based on demand, and is adaptive with their growing needs.

3. Focus on reliability and support: Any downtime or system failures impacts productivity, and than can be incredibly costly to enterprises. This means you need to highlight that your product's reliability and level of support is best-in-class. This can include offering dedicated account managers, 24/7 tech support, or service level agreements (SLAs) that guarantee uptime and quick issue resolution.

4. Provide TCO calculators, data, and case studies: Shopify is a great example of this. Their enterprise page is all about TCO, and they have the content, research, and tools to prove theirs is excellent. They know TCO matters, so they commissioned independent research to bring objective data to customers around where they can get the most bang for their buck. They also built a free TCO calculator, and have several case studies that demonstrate the long-term cost savings and ROI of their platform compared to alternatives. All these things can help your prospective enterprise customers understand the full financial impact of choosing your product and justify the investment to their bosses.

Basically, TCO is your friend in winning enterprise contracts and moving up market. Once you know all the things people care about in their buying decision, you can get ahead of it by addressing the TCO concerns. Here’s an awesome component Shopify use on their landing page for enterprise.

4. Why now? What was the discussion that led to Shopify for enterprises after 16 years? What tailwinds and behavioral/tech/cultural/societal/macro shifts contributed to this?

Our mission is to make commerce better for everyone. And when we say everyone, we mean everyone. We recognize that this new era of commerce is challenging based on market conditions, which are further amplified when a business’ commerce platform is inflexible and expensive. This market demands profitable growth from enterprises, and we see ourselves as a partner to enterprises on that journey. 

In a recent survey we conducted with IDC, we learned that two-thirds of enterprise customers were looking to change their commerce platform in the next three years, prioritizing quick implementation and a cost-effective solution in choosing their new platform. We pride ourselves on speed to market and agility when it comes to moving businesses to Shopify. 

Building a 100-year company requires constant innovation, and our investment in enterprise is another logical step in our journey to be the full commerce operating system for businesses of all sizes.

My comment:

There’s always some wave in the market that you want to catch. Timing is everything, even for a massive company.

And for Shopify, their timing was a mindset shift about profitability in a challenging market. Things shifted from crazy hiring sprees and big budgets to more survivalist and lean thinking.

This was Shopify’s wedge to get slow moving enterprises to make a big change, because by knowing what was being spoken about at the table (saving money), they made their cost saving (presented as TCO) a flagpole for their enterprise messaging.

If you’re thinking about launching a product or entering a new market, what’s something the buyers (and users if you’re doing PLG) in that community are speaking a lot about right now? Be an internet sleuth on Twitter and Reddit, track what they’re talking and complaining about. Follow the memes. Read the stuff they’re reading.

You want to get into their mindset and come up with a compelling why now for why they’d consider buying your product.

5. What is the number one thing you’ve come to learn that enterprise customers care about? Is there any element that if you get right and address upfront, you can completely streamline a sales process?  

Everyone wants to grow in a really challenging market, and we help them do that in two ways: infrastructure and speed to market. Our powerful, reliable infrastructure and flexible products make the total cost of ownership very appealing. An independent study recently validated Shopify’s total cost of ownership is up to 36% better than competitors. 

Second, our core value proposition of innovation, scale and ease of launch. Enterprise businesses are initially drawn in by the low TCO, but there’s so much more to Shopify. We take what's complex and make it simple - absorbing, not offloading complexity.  We innovate faster than anyone - giving our customers the competitive edge they deserve. And we’re all in on Unified Commerce, which ensures a connected and consistent experience across all touchpoints. Not to mention our ecosystem of 8,000 apps on the Shopify App Store to solve for their changing business needs. 

My comment:

This stood out to me: absorb, don’t offload complexity. 

Basically, just make your customers’ lives much easier than they even expect you to.

Similar idea to Brian Chesky’s famous 11 star experience framework. My advice, give an honest assessment of how many stars your product experience has right now in terms of delight and absorbing work for your users, and then think about what adding just 1 extra star could look like.

6. I heard you say that the logistics business which you recently sold to Flexport was a distraction. You said “No side quests, stay main quest”. And for Shopify, that main quest is commerce. Not CRM, not ERP, not marketing services. But commerce is a massive term, there’s D2C ecom, B2B, retail. On the enterprise commerce side, was there a GTM focus, and if so, how was that determined?

Our go-to-market strategy for enterprise is unified commerce – DTC, B2B and retail. We want enterprises to be able to centralize reporting and visibility in one place for both their physical retail stores, DTC channels and B2B. That makes unified commerce a natural GTM focus for us.

My comment:

We generally think about picking a small niche when entering a new market and then ramping up from there, but sometimes, we have to do the inverse.

We have to go big from the get go.

Why? Because a narrow focus can lead to missed opportunities and steeper competition.

Usually, the move is for startups to create a super narrow focus for their product. It’s always “How can you be more niche?”, “Get more specific!”, and “Be careful broadening your scope”.

But when you think about the problems your customers have, they often span a lot of different business systems or point solutions.

In fact, some of the biggest problems, and therefore the problems that potentially could give rise to the most valuable companies tend to be things that span a lot of different point solution products within a business. And therefore, only building one point solution product can't really address them.

Plus, by focusing on Unified Commerce with point solutions for all of these areas (B2B, retail, online, POS, etc), Shopify is really betting on a suite of products, with integration as a product.

Meaning, the types and the depth of integration you can have when you're building a set of related products together in-house is so much more powerful than what you can do through a set of APIs with other vendors.

There are usually a set of shared components across products (FYI Shopify is literally built on components), where you can identify certain bits of functionality or certain parts of the product that end up being reused. This is not just great for efficiencies, but also means you can afford to go much deeper and invest much more heavily on those critical pieces that are shared across these different products.

So, go forth and think bigger. But do so in a way that is 100% aligned with your long-term mission.

7. Having a great hook and pitch—which you do—is obviously key to acquisition. But enterprises often get caught up in the status quo. And the bigger the company, the harder it is for them to migrate from an A to B solution. How is Shopify thinking about removing friction, and in terms of onboarding, how does Shopify operationalize implementations with big customers to ensure these setup projects don’t go over budget or timelines?

We take a truly bespoke approach to facilitating the transition to Shopify for enterprise customers because ideally, Shopify is the last replatform enterprises ever need to make. Our enterprise-level offering meets businesses where they are. We know that replatforming is a massive change, so we offer extensive customization options and integrations that allow enterprises to tailor their sites to their customers and integrate existing back-end systems seamlessly using APIs. This flexibility can significantly reduce the hurdles associated with migration.

For enterprise clients, we offer dedicated account managers and access to a consultation team to help aid in this transition. These experts help execute migration with minimal disruption to the business.

We also place a big emphasis on detailed planning and scoping before official onboarding even kicks off. We work closely with our customers to understand their specific needs, goals, and any potential challenges. 

From here, we leverage a robust toolset and framework that's specifically designed for large-scale implementations. These tools help automate and streamline parts of the setup, reducing manual errors and speeding up project timelines. 

We also employ a phased approach to implementation, which helps massive projects feel more manageable. Instead of going live with everything all at once, the platform and its functionalities might be rolled out in stages. This helps catch and address issues when they’re still small and manageable.

My comment:

Enterprises require a lot of handholding beyond sales. And if you want them to find value so you can retain their business and upsell them in the future, it’s super important to think about touch-based enterprise onboarding almost as a product in its own right.

One bit of advice here is to create an internal knowledge-sharing repo where team members can share their experiences, lessons learned, and new ideas for improving the implementation process. The idea is to iterate on your process, find the bottlenecks, and have a smooth transition over from sales to customer success.

8. You started as a challenger in the space. But within just 2 years, you’ve been dubbed by Gartner a Leader in the Magic Quadrant. That’s just a true demonstration of operational and strategic excellence. When you were charting the path to get there though, what was your strategy kernel? Were there specific product, marketing, and partnership requirements you knew you needed to nail to win the enterprise market?

One of the observations in August of 2022 was that we had two key areas to prioritize before we entered the enterprise space: certain product requirements and a series of partnerships that we needed, both commercial partnerships for how we enter the market and product partnerships to extend our platform and interoperability. 

We made some key investments, and at first, we were somewhat of a best kept secret for enterprise. Now, we’ve seen more retailers come over to Shopify that are billion dollar businesses, some of which are digital native and others that have been in operation for many years. 

My comment:

Once you know a) where you are now, and b) where you want to be, the next step is c) agreeing on what the right pillars of development are to get there.

Essentially your pillars are how you close the gap, and they ultimately guide what your roadmap should look like and what actions your entire team need to focus on.

9. What do you see as the biggest threat or risk to Shopify's enterprise business, and how are you building walls to protect against that?

We know it takes time and resources for enterprise businesses to replatform to Shopify, and for some companies, that is a barrier to entry. I’m confident if we continue to build incredible products, remove the pain of migration, and partner on solutions that allow businesses to scale now and in the future, enterprises around the world will continue to choose Shopify. 

