Tag: founder-led GTM

Start With the Story: Leadership Lessons from Drift’s David Cancel I Use to Elevate Teams

“Start with the story” isn’t a slogan for me—it’s a daily operating principle. As I guide product strategy and align go-to-market with product discovery, I’ve seen how a clear narrative unlocks focus, speeds decisions, and lifts execution. That’s why David Cancel’s perspective resonates so strongly: when you build from the story, you build momentum.

David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. That combination of product, engineering, and executive leadership creates the kind of pattern recognition I rely on when coaching PMs and shaping product management leadership practices across teams.

In my experience, the fastest way to align product, marketing, and sales is to anchor everyone in the same narrative. David’s framing around storytelling at Drift, a conversational marketing and sales platform, crystallizes this. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. I’ve adopted a similar approach—story-first onboarding for product creators and PMs, so every spec, roadmap, and customer interaction reinforces the same promise and positioning.

The leadership muscle here isn’t just crafting a compelling story—it’s keeping altitude discipline. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. I use these same moves: inversion to pressure-test roadmaps and risks, weekly rituals to reinforce priorities, and async video to scale clear, human communication without meeting sprawl.

On my teams, inversion clarifies trade-offs: before we pursue a bet, we ask, “If this fails, what will have been the likely causes?” That simple prompt improves product discovery, sharpens founder-led GTM motions, and accelerates product-market fit lessons. When we meet, we start with a crisp narrative—who the customer is, what their struggle looks like, and why our solution is the inevitable next step. Outcomes replace output, and teams rally around impact.

I’ve also found that storytelling is a coachable skill, not an innate talent. We run lightweight workshops where PMs deconstruct great narratives (including screenplay structures) and rebuild their own. The effect is immediate: clearer problem statements, tighter product roadmapping and sprint planning, and better executive readouts that move decisions forward instead of sideways.

If you want to dive deeper into David’s perspective, you’ll find practical resources worth bookmarking. You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom.” For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.

To learn more about how Drift approaches storytelling, check out this article David wrote for Inc:

https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html

To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/

If you’re leading teams, think of story as a system: a shared language for product, marketing, and sales; a filter for priorities; and a mechanism for speed. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills. When we start with the story, we don’t just communicate better—we build better.

Inspired by this post on First Round.

October 22, 2025
Win-Win Partnerships: Stripe & Notion Lessons to Negotiate Smarter and Scale Faster

I’m always searching for practical, battle-tested strategies to build platform ecosystems and business development motions that actually move the needle. Cristina Cordova, Notion’s Head of Platform & Partnerships, brings exactly that kind of rigor. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.

After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. Her candor resonates with the realities I see leading product and platform work — the high-leverage wins, the inevitable trade-offs, and the importance of structured decision-making.

In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways. Hearing how she navigated both reaffirmed a core principle I hold: partner success starts with a clear mutual value narrative and disciplined execution across product, GTM, and ops.

She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart.

What stood out to me is how transferable these lessons are to product management leadership. The best partnership strategies are product strategies: prioritizing integrations that deepen product-market fit, sequencing launches to maximize learning, and aligning incentives so partners champion adoption, not just sign paper.

On negotiation, I’ve seen the same patterns Cristina highlights. Win-win deals come from clarity on your non-negotiables, crisp success metrics, and a shared plan for activation — not oversized concessions. I coach teams to pre-wire decisions, define BATNA early, and document a mutual success plan that ties product roadmapping and sprint planning directly to GTM milestones.

Hiring and org design matter just as much as the deals themselves. Great partnership talent blends product discovery instincts with zero to one B2B marketing chops and the discipline of outcomes vs output OKRs. Structure the BD and platform teams so ownership is unambiguous: who drives integration quality, who owns co-marketing, and who runs partner QBRs vs OKRs alignment across the business.

Whether you’re building your first platform integration, leveling up a partner-led GTM motion, or refining how product and BD collaborate, the tactics here can accelerate your path. The stories of how Stripe and Notion scaled offer a rare, practical lens you can apply immediately — from selecting the right lighthouse partners to operationalizing the learnings across your roadmap.

Inspired by this post on First Round.

