How Dovetail Grows: 15 ideas you can borrow from their journey building the $1B insights hub

One of the most actionable and genuine interviews I've ever had, with founder/CEO Benjamin Humphrey

👋 Hey, I’m Jaryd! Here to help you build and grow your product with actionable deep dives into the growth drivers, strategy playbooks, and startup lessons from world-class companies. View all my previous analyses here.

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.

Placing customers at the heart of any organization is a huge challenge. While teams collect mountains of customer feedback (e.g. interviews, NPS surveys, sales calls, in-product feedback, app store reviews, usability testing), most are overwhelmed by analyzing it all efficiently. When insights emerge through arduous analysis, convincing stakeholders to take action remains a challenge. Moreover, stored insights are fragmented across cloud tools in disparate formats like structured survey responses, videos, or PDF presentations, making continuous learning difficult at best

— Benjamin Humphrey

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.

Dovetail just makes sense of every type of customer information source. It’s wild.

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.

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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’s transcription feature

“Dovetail instantly reduced my workload from 100 hours down to 10 to share out customer insights.”

— Eric Liu (Product Manager at Notion)

If you believe that a deep customer understanding is the main ingredient to building great products, and you want to drive action by aligning your team around real customer problems, then consider trying out Dovetail.

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.

You need to keep adding channels to keep the overall trend line going upwards

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.

🤿 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! 🤣

💡 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.

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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!

Peppa Pig…

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)

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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.

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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

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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.

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Before we all say goodbye, three quick things. 🙏

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