My comment:

Sometimes the best way to build a moat around your business is to just focus on what you’re incredibly strong at, and thus what you can control.

Shopify isn’t directly concerned about competition or external threats—those are things outside of their locus of influence.

But what they can control is going deeper and wider on the problems that their market has. Building new features, improving existing ones, making their platform faster, doubling down on support, etc.

It’s a good lesson on not ignoring what’s happening around you, but also not spending too much time worrying about it. Most of the time, your biggest risk to losing customers is just failing to execute and deliver what they expect.

10. What areas is Shopify looking to invest in to a) lower the barriers to entrepreneurship, while b) raising the ceilings of scale, and for both sides of your ecosystem, c) help everyone do more with less.

We're supremely focused on making significant strides in B2B, offline, and international. 

B2B is a massive opportunity that will allow businesses on Shopify to scale and find new revenue streams. We’ve shipped more than four dozen B2B features since launching in 2022. In Q1 of 2024, B2B GMV (Gross Merchandise Volume) grew over 130%, and we expect that growth to continue. Others do, too: We received status as a Leader in The Forrester WaveTM: Commerce Solutions B2B, Q2 2024 in our first year of participation.

With many digitally native businesses moving to brick and mortar or pop-up in-person shopping moments, our POS product can now connect offline brands with over 150 million buyers on Shop, through our new email capture feature. 

We are laser-focused on building products and tools that cater to the unique needs and preferences of our international merchants. As we continue to diversify our product portfolio and extend our products into new countries, we will inevitably lower the barrier to entrepreneurship in these regions. 

11. What are one or two big lessons that founders in other markets can learn from Shopify's successful push into enterprise?

Shopify’s platform philosophy has guided our successful scaling to enterprise. We focus on three main principles: optionality, composability and innovation.

Shopify offers choice in how enterprise businesses use our capabilities to build their commerce stack, our systems are designed to talk to each other and our vast third party integrations, and we offer the most innovative commerce technology and the freedom for enterprises to focus on their own roadmaps and create value for their customers. 

My comment:

My takeaway here is flexibility.

We saw this last week when we looked at Attio—you want to build software that is largely unopinionated. Especially for enterprises who have very different workflows and needs from each other, building a platform that is flexible and doesn’t push customers into a corner seems to be incredibly important when moving up market.

Things are not always linear when it comes to workflows, and if you want staying power where your big customers don’t outgrow you, you need to think about optionality.

12. Tactically, how does Shopify make something complex and powerful behind the scenes while keeping it simple and intuitive on the surface? What lesson could be abstracted out for others looking to take inspiration from Shopify?

At Shopify, we remain focused on technical excellence. We spend a lot of time on our infrastructure, and this work often involves simplifying our systems. We must do this to keep innovating.

Our CEO and founder, Tobi Lütke, often says, “Not all fast software is great, but all great software is fast.” Some of the best returns on investment for Shopify have come from simplification. 

My comment:

Don’t let tech debt accrue for too long. As you grow into a scale up, you should consider stepping back and making a habit of spring cleaning your infrastructure and thinking about how to keep setting yourself up for future success.

I love that quote from Toby: Not all fast software is great, but all great software is fast.

13. What trends are you seeing in ecommerce? Where is the puck moving in the next few years?

We keep close to our merchants, so we’re seeing a number of trends emerging in commerce and retail as a whole. 

We see the incredible benefits AI will bring to our merchants and our business over the long term. We’re putting AI-powered products in the hands of more entrepreneurs, like our Semantic Search feature that yields more relevant results for shoppers and AI-enabled editing tools that generate studio-quality product images instantly.

We’re focused on helping entrepreneurs right now feel the impact of AI, and arming the next generation of businesses.

As in-store traffic has increased, we’re seeing digital native brands, including DTC ecommerce brands, moving into brick-and-mortar. Our POS products are designed to help these businesses expand into omnichannel retail.

My comment:

When it comes to playing where things are going vs where they are today, the number one thing you can do is to make sure you’re not building in a silo from your customers.

Startups are usually pretty good at being super close to users with things like interviews, community groups, etc. But larger orgs often start to rest on their laurels—they speak to customers less, focus on quantitative insights vs the qualitative, and build more from leadership’s ideas vs customer discovery.

If you want to be as close to where things are heading as possible, speak to more customers. Ask about what they’re worried about at work, what trends they’re keeping an eye on, what their customers are wanting, etc.

It’s not just learning about requirements, it’s learning about emerging needs that are not front of mind now, but may become so in a few years.

Adios!

And that’s it for our interview with Bobby Morrison!

To check out their new enterprise offering, hit the button below. You’re likely not a customer, but it’s interesting to just review their landing page and breakout of branding between regular Shopify, and Shopify for enterprise.

View Shopify For Enterprise

Otherwise, as always, thank you so much for reading! If you learned anything new today, you can sign up here for more issues.

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See you Friday!
— Jaryd ✌️

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Hi, friends 👋

I’ve loved Lego my whole life. As a kid, I’d spend hours following and building against the plans, then later breaking them down to customize and build my own version of some car, ship, or city.

The best was getting to combine and integrate Lego from one set (like Star Wars), with pieces from another (like Lego City), and creating some fictitious storyline that was just mine.

Being guided at first to build something you’d bought and wanted (i.e what you saw on the shelf), and then being given the confidence and flexibility to let your creativity come through and plug-and-play however you wanted in the pursuit of building something uniquely your own is, in my view, what still makes Lego the greatest “toy” ever.

Lego made a generation of builders.

And in recent years, us Lego-lovers have been blessed with a wave of software companies leaning into the same elements of flexibility, creative empowerment, integration potential, and playfulness.

These companies have brought disruptive plays to their market categories by focusing on giving users an unopinionated way of getting their jobs done.

These companies—like Notion, Airtable, and Linear—have won their markets, claimed billion dollar valuations, and created incredibly loyal fan bases for what I see as a simple yet undervalued reason: they let builders build.

Today, we’re talking about a fast-growing company that is playing highly competitive ball by building the Lego version of a CRM— an extremely powerful, flexible CRM for for founders, builders, and go-to-market teams of the next generation of companies.

Today, we’re going deep on Attio.

Attio is one of the few products I’ve come to love incredibly fast. Outside of having a remarkably powerful product that’s easy to use with a familiar and beautiful UI/UX, the reason I was so impressed so fast was because Attio has a ludicrously fast Time to Value as part of their onboarding and PLG motion.

We’ll go much deeper on this, but in short, while signing up I synced my work email and calendar. To my surprise and delight, a few seconds later when I landed inside the product, I saw a rich global view of all my relationships with all the people I’ve ever emailed.

I didn’t do a thing. I didn’t have to fill out a single field.

The platform succinctly drew a timeline of all the people and companies I’ve ever engaged with, and created profiles presented alongside intelligent insights based on hundreds of extra data points that were automatically enriched and filled out.

Within just 5 minutes of using Attio, I was playing around with:

1. Filtering my contacts based on attributes like connection strength, LinkedIn following size, estimated company review, and country (among many others)

2. Asking for pie chart reports on the job titles, industries, and the seniority of the people within my network

3. Using a done-for-you template to populate a sales Kanban board for How They Grow’s partnership deals

4. Creating Collections/Lists of people—like my contacts who are founders, investors, and marketers

This was literally just the tip of the iceberg. Attio had no business being so valuable so fast.

So, of course, I went deeper. And just like I did with my Lego, I pulled and plugged to make Attio my own.

It became super obvious that Attio, despite being a CRM, isn’t limited to sales or marketing. The platform’s modularity makes it a CRM that cuts across many verticals and use cases. Whether you run a high-growth PLG startup, a B2B marketplace, or run a modest little newsletter like mine, if you have a product that you’re bringing to market and your relationships with people and companies matter (when don’t they?)…then Attio will work for you.

The second thing that became apparent is that their secret sauce—which is very hard to pull off— is that Attio is simple when you need it to be, but advanced and powerful when that’s what you or your team need. Simply put, the power/complexity of Attio is fluid, yet the usability and intuitiveness is fixed.

This is all great and well, but let’s not forget the elephant—the humongous elephant—in the market. Salesforce is the CRM authority who reign supreme. Marc Benioff is a force to be reckoned with, with a $285B Death Star that has wiped out many CRM challengers who’ve ventured too near.

This makes for a great story, and at long last, a great Star Wars analogy I’ve had in my back pocket for a year and a half: The Rebel Alliance vs the Empire.

So, in today’s post, I bring you an analysis into Attio’s story, strategy, and PLG breakdown. To make it extra juicy, I was fortunate enough to sit down with Nicolas Sharp, their Rebel Leader CEO, who gave me an inside look at how Attio is building the nimble and ambitious Rebel Alliance and coming for the behemoth and heavily defended Salesforce Empire.

p.s If you’ve never seen Attio before, I’d suggest taking a look for context.