October 22, 2025
Inside Upstart’s Unlikely Rise: Dave Girouard’s playbook for pivots, speed, and hiring

I recently listened to a deep dive with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google’s billion dollar cloud apps business. Hearing his operating cadence and decision frameworks through the lens of a public-company founder was a masterclass for anyone leading product and business strategy.
From a product management leadership perspective, what stood out was how the initial idea evolved into a durable business model. Dave opens up about the early business model pivot and what it took to execute it without fanfare — flying under the radar of Silicon Valley — while staying obsessively focused on product-market fit. His candor about why he “sucked at fundraising” and how his co-founders have stuck together for almost a decade offers rare, unvarnished lessons on founder psychology, trust, and execution.
I’ve seen how operating outside the spotlight can be a strategic advantage: fewer distractions, faster iteration cycles, and clearer signal on customer value. Pair that with disciplined go-to-market, and you can build momentum the market only recognizes later. Upstart’s path underscores the compounding effect of shipping speed, ruthless prioritization, and a willingness to refactor assumptions when the data demands a pivot.
I especially appreciated his “Are you Airbnb or Paypal?” test — it’s a crisp way to force clarity on whether a product depends on network effects or transactional trust, which in turn shapes your product discovery, risk controls, and compliance roadmap. His advice to look at your career in landscape mode resonates with how I coach emerging product leaders: zoom out, map the terrain, then choose the next hill deliberately rather than chasing the nearest shiny object.
Dave also shares three mental models he leans on to manage his psychology as a founder. As operators, we all need systems that keep us calm under asymmetric uncertainty — especially when a business model pivot or fundraising cycle compresses the signal-to-noise ratio. I’ve found that writing down pre-commitments, instrumenting leading indicators, and scheduling deliberate recovery are complementary to the frameworks he describes.
On operating cadence, his “management by exception” philosophy aligns with how high-leverage leadership teams run: push context, pull exceptions. The practical implications are clear — instrument what matters, set thresholds, and let autonomous teams own outcomes. It’s a blueprint for scaling without bureaucracy, especially when latency between decision and customer impact must be measured in days, not quarters.
The hiring lesson that hit home: for executive roles, lean on references, not interviews. In my experience, backchannel signals about how a leader performs in ambiguity and aligns a founder-led GTM are far more predictive than a polished interview loop. Combine that with structured trials or outcome-based charters, and you de-risk critical leadership hires while protecting culture.
There are also transferable insights from what he learned from Google and how he runs his leadership team — tight feedback loops, crisp operating documents, and an insistence on speed as a habit. For AI-powered lending and beyond, the pattern is the same: clarify the decision, collapse the cycle time, and let empirical results, not narrative gravity, determine what scales.
If you’re building in fintech or any category where trust, risk, and regulation intersect, this conversation is worth studying. It’s a reminder that unconventional trajectories can still compound into category-defining companies — and that the right mental models, operating mechanisms, and hiring heuristics turn volatility into a strategic advantage.

Inspired by this post on First Round.

October 22, 2025
Twilio’s CEO on Peaks, Valleys, and C-Suite Truths: Hard-Won Lessons for Product Leaders

When I study enduring product companies, I look for the inflection points that shaped them. In revisiting the journey of Jeff Lawson, co-founder and CEO of Twilio, I was struck by his longevity and resilience — he’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016. From my product leadership lens, the arc of Twilio’s growth offers a playbook packed with hard-earned lessons for builders at every stage.

One of the early peaks came from defying conventional wisdom. Rather than waiting for perfect product-market fit from a single product, Jeff pushed to launch a second product in Twilio’s early days. I’ve taken a similar stance in my own work: when customer signal is strong and the surface area is adjacent, a thoughtfully scoped second product can accelerate learning, diversify revenue, and strengthen the platform story — as long as you preserve focus with crisp strategy, clear ownership, and a rigorous roadmap.

But no ascent is without valleys. A pivotal low point arrived when one of Twilio’s biggest customers, Uber, significantly scaled back their investment in Twilio’s products. Every product leader knows the sting of concentration risk — when a single customer’s shift reverberates across forecasts, roadmaps, and morale. The real lesson is how you respond: deepen value for the broader customer base, rebalance your portfolio, and institutionalize dependency reviews so one customer’s change doesn’t become an existential threat.

Jeff’s operating system also reflects a powerful inheritance from Amazon: a bias to “write it down.” I share this conviction. Clear, written narratives clarify assumptions, expose trade-offs, and make decisions auditable over time. It’s why “PowerPoint is a terrible decision-making tool.” Slides may persuade; writing forces us to think. In my teams, we prefer narrative memos, PR/FAQ-style artifacts, and decision logs to drive alignment, speed, and accountability.