Part 1

The Beginning: A New Hope

I. The rise of an Empire

Why not have some fun with it 🤷 Click play below….

Lol. Here’s the slightly more detailed version :)

A Customer Relationship Management (CRM) is a system for managing all of your company's interactions with current and potential customers.

It’s the lifeblood of driving a sales pipeline and turning connections to cash.

In the late 1990s—while I was (true story) playing with my first Star Wars Lego set— the CRM industry was dominated by on-premises software that was expensive, complex, and time-consuming to implement and maintain.

It was a market ripe for disruption, and in 1999, Marc Benioff, Parker Harris, Dave Moellenhoff, and Frank Dominguez founded Salesforce with a vision to revolutionize the industry.

They saw an opportunity to create a cloud-based SaaS solution that was more accessible, affordable, and user-friendly, and in doing so, they not only set the stage for a new era in CRM, but they began a larger motion of software eating the world.

Salesforce's novel approach to software delivery eliminated the need for businesses to invest in expensive hardware and IT infrastructure, making it easier and more cost-effective for companies of all sizes to adopt CRM technology.

They did to the CRM category what AWS later did to server infrastructure. And what thousands of other SaaS companies have done in turn.

This leveled the playing field and made it possible for small businesses to compete with larger enterprises. Additionally, Salesforce's focus on customer success helped them build strong relationships with their users and establish a loyal customer base.

But Salesforce didn’t just build an Empire because they took the CRM to the cloud.

Salesforce’s growth and rise to ubiquity in the market was driven by its powerful data model, flexibility, and customization options.

This true Force was driven by harnessing custom objects.

The Custom Objects are strong with this one

Eventually, all companies need to tweak their processes to match the way they do business. Say you’re starting a sales motion, it’s fine to use an out-the-box solution to get going. Or even a simple spreadsheet will get the job done.

It’s a great starting point as it keeps teams out of unnecessary weeds early on when the goal is to just find a few people to buy your product.

But, as you sell more and your relationship graph of companies and people grow, you’ll mature your sales organization. You’ll get to a point where what got you from 0→1 won’t get you from 1→2.

Every team and business context is different, so it’s an eventuality that through finding success, teams will outgrow themselves and start to need more than the basic concepts. Stock-standard attributes like Name, Company, Email, etc—while still relevant—start to become secondary to unique identifiers per company and type of customer.

Salesforce recognized this. They knew that when teams were building their own on-site CRMs, customization was an innate feature because they spec’d out their own CRM needs.

So, in their chess move to build a cloud CRM for everyone, they brought the Custom Object to the CRM galaxy.

The name tells you what it does…it allows users to configure the objects they need alongside a CRM’s predefined concepts. The object can be anything you want.

I’m no mathematician, but: Custom Objects = Flexibility = A powerful data model

With that formula, Salesforce’s secret sauce was that they allowed their customers to bring their unique business process to the platform.

Salesforce remained unopinionated in its workflow.

And up until Attio, given the sheer complexity of it, there were really only two players that even attempted to support the custom object: Salesforce and Hubspot. But since Hubspot only have it in their enterprise plan (and added in many years later), in reality, only Salesforce truly delivers on the underlying promise of a flexible data model.

Many Salesforce instances will have hundreds of these objects ranging from Workspaces to PaymentGateways all in service of representing the full relationship between the business and their customers. This solution cleverly circumvents many of the problems that result from not having context by replacing them with deep configuration. 

— Alexander Christie, via Attio blog

Wielding this Force, Benioff has taken Salesforce to incredible heights.

Our story just starts here…

II. A crack in the Empire

But, in the immortalized words of Uncle Ben, “With great power comes great responsibility”.

And Salesforce’s responsibility was to manage complexity as they brought the market more power. As one ex-Salesforce customer said…

And here’s what another said:

If your customers can’t get to grips with the basic functionality of your system without expensive and extensive training seminars, how can they be expected to maximize the potential of the product?

Despite being a great piece of software—and one of the only ones that can model the unique sales process of a business— this has opened up Salesforce’s big weakness.

The hole in their Death Star is a result of their own success. And what’s more, Salesforce has built an economy around this complexity, meaning they don’t have a clear incentive to fix it.

The CRM complexity tax

In their ascent to $285B market cap, Salesforce has:

1. Layered in hidden costs, becoming an expensive item on any team’s budget.

2. Because Salesforce has achieved its flexibility by rejecting product context and replacing it with a highly configurable platform and an ecosystem of tools that connect into that platform, it requires specialized upfront configuration. This has made it increasingly laborious to get started with, and complicated to use.

3. Due to lots of features and lack of focus on design, it becomes increasingly difficult and less intuitive for people to use even once setup.

4. Become increasingly more expensive and time consuming to make any changes to the data model once it’s set up. Why? Because consultants often come in to create a Companies Salesforce instance, so once they’re done, regular users a) have no idea how to make changes, and b) are too scared to break things.

5. Become a time-consuming tool. Salespeople often spend more time feeding their CRM and updating data entries (often in multiple places) than their primary job function—selling.

6. Just become slow. Salesforce is old and running on a legacy architecture that just can’t keep up with the expectations users have for modern software. And, Salesforce is in a pinch because they have promised backwards compatibility which makes material performance/infrastructure changes difficult.

All in, Salesforce’s size has created rigidity, which makes adjusting the Death Star slow and has exposed a gap for a nippy X-Wing Fighter to get under the trenches.

With that, other challengers began to emerge.

III. Shortcomings of challenger rebellions

We know that the problem with Salesforce is complexity tax.

But, to understand where other challenger CRMs fall short, let’s talk for a brief moment about the First Airborne Division during WW2.

If you watched Apple’s Masters of The Air recently, you’d be reminded that the US was losing hundreds of B-17 Bombers and fighter jets to enemy fire and flack over Germany.

On analyzing returning planes, an interesting pattern was observed.

What do you see?

Probably the obvious, and exactly what the Allies did—most planes were being shot on the wingtips, central body, and elevators.

The solution to protect the planes? Just reinforce the wingtips, central body and elevators.

Before reading on, do you agree with that analysis?

Well, then a contrarian statistician named Abraham Wald came along and argued otherwise. He suggested that the engineers should reinforce the armor of the planes’ noses, engines, and mid-body. Essentially, all the parts of the plane where there were no bullet holes, and no reported damage.

Why?

Because in reality, the planes getting shot in those areas were being destroyed from the damage and never had a chance to make it back to be analyzed.

In other words, the original analysis was flawed as an interpretation was made under survivorship bias.

Now, why is that relevant to the competitive landscape of CRM?

Because if you look back at the 6 real user reported problems I listed with Salesforce, you’ll see a commonality: they all orient around a complexity and a usability problem.

That makes sense, because all the companies that have “survived” and did so with Salesforce had to make their data model work. So, their visible problems are a byproduct of all that tinkering.

And any founder interviewing Salesforce customers to understand what their CRM should do differently would gravitate to the obvious feedback—make the CRM easier to use.

The result is that most challenger CRMs aim to solve legacy CRM’ problems this way. They are typically cheaper, far more straightforward, and allow users to get started more quickly without the need for lengthy setups and Salesforce specialists. Some of these startups even target specific verticals to better serve niche markets—like this one for Dentists.

The problem is these startups, just like the Allies at first, are focusing on reenforcing the areas that, while still important to fortify, miss the broader picture.

They aim to resolve complexity issues by way of removing the flexibility, and giving users an opinionated platform with a more rigid data model.

Which is very problematic, because what they do is take away protection from the critical areas like the engine to bolster up the more withstanding wings.

They are an oversimplification of a more nuanced problem.

Thus, the shortcoming of most challengers to the Empire is a simplicity tax that renders a weaker data model. One that users will inevitably outgrow if they survive.

And just like a beautiful car but with horrendous miles per gallon—only a small subset of people will ever use it long term.

The real key to success here lies in the ability to deliver a powerful, scalable data model that meets the needs of businesses of all sizes while providing a seamless, intuitive user experience.

Attio’s founder Nick knew this, because before Attio, he too founded a challenger CRM for VCs and private equity investors to manage deal flow. He took the road of building narrow, saw the shortfalls, and changed course to focus on the forest, not the trees.

Fundstack had lots of happy customers. Revenue was growing fast. By all measures, it was going well, but we felt it wasn’t ambitious enough. No matter what you’re building as a startup, you work damn hard.

We basically had this moment of realization: if we're gonna put all of this work into something knowing that this isn't the best version of what it could be, what’s the point?

So me and Alex sat down in a cafe and thought: hypothetically, if we were to pivot and really build something that we think would ultimately be much better and more ambitious than this, what would it look like?

And then we drew out what then became Attio. We couldn't help but go for it.

— Nicolas Sharp

IV. Bringing balance to the CRM galaxy

As Star Wars taught us in 1977, every force has a weakness. There’s always a shadow side to every advantage and strength.

The formidable Death Star of Salesforce had a vulnerability that once spotted, created a wedge for attack. The same is true for the strengths of other CRM startups that came before Attio.

And that’s the first lesson I learnt from Nick Sharp.

A big incumbent in a market of course is a threat, but it’s also an opportunity. Nick and his team used Salesforce heavily when he was a VC, and when ideating what problem to solve, he spent a lot of time figuring out what:

1. What made Salesforce great (i.e what people liked)

2. What tradeoffs they had to make to create that greatness (i.e what people didn’t like)

3. And which of those tradeoffs would be incredibly difficulty for Salesforce to maneuver and cover up (i.e how they could counter position)

You can do that for any company, and by doing so, will find a startup opportunity.

And by doing that analysis on Salesforce, as well as the existing challenger CRMs, that’s how Attio saw how to bring balance to a massive market.

Attio’s plan of attack: The strategy to bring down The Empire

After speaking with Nick, studying the market, and using Attio myself, the following strategic components stood out to me. I’ve added a quick note on how you could more broadly apply their move to your own product.

♟️Their Move:

• The data model is the underlying essence of the CRM. Without an incredibly powerful one, no CRM can grow with their customers. So, they are building a best-in-class one.

🎯 Your Move:

• Identify the core loop of your product and go deep on it. Invest heavily in making it best-in-class, as it will be the foundation for your product's growth and success. No other feature matters until you have that waxed.

• Really make sure you do thorough discovery to understand your customers' current and future needs. That’s how you make sure your product's core can scale with their evolving requirements.

♟️Their Move:

• By being the engine behind other teams; PLG and sales-led strategies, and attaching their pricing to the value Attio brings those teams, Attio will always grow so long as their customers grow. The scalable data model means they can capture and retain that value they create indefinitely.

🎯 Your Move:

• Develop a deep understanding of your customers' key metrics and objectives, and then use that in your Pricing & Packaging to demonstrate how your product directly contributes to their success.

• Continuously monitor and communicate the value your product creates for customers, using data-driven insights to reinforce your product's importance in their growth journey. E.g, If someone wants to downgrade their plan, show them what a premium plan has helped them achieve and what they will lose.

♟️Their Move:

• Investing in customization and integrations will widen their serviceable market, as it makes Attio a horizontal CRM that works for any industry, any size and type of business, and most use cases.

🎯 Your Move:

• Develop a robust API and documentation that enables customers and third-party developers to build custom integrations and extensions, increasing your product's versatility. That’s how you become an ecosystem and solve a bigger surface area of problems.

♟️Their Move:

• Attio is focusing on a bottom-up play with a reverse-trial offering, targeting the real builders and operators, and using them to wedge into a larger org and invite more people. Compared to long sales cycles with decision makers, Attio is leveraging builders to build internal conviction.

🎯Your Move:

• Use a reverse trial—no credit card—to get users experiencing the full value of your product for a limited time. Suggest that they stick to a paid plan to keep certain features, but also allow them to downgrade to an unlimited freemium plan at the end. Just make sure to remind them what they’re about to lose.

• Delineate between individual vs team onboarding flows. A first time user vs a user joining a company workspace should have a different path. Read more about that here.

• Know when to suggest that individuals invite other people without being pushy. First prove your value as a single player tool, then hint at even more value with multiplayer.

♟️Their Move:

• They make it easy for power users to dive deep and build advanced things, but just as easy to hang around the surface of the product, get value, and not get overwhelmed by stuff that light users don’t need. When you need depth, it’s obvious. But it doesn’t sit there and confuse you before you’re ready.

🎯 Your Move:

• With onboarding—which extends beyond just sign up—context and timing matter so much for how you show users around your B2B SaaS. Don’t tell people what your product does, and don’t show them everything all at once. You want to be simple on the surface, advanced down below, and make it incredibly easy and progressive for users to oscillate between layers of functionality.

♟️The Move:

• Automatic enrichment is the default vs cumbersome manual data entry.

🎯 Your Move:

• Leverage AI, machine learning, and third-party data sources to automatically populate fields, suggest relevant information, and streamline workflows. This can kill your friction.

• Lean into the power of defaulting features to on. Focus on building things that most users will want enabled, and allow for a path to opt out.

♟️Their Move:

• Modern teams want multiplayer collaboration, and Attio is doubling down on team value by combining the graph networks of collective company emails. The moment several people from the same company sync their emails and calendars, the relationship graph for a company becomes 10x more interesting. Now all interactions across all company users join the CRM, vs a single person’s touch point history.

🎯 Your Move:

• Identify opportunities for collaboration and collective intelligence within your product, using the combined data and interactions of team members.

• Aggregate and analyze data across team members to surface valuable insights and recommendations that individual users might not have access to.

♟️Their Move:

• Build a brand that teams who use tools like Notion, Figma, Slack, etc can resonate with. Unusually for a startup, Attio did a full rebrand early on to appeal to their ICP of the builder archetype.

🎯 Your Move:

• Identify your ideal customer profile (ICP) and the other tools they frequently use, understanding their preferences, values, and aesthetics. This can help you create a brand identity that aligns with their expectations and resonates with the broader ecosystem of products they rely on.

• Continuously refine your brand based on customer feedback and market trends, ensuring it remains relevant and appealing to your target audience. This can be reflected in homepage redesigns, messaging audits, and fixing marketing debt.

With this series of strategic moves, I believe Attio’s growth will follow a trajectory similar to these companies (most whom I’ve covered) that have peeled away a segment of the market from their respective incumbents

• Gmail → Superhuman

• Mailchimp → beehiiv

• Chrome → Arc

• Wordpress → Webflow

• Photoshop → Figma
  

Give Attio a go

The Go-To-Market: Launching with Force

Attio followed a tactic that has worked well for companies like Figma, Airtable, OpenAI, and Notion.

They ignored traditional startup wisdom and didn’t publicly launch their product until it was largely fully formed.

Just like if The Rebel Forces had attacked The Empire too early, they’d have been crushed. They needed enough momentum, strategic insight, and firepower before scaling an assault.

So after deciding to focus on the broader CRM market vs a narrow solution, Nick shepherded Attio into a heads down build mode for 3 years. They collected emails via a waitlist, worked tightly and behind closed doors with a few ICP customers to refine their product, and made sure that for launch, they had built against first principles the CRM they knew the market needed.

They made sure to take no shortcuts and inherit no bad patterns developed in other CRMs.

Here’s the lesson: Don’t launch, onboard

Startups usually launch (and maybe re-launch) as soon as possible to quickly start iterating on a half-decent product.

Take Uber as an example. They were creating a new market, where the alternative is usually a terrible experience (getting a cab before Uber sucked). And since ride-sharing was a new space, there was a pressing need to be first.

When that’s the case, get out there, and as fast as you can. People won’t care if the product isn’t perfect. Anything you release is going to be worth it for some people, and that gives you a small advantage. When you have a network effect, like Uber, that small advantage is going to start compounding on itself.

But Attio wasn’t entering a new market where there is a land grab opportunity. CRM is a big space. They are a premium product competing against Salesforce, without an explicit network effect built into it. Therefore, the bar to launch was much higher.

That’s why they chose to take more time building, and do a gradual ramp up of users.

And from a similar point of view, the competitive products that were, and still are, on Nick’s radar are not the ones building CRMs.

He sees them as being too caught up in the past, trying to solve the problem that the legacy CRMs created without any real shot at competing on the data model or performance front.

Rather, he’s keeping an eye on products that may not be considered CRMs at all today but could become them in the near future as the new market paradigm evolves and becomes more widely understood.

These are the products that may be working on CRM-adjacent problems that could eventually see a bigger opportunity in CRM.

A beautiful insight for founders: look in unexpected places for competition. It will keep you watching where the puck is going, vs where it is or has been.

And after 3 years, without getting distracted by the competition, Attio launched in Q1 of 2023.

The approach to the Death Star was on.

Part 2

Attio’s PLG Breakdown: Understanding each layer of the Iceberg

The early innings of Attio’s customer acquisition was classic B2B GTM: founder-led sales.

Nick was tapping his personal network, scoring Reddit, Twitter, and community pages, and just focusing on Attio’s ICPs who were open to trying a new type of CRM.

This is really the only way to start B2B…I’ve never seen a startup find their first 1, 10, 100 customers in really any other reliable way.

This approach puts the founder in the driving seat to meet, build relationships, and learn from probably one of the most influential and direction setting cohorts of customers a company will have. Without directly interfacing with customers, you lose the feedback loop and ability to test if your product’s message is fitting the market, etc.

By doing founder-led sales, Attio got to a point of adding about 5-10 accounts per month—in the early days even winning Coca-Cola.

Aside: Curious how to transition out of founder-led sales? Here’s a great framework

In this early phase of acquisition, onboarding was white-glove. Everyone joining had Nick or an early team member making sure they understood what Attio did, how it was different, and crucially, manually migrating their data into Attio.

Nick told me this took days to get done, but was essential in figuring out how to actually operationalize that flow within the product.