Inside the C-suite, Jeff instituted practices that many product organizations underutilize. They run post-mortems when things go right — not just when they go wrong. In my experience, reverse-engineering wins reveals the leading indicators and repeatable behaviors that often get lost in celebratory moments. Equally important, Jeff had an “aha” moment that his executive team needed to argue more. Healthy debate is not dysfunction; it’s a prerequisite for durable decisions. The goal is principled dissent, time-boxed contention, and a clear decision owner — then unwavering commitment to execution.

For company-builders across industries and growth stages, these patterns are universally applicable: expand thoughtfully, manage risk before it manages you, privilege writing over slides, study your wins, and cultivate constructive conflict. That’s how you turn peaks and valleys into durable operating rhythms that scale from product-market fit to public markets.

If you want a deeper dive into Jeff’s philosophy on engineering leverage and developer-first cultures, his book “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” is a practical field guide: https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292

For a closer look at how Twilio operationalizes company values — including the famous “draw the owl” ethos — explore this overview: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have

You can follow Jeff on Twitter at @jeffiel.

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October 22, 2025
From Instacart to Anomalo: Elliot Shmukler’s Zero-to-One Playbook for Product Leaders

As a product leader who obsesses over data quality and founder-led GTM, I’m energized by Elliot Shmukler’s trajectory and the problem he’s tackling at Anomalo — which is a platform that validates and documents all of your data. After leading product and growth teams at Instacart, Wealthfront, LinkedIn, and eBay, Elliot stepped into the founder/CEO role to drive a true zero to one build. That arc offers a grounded blueprint for product management leadership, product-market fit, and disciplined execution.

In this conversation, Elliot’s most recent stop stands out: he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. Before that, he served at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay. That context matters because it informs how he now builds Anomalo with an eye for focused experimentation, clear value propositions, and operational excellence.

From my vantage point, the jump from executive to CEO resets the scoreboard. Elliot’s reflections on the zero-to-one phase mirror what I see in early-stage company-building: the need to aggressively prioritize time, protect founder focus, and qualify demand. He underscores a simple but costly trap I’ve witnessed too — wasting cycles on prospects who aren’t actually buyers. My playbook: define disqualification criteria early, insist on access to the economic buyer, require clear problem urgency, and time-box proofs of concept so founder energy fuels real pipeline, not vanity interest. This is classic founder-led GTM discipline and pays compounding dividends.

We also dig into how he picks extraordinary companies to work for. Elliot leans on sharp questions as a candidate and borrows decision-making frameworks from his poker playing. I resonate with that expected-value mindset: when stakes are uncertain, structure decisions around odds, outs, and downside protection. In product discovery, I translate that to staged bets, explicit kill criteria, and A/B tests that quantify lift before we scale. It’s a rigorous way to avoid narrative fallacy and to stay outcomes over output in OKRs.

Another thread that hits home: lessons from the best CEOs he’s worked with. The standout habits are crisp, frequent communication, transparent decision journals, and mechanisms that keep office politics at bay so the best ideas surface. In my teams, we pair written narratives with open metrics dashboards and “disagree-and-commit” rituals to reduce ambiguity and speed alignment. The result is faster feedback loops and clearer ownership across product roadmapping and sprint planning.

If you’re a founder in customer discovery, an executive eyeing your own startup, or an early-career builder trying to spot the next unicorn, there’s practical guidance here. You’ll find tactics for zero to one B2B marketing, qualifying enterprise demand, navigating product-market fit, and sharpening product management leadership skills you can apply today.

You can follow Elliot on Twitter at @eshmu.

To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager

And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

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October 22, 2025
From Zero Customers to IPO: Eric Berg’s Hard-Won Playbook for the Messy Middle

I’ve been revisiting the hard-won lessons behind durable product companies, and Eric Berg’s journey is a masterclass. Eric Berg is the CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.

From a product management leadership lens, the earliest chapters at Okta are a blueprint for zero to one B2B marketing and founder-led GTM. I break down his early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground, highlighting how tight product discovery, crisp problem statements, and ruthless prioritization turn ambiguity into product-market fit.