Organic/word-of-mouth has always been a huge input of leads for Attio. In the beginning—while this sales and onboarding processes stuff was getting figured out—this demand was pushed towards a waiting list.

But, once they did figure that out and added a bottom-up, product-powered loop to get people signed up, paying, and expanding their accounts—growth just took off.

The PLG Iceberg recap

Kyle Poyar posed the question: Can PLG beat Salesforce?

Here’s my answer:

• “Beat” isn’t the right word. I think Attio can “beat” Salesforce in a similar way to how Figma is beating Adobe. Salesforce will always be bigger, but Attio can carve out an exceptionally valuable slice of the market for themselves.

• And that will happen if Attio can perfect all the layers of the PLG Iceberg.

In short, for the newer readers who haven’t read the Canva or Miro deep dive, the Product-led Growth Iceberg is a handy framework I developed to think about the varying layers of self-service growth.

Essentially the Iceberg represents a funnel, starting at the tip with the table-stakes of PLG. If you can’t get this right, nobody will even try your product so all the deeper, less-obvious, but more potent levels of PLG would never even matter.

As a company crushes one layer, their PLG motion progresses along incrementally harder phases toward the bottom of the Iceberg, which gets to the biggest challenge of all: can the product through operationalized acquisition loops naturally get one cohort of customers to bring in another?

All in, if you pull all of this off, you very likely have product-market-fit and a sustainable, low-cost, distribution system.

It’s the holy grail of product growth.

So let’s go through each of Attio’s layers and see what we can learn.

Layer 1: Core problem communication

Simply put, do people understand within a few seconds, and above the fold of your homepage, why your product will help them solve their Job-To-Be-Done.

PLG means your product is your #1 salesperson.

So, just like a salesperson reaching out over LinkedIn or email to get a prospect’s attention, it should not start with something dry and generic like “Hope you are well…”

Lead with value, be crystal clear, and the more you can personalize a leading message to someone (think dedicated landing pages for campaigns, personas, use cases, etc), the more of a shot you’ll have to get them to invest more time in discovery.

And that part is essential, because most people in B2B are not signing up without scrolling some more and poking around a few other pages before making a decision.

When I chatted with Nick about this, what really stood out to me was how he described the concept of “Why us” vs “Why one”.

“Why us”, vs “Why one”

When you’re selling to someone, you’re either:

• Explaining why someone needs any solution to a problem (why one).

  • Think about a category-defining product like the Apple Vision Pro. Apple needs to educate the market why they should fork out $3000+ to buy their headsets. What they’re pitching against is apathy to the problem.

• Explaining why someone needs your version of the solution (why us).

  • Think about the famous ScrubDaddy pitch on Shark Tank. Everybody knows they need to clean dishes and that a house needs a kitchen sponge. The pitch isn’t convincing people why people need a sponge, it’s that they need their sponge.

Over to Attio, the game in Layer 1 of the Iceberg is using product-marketing to tell people why they need Attio over another CRM.

Here’s how Nick put it:

CRM is a “why us” market rather than a “why one.” People know what a CRM is and know that they need one.

So our job is to answer the question convincingly as to how we’re different from other CRMs in the market.

A lot of that is done through brand and it's done through crafting a message, a look, and a feel that resonates with your target audience.

We knew early on that we're up against incumbents and we're trying to persuade people that we’re better than them. Brand plays an important role in that.

— Nicolas Sharp

That last point about brand is interesting, because usually investing in brand and comms starts to happen in B2B post Series A. But when you’re playing in a crowded market like CRM and differentiation is exceedingly important, building a challenger brand that holds its own like Attio has done is essential.

Let’s analyze their homepage for a second.

Some observations on how they’re putting the product’s value first.

• The hero copy plays on the word CRM by spelling our Customer relationship magic which is clever, witty, and hints at a subliminal message of what the product is. But while a word like magic is generally eye-rolling, in this case, it’s not misleading at all. During onboarding, you truly do get a magic moment. This is a statement that catches the eye and makes me want to read the text below to understand what is magical about Attio.

• The sub copy conveys Attio’s core value—a powerful data model that is flexible and configurable. In this sense, Attio is positioning its differentiation more towards other challenger CRMs vs Salesforce. That makes sense, because founders and early stage companies may be evaluating these folks more vs the enterprise-centric Salesforce.

  • But, just playing around, one version I’d be testing is to hit a note like this: As powerful and flexible as Salesforce, but infinitely more intuitive and fast for the modern builder. No hidden costs.

    • This calls out the competition, creating an instant anchor in people’s mind

    • It leads with why people like Salesforce, and why people don’t like challengers

    • It communicates how Attio solves the problems people have with Salesforce

    • It also mentions the “who this is for”, all in one sentence

• Attio are using the “show don’t tell principle” here by embedding a catchy but informative product video on the homepage. This is something I see tools like Slack and Atlassian are using too. It gives people a tease of the promised land behind the signup wall.

Once people are a little hooked with this leading attention-grabber, they may scroll to get some more information.

Here’s what they see:

The copy emphasizes:

• Notion-like value, emphasizing why builders may want to pick Attio

• Ease of getting started with templates

• Intuitive UI, a big differentiator to Salesforce

• Custom Objects, a big differentiator to challenger CRMs

• Workspace reporting and visualization

The thread in all their messages is feature<>value. This tells you what outcome you get, and practically, how Attio will help you get it.

This makes sure the copy isn’t vague, yet still value driven.

Never forget social proof

In the world of B2B, an essential point to understand when selling software—whether via bottoms-up or top-down—is that people want to look smart in front of their bosses.

Your goal is to help them de-risk their decision and internal pitch.

If you’re an influencer in a buying decision, you’ll have a lot more juice convincing a CIO or CTO to put down the company credit card if you tell them other similar companies to you are using that same vendor.

That’s where social proof comes in.

Right at the top of the homepage, even above the hero copy, Attio links to a page dedicated to informing prospects about all the other companies getting value from Attio. That’s a great tactic you should steal.

There’s logos, there’s customer quotes, and there’s thoughtfully-crafted case studies, like this one: How Marker.io uses Attio to drive product-led growth.

That’s a great page that users of Attio can share internally to build conviction in company-wide adoption. It’s basically trying to replicate the modern day equivalent of “Nobody gets fired for buying IBM”.

Layer 2: Friction & Value discovery

Once people have been convinced “why Attio”, the next key to making PLG work is to make it as easy as possible for users to get started with the product. You want the product to deliver value ASAP.

It must be flexible, with a low learning curve. If it’s too complicated, users will look elsewhere.

But at the same time, the rope to balance is:

• Fast and easy to get setup. AKA, as little friction as possible

• Healthy and necessary friction

The healthy and necessary friction is often overlooked by folks as they just try to open the floodgates as much as they can to get those acquisition numbers up.

But you need it. It weeds out poor quality users (e.g people who don’t really need your product, or will never pay you) and it also makes sure that the high-quality users coming in get to value.

Because on that last point, friction up front could well make it 10X faster to get to value post-signup.

Let’s take a look at Attio’s onboarding path from homepage to product dashboard, and we’ll see that in practice.

Screen 1: Picking the right hard requirement to act as a filter

What works well:

• Single-sign on makes one-click email and password entry super easy. If you don’t have this, definitely consider adding it in. It’s a UX pattern people expect.

• The page reminds people why Attio is different, nudging them to finish step 1.

• Attio requires you to sign up with a work email, including via Google Auth. This positions Attio as a business-grade product. And while it may seem like risky friction for anyone who just wants to see what Attio is about, this is an incredibly strategic requirement that benefits the user.

  • Using a work email, which they inform you about if trying to input a personal email, brings you a relationship graph of all the people you’ve interacted with professionally. That’s the value of Attio, so it’s a friction point that will a) weed out non-serious people, and b) make sure serious people have a short Time To Value.

Screen 2: Information for collaboration

I get why this step is here for a team-based workspace tool, but I’m not sure how necessary this step is. I’d probably do away with it for two reasons:

1. It doesn’t contribute to the user getting onboarded and finding value

2. It doesn’t capture any key information to filter qualified/unqualified people

If a user is using Attio in single player, this doesn’t matter much. One suggestion here would be to lose this step for individual user sign up, and push it into the team member onboarding and invitation flow.

i.e If you are working with others, add some profile info to make collaboration effective.

Every additional screen in onboarding brings drop off, so really always focus on the absolute essentials.

Screen 3: Where the magic starts to happen

This is arguably the most important action a user will take during onboarding. Nick told me there is a huge correlation here between users that sync their emails/calendars and retention.

What works well:

• It’s clear why you should connect your accounts.

• They use a smart default by choosing the option that is most valuable. This eliminates the guesswork and any thinking.

• They have simple 1-click buttons to make this connection happen.

• They use visuals to show you the power of syncing—like automatic enrichment from dozens of sources.

• They still give users the option to continue without a sync, giving an offramp to folks. The reason for this is they still allow you to sync within the product.