What stands out is the often-maligned “messy middle” — the stretch when traction exists but entropy expands. Eric’s moves on “moving upmarket” and evolving a “pricing and packaging model” are reminders that, when done well, takes a company to new heights. For SaaS pricing, I lean on value metrics tied to critical jobs-to-be-done, clear guardrails for discounting, and a win–loss feedback loop owned jointly by product and sales.

We then switch gears to team building and company building. The cultural patterns that stick with me: hire “folks up and down the org chart with the right ego to talent ratio” and operationalize a “disagree and commit” value so it’s not just a long-forgotten team motto. Practically, that means defining decision types (one-way vs. two-way doors), naming a DRI and approver for every call, time-boxing debate, and documenting the rationale so execution never stalls.

On execution mechanics, I’ve found that outcomes vs output OKRs paired with QBRs vs OKRs alignment creates a healthy cadence from strategy to delivery. When you layer in forward deployed engineers and structured customer advisory boards, feedback cycles compress without sacrificing focus — a powerful pattern in both product roadmapping and sprint planning.

Finally, the perspective shifts “as he approaches one year of sitting in the CEO seat” underscore the difference between building products and building a business. Capital strategy, talent density, and narrative become first-class product surfaces. As a product creator, I translate this into designing org APIs, setting explicit burn-to-learn budgets, and treating pricing, packaging, and GTM as core parts of the product.

If you’re navigating product-market fit lessons, wrestling with “moving upmarket,” or recalibrating SaaS pricing, this playbook maps the trade-offs from 0 customers through the “messy middle” and beyond. It’s a grounded field guide for product folks and operators who want to scale with clarity, strengthen culture, and accelerate learning without losing the thread.

Inspired by this post on First Round.

October 22, 2025
Ask Why It Won’t Work: Hard-Won 0→1 Lessons, Pre-Mortems, and Founder-Led GTM from Persona

I recently sat down with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital. As someone who leads product teams and thinks deeply about product-market fit and go-to-market, I was eager to unpack the 0 to 1 thinking behind Persona’s trajectory.

Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. For anyone operating in B2B SaaS, that’s the kind of signal you can’t ignore.

In our conversation, one theme stood out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, he brings this mindset to every aspect of running Persona. I share that instinct — when we anchor on “why it won’t work” early, we surface edge cases, stress-test assumptions, and prioritize outcomes over output. It’s a product discovery discipline that keeps teams honest and accelerates product-market fit lessons.

Rick also shared counterintuitive practices that resonated with my own founder-led GTM experiences. His engineers sell and cold-email prospects, and he doesn’t try to convince candidates that Persona is a company that will change the world. That may sound unconventional, but it’s exactly the clarity zero-to-one companies need: tight customer feedback loops, direct exposure to objections, and authentic hiring that screens for fit over hype. In my experience, these choices reduce handoffs, sharpen messaging, and create a culture that learns faster than the market moves.

There’s a broader leadership lesson here for product management: treat pre-mortems as a muscle, not a meeting. I apply this to hiring scorecards, roadmap bets, and go-to-market plays — explicitly listing failure modes, customer objections, and “anti-personas” who won’t buy. When we teach engineers to engage customers directly, we’re effectively building forward deployed engineers who carry context from discovery to delivery to launch, closing the feedback loop and improving zero to one B2B marketing execution.

For founders, engineering leaders, and hiring managers, the takeaways are practical: start with the “won’t,” design for objections, and let builders meet buyers early. Pair this with a clear definition of success metrics and a bias for candid, frequent iteration. The result is a stronger compass for product management leadership and a far more resilient go-to-market motion.

You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/

Inspired by this post on First Round.

October 22, 2025
My Battle-Tested Comms Playbook: Kill Bad Stories, Create Categories, Lead With Clarity