• They get ahead of peoples’ concern when it comes to sharing account data, and remind people how important privacy is and what Attio’s stance on data/privacy is.

Screen 4: Segmentation, forking, and workspace setup

This screen captures a users core use case. It’s a critical part of onboarding for anyone product that works for different personas and has variance in Jobs-To-Be-Done.

What works well:

• Only popular use cases are suggested, not all of them. This minimizes information overload for most people in the funnel.

• Related, as the second screenshot below shows, they use progressive information reveals to show sub-categories. Again, making sure to not overwhelm people with choice.

• It’s a nice touch that the visual on the right panel is adaptive to the choices a user makes. Small details like that compound to a user’s perspective of a product’s finesse.

• This segmentation is valuable for two big reasons:

  • It helps the user by generating them popular templates to get started with

  • It helps the user because onboarding email sequences will be focused on their reason for using Attio

  • It’s data that helps Attio drive a better sales pipeline

Screen 5: Kickstarting the product-led acquisition flow

The last part of onboarding is nudging users to start the bottoms-up flywheel and invite their team.

While you can use Attio in single player, it works best as a multiplayer tool. AKA, the more people on a team integrate, the sooner they experience the core value and the more “sticky” it becomes within a team, thus getting them hooked which increases their chances of upgrading.

What works well:

• They remind you why adding your team is important—it makes Attio more powerful for you

• It makes it easy to drop in emails and select permissions (with useful permission defaults)

What I’d suggest here is that they test adding a magic link. A simple copy and paste link that someone could drop in a Slack channel for example. The link would bake the invite parameters into the URL, and ideally take anyone clicking it to a page that is personalized, mentioning things like

• Who invited you, and from what company

• What use case that person is using Attio for

• Clear step to join the workspace and contribute to making the graph network even more powerful

Thinking of people’s email addresses is a hack.

Welcome (and goodbye): The reverse-trial and the downgrade path

Once inside the product, a user is greeted with a reverse trial.

The standout takeaway here is that they opt people into a reverse trial for Attio Pro with no credit card friction. AKA, unthrottled value. The bet they’re making is that by giving away everything for 2 weeks, people will build workflows, invite folks, and enjoy all the bells and whistles.

I love this lesson: provide value first, receive money later.

Then, after 14 days, they most likely (assuming they’ve used Attio) don’t want to lose that at the end of the trial. That’s tactic plays on two psychological principles:

• Loss aversion: a cognitive bias that describes why, for individuals, the pain of losing is psychologically twice as powerful as the pleasure of gaining.

• The endowment effect: a cognitive bias that causes people to value something they own more than something they don't own.

To see those effects in action, let’s jump ahead for a minute and look at these two brilliant screens a user sees at the 14 day mark when their trial ends.

Here’s what makes them so smart:

• It reminds people how many Pro features they’re using, and how many they will lose access to.

• It positions what they have as the middle ground of paid plans. If they want to downgrade, they can always go left and pay for a Plus plan.

• If a user selects to downgrade all the way to Free—which still has a lot of value for very small teams—then they highlight the very specifics of all the things that might break due to losing tool access. They also make users confirm they understand what they’re losing and how their workflows may change.

Tours and persistent onboarding

Once inside the product, Attio first points you around the UI with a demo.

Then, and this is always available, they have a sidebar that can be pulled up to guide you through onboarding.

Each step listed under “Getting started” makes Attio more valuable and becomes a strong indicator for retention and plan expansion.

This is almost always a good idea to have inside your software.

Templates: Eliminating the learning curve

After being shown around, one of the first things a user will do is create a List. This could be a list of all the VCs you know in San Fransisco, or literally any other collection of relationships you want to manage.

But knowing where to start could be tricky, and people want value fast. So, Attio has a wide selection of templates to get you going ASAP. From Kanban boards to spreadsheet-like list views, picking a boilerplate place to start means they de-risk people from getting lost in the sauce and not hitting that Aha moment.

This has worked wonders for platforms like Notion, Figma, Airtable, and the other no-code company Attio keeps.

Migration Assistance: Making switching easy

One of Attio’s biggest moats also happens to be the moat of their competitors.

If you’re setup in a CRM with existing workflows and tons of data, there’s big friction around switching CRMs.

Like being deeply embedded in the Apple ecosystem with your apps, phone, computer, watch, etc. Once you’re in, leaving is hard.

And because Attio is late to the CRM party, many of their target market customers are already using a CRM.

So, to combat that and eliminate switching friction, they make migrating from one CRM into Attio relatively simple.

To see and experience this stellar onboarding yourself, try go through their flow.

Layer 3: Repeatable Value

The real driver of sustainable PLG success is where users form a pattern of use around your core value action. This is what drives long term engagement and retention—without any habitual usage you (1) risk a leaky bucket and (2) minimize the product’s ability to qualify leads for the sales team.

Looking at Attio, there are a few main sources of repeatable value outside of their core loop that keeps people locked into Attio:

• Great feel and experience.

  • The UI/UX is state of the art. It’s slick, relatable, and for anyone who’s ever used Salesforce—just the ease of use is an ongoing point of value.

  • How a software feels—whether that’s tactileness, sound, animation, humor, flow— is key to any PLG adoption.

  • One of my personal favorites, and a growing UI pattern of the slicker products out there, is their expanding library of keyboard shortcuts. It just makes getting around so easy and skips the slowness of needing to move your hands between mouse and keyboard.

• Growing library of integrations.

  • By being able to connect Attio with your favorite apps, you can build more embedded workflows. Speaking of which…

• Advanced automations

  • Automations are workflows that get supercharged inside Attio. You don’t need them, but the more of them that you set up, the more effectively you can work and save time repeating rudimentary data entry and tasks.

• Infinite real-time reporting

  • Being able to slice up and segment all the data inside your CRM is super valuable. You can start simple with just a basic chart, or get more advanced and build out custom dashboards.

  • The more reports you generate (which are always kept up to date for you), the less likely you are to abandon Attio.

• Multiplayer mode

  • How much value you get from Attio is a function of how many connected company emails and calendars are synced. This is a big loop for ongoing, and new, value. Every interaction over email or scheduled event by a team member brings in new data and makes Attio a more important tool in a company’s stack.

• Growing template library

  • As Attio grows, they launch more and more templates that can streamline how easy it is to get your data visualized in different ways—often ways you wouldn’t have thought about without a template.

Here’s the takeaway: The best products have low floors and high ceilings

They move people along the product value curve really well. They do this by offering a super simple and quick path to value, while enabling users to discover and push the product further if they wanted to.

Layer 4: Monetization and Expansion

Typically, when you hear the word growth, it’s referring to user acquisition.

And while acquisition is a critical part of the growth flywheel, what many companies don’t realize is that monetization is the one of the most underutilized levers for growth in SaaS.

It’s the equivalent of personal income vs wealth.

Without income (acquisition), you can’t grow financially. But once you have it, your wealth is totally dependent on things like:

• where you invest your money (savings account vs the market)

• the fees you incur while investing (0.25% vs 1% will have a huge difference)

• how long you leave your investments alone for

The same is true for any PLG motion.

A study from Price Intelligently, a software engine for pricing, looked at more than 500 SaaS companies and analyzed what a one percent improvement in acquisition, retention, and monetization did to their bottom line. Their results were wild—the impact of improving monetization was 4x that of acquisition in building business value.

• Layer 1 and 2 = acquisition

• Layer 2 and 3 = engagement and retention

• Layer 4 = $$$

It’s worth really thinking about how to get this piece of the Iceberg right.

So, here’s the overarching question you need to nail: How do you create value and maintain trust with your customer while driving revenue?

In short:

• Know a) who you’re building for and segment users by b) what they value and c) what they are willing to pay. Those three elements create your positioning, and that’s the foundation of a monetization and pricing strategy. Once you have it — you can figure out your price point.

  • From here you can segment your pricing and do all sorts of interesting things, like upsell them in different ways and price based on different value points.

  • Crucially, what you charge needs to be based on perceived value. That’s the value the buyer sees based on their needs, not what you come up with at your desk. The better you match your price to perceived value, the less likely you are to leave money on the table.

  • If buyers don’t understand or don’t need the features you’re offering, then nothing else matters. For example, do your customers care about all of your 20 features, or do they really just care about 3 of them? The argument (which has been proven in pricing master Madhaven’s book) is that you can be a lot more successful if you focus your pricing on emphasizing just the 3. Perceived value > value.

• On Pricing & Packaging, you need to balance your Burgers and Shakes. Burgers represent the main reason people use your product. It’s your fundamental value metric, like storage for Dropbox, or seats for Attio. Shakes are premium features that boost the core value, but are not the value in-and-of themself. In Attio’s case, that could be unlimited reporting or deeper data enrichment—they are the things users need to upgrade to get.

  • Burgers and Shakes must work together to make one Happy Meal, and drive both conversion and expansion. In Attio’s case, users will get contextual upsells, like “Upgrade for more seats”, that push them to upgrade beyond the core value limit. These are huge monetization drivers because they are time-based, and catch a user when they have high intent, like inviting more teammates into their Attio workspace. Shakes typically require additional work around awareness and are dangled in front of users as a way to drive upgrades.

Attio strikes this balance perfectly, and it’s a key part of their land & expand strategy:

• No credit card upfront builds trust, as people see value before being charged

• They have 4 price plans, covering each ICP across the market spectrum (from solo entrepreneurs like me, to startups, to enterprise). What’s in each plan is based on what each of these buyer profiles need.

• They price their product against network-based value (more members connected = more workspace value = higher price).

• Attio has mapped the lifecycle of a target customer and looked at how to align value and usage over that lifecycle. This value pricing is attached to the size and growth of a company. If a sales org gets larger, they will expand their seats in Attio.

• There are zero banners or in-your-face modals to upgrade. Instead of being aggressive in pushing the upgrade, they rely purely on Burgers and Shakes.

• The Shakes are nested all through the product. Like this gentle paywall that appears when I hover over “Create Report” after using my 3 free ones. Great contextual timing.

This next point about pricing I found super interesting.

Attio is both more expensive, and more affordable

Through a combination of market research and speaking to users, Attio, as Nick said, “very unscientifically” chose an initial price.

For a product entering a crowded market, that approach to finding your price point makes sense because you have so many reference points.

Usually, in this case though, founders aim to be the bargain for money. In a commodity game, surely the lowest price wins? The idea is that by being the cheapest, you can land grab as many users as fast as possible. This makes sense if you’re building in a new market and there’s a clear first-mover advantage, or some kind of network or greenfield effect.

But, that’s definitely not the case with CRM, where the market is very established. And if you’re building a premium product like Attio, that’s where orienting around “When does it feel expensive but you'd still buy it anyway?” makes the most sense.

And this “unscientific” approach to “premium” has left Attio’s Pricing & Packaging in an interesting space:

• Their plans are more expensive than challenger CRMs like Folk or Pipedrive, but;

• Unlike these startups, Attio has a very generous freemium plan.

• And of course, to no surprise, their plans are substantially a) more affordable and b) easier to understand than Salesforce’s are

Do the math

The last point I want to bring up around startup pricing is back-of-the-napkin forecasting.

I said this to a colleague earlier today…forecasting is a fool’s errand.

And I really do think that any forecast that takes you more than an hour is a waste of time. You will be wrong.

But, quick and directional forecasts that are not shooting for precision can be worthwhile. One case is with your price.

For example, once you’ve picked a price, you can do a quick gut check on market size. This helps with:

• If you want to be venture-backed, as it gives you a high-level trajectory of how you grow into a $1B valuation (~$100M ARR). That’s $price x #customers.

• Figuring out what your enough is as a founder. Maybe your goal is to build a lifestyle business and do a couple hundred thousand a year in revenue. A quick forecast can help you figure out how long it will take to get there, and how feasible it is.

To point it out, those are both selfish reasons that don’t benefit your customer. Your price should not be rooted in what will make you rich or help you raise your next round. Your price must be value based for the user. Don’t tweak the price in favor of your needs/goals.

But, if using a true value-based price doesn’t get you a decent forecast, then you may well be working on the wrong idea.

Okay, into the deepest and final layer we go. 👇

Layer 6: Flywheels

If you can pull off a product-led acquisition (PLA) loop, thus getting one cohort of users to send more users to the top of your PLG funnel, you’ll be well on your way. 🌱

Why? Well, to answer a question with a question, what’s the best channel for acquiring customers?

Whichever helps you scale as cost-effectively as possible. And PLA means your users naturally invite other users while using your product—for free.

Now, the notion of PLA often gets people tripped up. Having a refer a friend button by itself is not PLA, because it’s not a natural loop—it’s an artificially incentivized channel that just happens to be accessible from your product. It’s less effective because:

• Most users don’t care about receiving a small cash reward—especially business users.

• Cash incentives attract users who are more likely to churn

• People get uncomfortable spamming their friends about products

True/natural PLA means you have a network effect, and that allows you to scale to your entire market without breaking the bank.

It’s the gold standard for growth for many reasons, but here’s a succinct one from Paul Graham:

Don't start a startup where you need to go through someone else to get users.

Generally, there are 4 ways you can integrate natural PLA into a product.

• Encourage users to invite other users. Not for any reward, but because it makes their experience more valuable.

• Turn your product into a billboard. When you send an email from your iPhone, or share a TikTok video, your email signature says “Sent from my iPhone” and your video is watermarked with the TikTok logo. Brilliant billboarding.

• Encourage users to make shareable content. When folks like me create content on platforms like Substack, we’re self-motivated to share it with others in order to build our audience.

• Trigger word of mouth. Either you create an incredible product experience and you delight users from entertainment (i.e shows on Netflix), or you delight them by eradicating a pain that they’re excited to spread the word.

Attio is doing all 4 of them. 👀

We’ll double click on each, but first, a different type of self-reinforcing loop.

The Chef Flywheel

Dogfooding is an overused term. Also, none of us eat dogfood.

I much prefer my term, The Chef Flywheel, because just like a chef testing his food, companies that rely on their own products to succeed will always build far superior products.

To explain…part of Attio’s land and expand play is identifying when customers are in a likely position to need sales intervention. For example:

• Seat count hitting a limit

• MRR climbing fast

• Downgrading from a plan

This is the essence of product-qualified leads. Attio uses all of these signals to figure out when to use a human to help get folks across the line and upgrade. But here’s the cool part…Attio uses their own product to do all of this.

With Attio’s Automations templates and Custom Objects—just like their own customers—Attio no longer has to manually monitor these PLG metrics. Like this one for monitoring if your customers increase their seat count.

Attio uses their own product to grow, even further marrying their own success to that of their customers. By tasting their product all the time, they build a better product.

You always want to be your own ideal customer. Your biggest food critic.

The multiplayer flywheel

Attio is intrinsically a team tool that gets better when more people you work with are inside. Nick made it very clear in our chat that the biggest signal for long-term retention is when someone invites someone else into their workspace.

It’s a core loop that drives their growth.

Billboarding

I think this picture covers it…

Each email sent using Attio, at least by users on lower price plans, markets Attio across all their customers’ unique networks.

Free advertising. Love it.

Shareable community-made content

This is a flywheel that Attio are not actually tapping into yet as far as I can tell, but they are in a prime position to leverage it, especially given their investment in community.

In short, Attio have two template libraries:

• Templates for Lists (i.e fundraising boards)

• Templates for workflow automations (i.e a churn monitor)

Right now these are all internally generated, which is of course limiting.

Attio’s audience is builders, so, why not let the builders share what they’ve built?

I’d certainly want to try out some workflow that someone like Lenny created.

I’m sure this is coming, and much like how community-generated templates have powered Notion and Figma, I think they can do the same thing for Attio.

Productizing and fueling word of mouth growth

Word of mouth can’t be stimulated. It will just happen when you make something great and get it in front of the people who need it.

But once you see it happening, you can lean in to support and facilitate it.

Here are 2 ways Attio are nurturing organic growth:

• Gamification. This is rare to see in B2B, but I’m all for it. To support their customers who are already spreading the word, Attio recently launched a referral program that rewards folks with points. One billed seat = one point, which can be redeemed for actually cool stuff.

  • Help me get a monitor please…Try Attio for Free :)
    

    

• Posting updates to Twitter and building in public. Another thing that helps accelerate WoM is posting about feature updates on Twitter frequently, as well as through email with customers. As Alex says, “We post even the smallest stuff because every update counts. The more you inform, the more ‘compound interest’ you create.”

And that, friends, is Attio’s PLG Iceberg. But where will it take them from here?

Part 3 […in video]

Future: Where Attio is going

The Rebel alliance is just getting started, here’s how I see the above growth motions propelling them forward, what I see them focusing on next, and my take on the bull and bear case.

Instead of writing it out, because there’s over 10,000 words you’ve already read, here’s a quick video.

Cheers! 🥂

Alrighty, that just about covers it for today!

Huge thank you to Nicolas, Alex, Alice, and Ilan for helping make this piece possible.

To show our appreciation, if you’re a founder, your relationships impact your revenue, and you think Attio is pretty neat, why not take Attio for a spin. I’ve been thoroughly enjoying it…if the above didn’t make it obvious :)

Otherwise, as always, thank you so much for reading! If you learned anything new today, you can sign up here for more issues. Also, consider sharing this post, or perhaps becoming a paying subscriber to support my work.

Subscribe now

Until next time.
— Jaryd ✌️

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Hi, friends 👋

I love products that work quietly in the background. The ones that consumers don’t even know exist, but that have a massive influence on their experience with, and the value they ultimately get from, another product.

Take the millions of Americans that drive a Ford…

I bet that less than 0.001% of them know that Ford uses Amplitude—the digital analytics platform—to understand how they’re using their car.