I recently sat down with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO. As I reflected on our discussion, I kept coming back to how closely great communications strategy mirrors great product strategy: clarity of narrative, ruthless prioritization, and the courage to reshape the market when the existing frame doesn’t serve customers.
What resonated most with me as a product leader was Shannon’s philosophy that comms is a strategic lever — and one of the most underappreciated functions. We dug into the practical side of the craft, from killing stories and creating new categories to the frameworks she uses for building relationships with reporters. The parallels to product management leadership are striking: define the problem space, choose the story you will not tell, and architect the environment where your best story can win.
On story killing, I’ve learned to treat narrative debt like technical debt. If a storyline no longer advances the strategy, I stop feeding it — even when it’s tempting to chase short-term attention. Shannon’s lens sharpened my own: identify legacy narratives that siphon focus, set a clear “no-story list,” and redirect energy to the few messages that compound. This is as much about leadership as it is about PR — our teams take their cue from the narratives we choose to reinforce (or retire).
Category creation is where comms and product strategy truly converge. When we define a category, we define evaluation criteria for buyers, shape the problem statement, and set the language for the market. In my experience, this only works when it is anchored in real customer pain and a credible roadmap. Shannon’s approach aligns with zero to one B2B marketing: validate the need, name the space with precision, and build proof that makes the category feel inevitable.
On media relationships, I subscribe to Shannon’s view that trust is a product you build over time. My framework is simple: be useful, be brief, be accurate. Offer real data, context, and accountable sources; say less and deliver more. The goal isn’t to “pitch” reporters — it’s to become a reliable operator who helps them tell truthful, timely stories. That reputational equity pays off when the stakes are high and nuance matters.
We also covered leadership arcs and career selection. Shannon’s perspective on choosing companies — align with mission, quality of leadership, and the clarity of the strategic hill to climb — mirrors how I evaluate product bets. Her transition from head of comms to CMO reinforced a lesson I’ve felt in my own roles: the first 100 days are about listening with intent, writing down the strategy, and operationalizing quick wins that build momentum. I also appreciated the nod to lessons from mentors and bosses like Jeff Weiner — durable leadership principles travel well across functions.
Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/
You can follow Shannon on Twitter at @sstubo.

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October 21, 2025
From Hair-on-Fire Problems to Product-Market Fit: Inside Pilot’s Human+Machine Playbook

I recently sat down with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. Before Pilot, he co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014. As a product leader, I was especially interested in his repeatable frameworks for idea validation and building conviction.

We focused on the earliest days of Pilot. Waseem took me behind the scenes of the ideation stage and walked through how the founding team gained enough conviction to actually start building. He also explained why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers. That hybrid approach resonated with me because it aligns technology leverage with trusted, high-touch service where precision and context matter.

From a product discovery perspective, I mapped his approach to a few principles I use with my teams: define the problem boundary tightly, de-risk the riskiest assumptions first, and run short learning loops that translate directly into product decisions. In Pilot’s case, the early tests weren’t about flashy features—they were about proving that a human-plus-software workflow could reliably deliver accuracy, speed, and peace of mind to finance leaders at startups.

We then dug into building Pilot’s ICP and getting the product into the hands of paying customers. Waseem shared practical tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. I’ve found similar tactics effective: insist on clear stakes and urgency, test willingness to pay early, and probe for budget ownership and implementation appetite. When discovery is anchored in real pain and committed timelines, founder-led GTM becomes a force multiplier.

Looking ahead, he outlined how he prioritizes which offerings to add to Pilot’s product suite. I appreciated the disciplined focus on adjacent problems where the core strengths of the human plus machine model create an unfair advantage. This mirrors my own product roadmapping lens: measure outcomes over output, earn the right to expand by nailing the core job-to-be-done, and stage extensions that compound value for the same ideal customer profile (ICP).

If you’re a founder—or aspire to be one—there’s a clear playbook here: validate ideas by stress-testing real urgency, crystallize your ICP early, and use learning-driven iterations to progress toward product-market fit. For product pros, the takeaway is to balance operational excellence with software leverage, and to let customer pain—not feature ambition—set the pace. Pilot’s journey offers crisp, repeatable patterns for zero-to-one execution and beyond.

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October 21, 2025
Confidently Validate Product-Market Fit Before You Build: Inside UserLeap’s Playbook

I’m obsessed with validating product-market fit before writing a single line of code. Studying Ryan Glasgow’s journey as founder and CEO of UserLeap — a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster — sharpened my own playbook for testing demand early and de-risking execution.

Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat). That operating rigor shows up in how he navigated the pre-build phase — a period I pay particular attention to when coaching teams through product discovery.

I rewind the clock to the 6-month period before launch, when I’m validating the idea and assessing a crowded market. This is where segmentation and early customer conversations do the heavy lifting. I make the target user painfully specific, probe for desired outcomes, and pressure-test willingness to pay. Just as importantly, I avoid common product/market fit mistakes: over-indexing on feature requests, conflating enthusiasm with intent, and skipping a clear hypothesis about the job-to-be-done.