Drivers have no idea Amplitude is resting behind their experience, and helping product-builders at Ford make critical decisions around how best to serve them. The same is true for thousands of other products using Amplitude, and perhaps even the one you’re building?

After all, they do process (and help make sense of) over 1 trillion events a month. 🤯

Ultimately, businesses are built on how and why your customers interact with your product, which is why Amplitude is playing one of the most important, durable, and defensible games out there: The business of influential and actionable insight. Or, to boil it down to the brass tacks, Amplitude is in the business of making companies (a lot) more money.

How? By peeling away ambiguity and giving product managers, marketers, and operators everything they need to decipher how their customers are using their products.

And clearly they’re doing it right. Here’s some data on . How meta.

Another reason I’m super excited for today’s deep dive, is that I’m inside Amplitude every single day. I use them to track customer usage, understand our activation funnels, measure our KPIs, figure out where change needs to occur while identifying major drivers for that change, spot trends and issues, understand the impact of features on things like conversion and retention, run rapid experiments, inform roadmap decisions, and much more. Amplitude has helped my team and me so much, we’re even a featured customer under their new success story program. ✨

A great example of making your customers the hero of the story.

Amplitude is not just an essential tool in my own (and team’s) stack, and one powering an entire generation of world-class products you use, but they’re also a company that brings us a ton of lessons into how to build and grow a product.

So, let’s get to the meat and potatoes of it and unpack how Amplitude is winning, and of course, what you can learn from their playbook.

Here’s what to expect in today’s analysis

• How They Started: The First Data Point

  • When great isn’t good enough: Spotting and pivoting to the right idea by following the real pull

  • Why Amplitude? From Mad Men to Moneyball

  • A GTM (and PMF) lesson: Charge more, and charge sooner

• How They Grow: Up and To The Right

  • Amplitudes multi-faceted go-to-market

  • Buy low, sell high: A lesson on investing in your customers early

  • The data moat: A lesson on creating lock in

  • Compounded growth inflections: A lesson on building with breadth and depth

  • Content leadership: A lesson on SEO and brand-led growth

  • Amplitude AI: A lesson on doubling down on your unfair advantage

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How Amplitude Started: The First Data Point

Who was it that said perfect is the enemy of the good?

I can tell you who it wasn’t though…Spenser Skates, the co-founder/CEO of Amplitude.

To Spenser, if you’re going to commit a decade-plus of your life to building a company, you better pick the perfect idea to work on.

When great isn’t good enough: Spotting the right idea by following the real pull

Spenser believes if you want to be successful in the long term, you can’t settle on a good enough idea.

And for Spenser and one of his co-founders, Curtis Liu, that idea at first wasn’t Amplitude.

In fact, they worked on five or six different ideas that didn't turn out. The most promising was Sonalight, a voice-to-text app for Android, which they took to Y Combinator in 2012.

To many first-time founders, Sonalight would have looked like a hit. They had rallied ~500K downloads, had paying customers, and had the validation of being accepted to YC with the idea. Most would tinker with this idea…I mean, 500K downloads is nothing to scoff at.

Except, when looking at the numbers, Spenser noticed there was an engagement and retention problem, which was trickling down to challenges in monetization.

They saw this because the two MIT grads had built their own internal analytics tool to understand what was happening under the hood. Things like where people were getting stuck, what kept them coming back, what they liked to use, and what they didn’t. As Spenser recalls, “I remember looking at so many competitors – Google Analytics, Kissmetrics, Flurry, Localytics – none of them could answer these sorts of questions.”

So, just like how Slack found their billion dollar idea by looking at what they’d built internally to support their first gaming product (messaging), the insight for Amplitude came when Spenser and Curtis realized they were not the only founders at YC who had a problem with the state of analytics at the time.

And when they landscaped around with their peers, they quickly saw that the tool they’d made as a fun little hubristic engineering project on the side proved much more effective than anything the other YC startups were using.

“So many companies that we showed that data to were like, ‘Holy shit, you guys know this stuff? This is incredible. Can I get this?’ So we said, let’s build a company that serves the infrastructure behind that, which is what Amplitude ended up being.”

So, Sonalight got snuffed, and in death, paved the way for Amplitude. In 2014 along with an additional co-founder, Jeffrey Wang, Amplitude went live. Within 7 years, having raised $336 million from investors, the team took Amplitude public.

This brings us to lesson #1…

When looking for a B2B idea, pay close attention to any present pull.

Even if it’s not your core idea, if you identify something you’ve built that is showing signs of pull, and more pull than your actual idea, then consider pivoting fully to that.

Sonalight was a 95th percentile idea. Most ideas are terrible. It was pretty good, but it was not the bestest best. And it was like, we should probably go for a 99th percentile idea and go find that.

— Spenser

That’s such an interesting point, because sometimes an idea can be maneuvered from, say, the 95th to the 99th percentile. But building a super impactful business is hard enough, and what I’m picking up from Spenser here is that if you’re going to bet big on a company and spend years persevering, it’s worth playing around in the idea sandpit and being ruthless in how you prioritize them. Simply, a false start can set you on a many-years long race that may not even be worth “winning”.

As he says:

For a lot of teams, it’s a hard decision, because you’re talking about killing your momentum on something and restarting on something else, even when that might be the right decision. It’s hard to do because it’s existential, potentially. The entire thing can fall apart.

Of course, before making any big decisions like that, speak to lots of people to find evidence of a real pull (e.g. money, usage, strong emotion, cold inbound). Or, as Spenser suggests…

Speak to more people than you think you need to!

We did not talk to nearly enough people. We talked to 30 different companies within a month. I should have aimed higher, like 50 companies in a month. But we talked to 30 in a month before building anything at all just to see, ‘Hey, is this something potentially interesting?’

And out of that group, there were probably 10 folks that we identified that could potentially use this, and then five that had so much of a need they might pay money. Out of that group of 30, how many ended up being paid customers? A grand total of zero. We knew there was a need, but we made the mistake after that month of going straight to building, because we were like, ‘Well, instead of having all these speculative conversations, we actually want to have something to show people.’

— Spenser (Via Lenny’s Newsletter)

Takeaway 🛠️

Don’t get married to your ideas, especially in the early days. Just remember, it’s your time and your life being invested, so you must be your own biggest critic. You need to feel your own personal pull towards an idea. You can’t be lukewarm on what you’re potentially about to commit years building.

To set the stage a bit more before getting into their growth drivers, I want to briefly look at what made Amplitude a 99% percentile idea, and why there was such a pull from the market.

Why Amplitude? From Mad Men to Moneyball

Data, and an analytics company, certainly wasn’t new.

As touched on earlier, there was Google Analytics, Kissmetrics, Flurry, Localytics, and also others like Tableau.

But we also know those products weren’t serving that batch of YC startups well enough. So, what was the unique differentiator that made Amplitude so interesting?

Simple: accessible product data.

Product data, if you’re not familiar, is any data a user generates while using a product. When you open up Uber Eats for example, every action you take—from performing a search, tapping a restaurant, ordering, etc.—is captured and analyzed as product data.

This steady source of rich behavioral data around product usage means companies like Uber Eats can make better decisions more quickly.

But nobody was giving this to companies out of the box. And only the large tech-first companies were able to generate these types of high-leverage product insights—like Facebook’s classic “7 friends in 10 days” discovery—easily thanks to their custom tools.

This is because product data has three intrinsic properties, that back in the early 2010s, made it (1) accessible only to well-resourced companies, and (2) underserved by incumbent analytics tools:

• It’s very complex data: Every product has an unbounded number of actions that a user can take, and this complexity increases as a product scales. Meaning…

• There’s a huge volume of it: In 2012, data storage and processing costs made it prohibitive for most to capture virtually all user behavior. Also, the more data you have stored, the harder it is to make sense of.

• It’s also non-linear data: Unlike traditional marketing funnels where the goal is strictly increasing the conversion rate to the next step, users don’t take a linear journey through a digital product. It’s tough to sequence or orient around a bunch of behaviors and actions.

So, before Amplitude, the majority of companies had a patchwork of systems, stitching together things like web and marketing analytics, business intelligence tools, and sentiment tools to help understand the impact of their product investments. But, each of those had limitations…

Sure, some companies did have product event data stored in a warehouse, but because the data was so complex and large, it made it very hard to get quick insights and make assessments. The data wasn’t live, it was expensive to query and visualize, and there was no common visibility of it across teams.

For 99% of companies, finding actionable and real-time product-driven insights was a black box. Meaning, they didn’t always know if their strategic product decisions were the right ones.

In other words…

• Before Amplitude: Intuition-based decision making. AKA…

  • A “Mad Men” World, where folks gathered in a room to brainstorm based on nothing more than their gut and the qualitative of what people want.

• With Amplitude: Data-driven decision making. AKA…

  • A “Moneyball” World, where operators can look at the numbers, and the quantitative, to find long-tail insights, spot trends, and enable the right product bets.