From there, I frame the first version of the product as the smallest coherent solution that proves the value thesis. I outline how to think about adding new features — through evidence-based prioritization, not wishlist drift — and how UserLeap’s 3 product principles can guide day-to-day product decisions so the roadmap compounds rather than sprawls.

As a self-described “product guy,” I taught myself founder-led sales, including the specific tactics that made the biggest difference and how I’ve refined my approach into a repeatable playbook. That means running tightly scoped discovery calls, qualifying ruthlessly, using problem-centric demos, and turning every objection into a testable learning.

There’s also a simple question I always ask in customer meetings that unlocks clarity: “What would make this an absolute no-brainer for you in the next 30 days?” It anchors the conversation in outcomes, timelines, and trade-offs — the raw material for reliable product-market fit signals.

For the curious builders, here are the books that have most influenced my approach to product discovery, roadmapping, and founder-led GTM: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick; You Can’t Teach a Kid to Ride a Bike at a Seminar by David Sandler; and User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton.

You can follow Ryan on Twitter at @ryanglasgow.

If you’re navigating product-market fit right now, use these tactics to sharpen segmentation, run higher-signal customer conversations, and build a first version that earns traction fast — then scale with a repeatable founder-led GTM motion.

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October 21, 2025
No UX Research Team? Proven Playbook to Validate Problems, Prototype Smart, and Nail Pricing

I recently sat down with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. I set out to distill a practical playbook any product team can apply — even if you don’t have a formal UX research function.

Jane tackles the thorniest customer development questions and walks through an end-to-end research process that works in the real world: clarifying your goals, asking the right questions, selecting participants, and synthesizing insights. I translate these steps into repeatable product discovery rituals that drive better decisions and faster product-market fit.

We start by applying her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. I share how I scope lean studies, use founder-led GTM interviews to deeply understand the problem we’re solving, and shape hypotheses for competitive versus greenfield markets, including how to size demand and figure out willingness to pay for SaaS pricing.

We also dig into best practices for prototyping and iterating. I show how I pair lightweight prototypes with clear research questions, time-box sprints, and convert insights into product roadmapping and sprint planning that truly move the needle.

Later, we confront common roadblocks: building for multiple users, aligning personas, and what to do when people aren’t excited about your product or using it frequently. I outline tactics to diagnose the gap — value proposition, onboarding, activation, and retention — then adjust the solution, messaging, or usage triggers to rebuild momentum.

If you want to go deeper, here’s the book Jane referenced: Just Enough Research by Erica Hall. I also recommend her article: What’s the point of a UX research team?

Whether you’re talking to potential customers before you start a company or looking to get better feedback from your current users, this conversation is packed with field-tested practices for founders, product-builders, and design folks alike. Use it as your starting point to run credible UX research, de-risk decisions, and accelerate product-market fit without a dedicated team.

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October 21, 2025
Mastering Operational Complexity: Building Thirty Madison Without Upside-Down Unit Economics

Operationally-intensive businesses can be unforgiving if you don’t design for unit economics from day one. That’s why I was eager to dig into the playbook behind Thirty Madison and its approach to marrying operational excellence with disciplined financial fundamentals.

I sat down with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions. The company’s product and operations choices offer a compelling case study for product leaders who need to scale real-world services without sacrificing margins or customer experience.

After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation.

We got into the realities of building an operationally complex business with a physical or real-world component. I’ve led product and operations through similar constraints, and I appreciated how Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. The throughline: pair a crisp problem definition with an operating model that earns its margins every day.

He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In my experience, this is the difference between a growth engine and a leaky bucket.

We then moved to team design — the people mechanics that make operational complexity manageable. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. I shared my own approach: probe for judgment under ambiguity, appetite for continuous improvement, and the discipline to instrument every step of the customer journey.

My takeaway for product leaders: treat operations as a first-class product. Pressure-test the model with conservative assumptions, validate every cost driver, and identify the inventive moves that unlock margin at scale. Keep the customer experience and the P&L in the same conversation, and hire operators who think like product managers and product managers who respect operational constraints. That’s how you build an operationally-intensive business without ending up with upside down unit economics.

Inspired by this post on First Round.

October 21, 2025