Month: October 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/

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October 22, 2025
From Slack’s ‘Where Work Happens’ to CEO: Inside the Product Strategy That Scales

I’m drawn to leaders who bridge marketing excellence with rigorous product management. Kelly Watkins, CEO of Abstract, exemplifies this. Abstract is a platform for structure and transparency in the design process. What makes her journey distinctive is the transition from a marketing background into the CEO seat — a path that demands both narrative mastery and operational discipline.

Reflecting on her first year as CEO, what stood out to me was her alternative to yearly planning, borrowing from famed military strategist John Boyd. I’ve wrestled with annual planning cycles myself, and this approach resonates with how I guide product roadmapping and sprint planning — shorter feedback loops, tighter decision cycles, and a bias for learning over lengthy forecasts. It’s a pragmatic way to keep teams focused on the right problems at the right time.

Her walkthrough of Abstract’s most recent product launch crystallized a leadership stance I value deeply: constantly optimize for trade-offs, rather than chasing clear-cut right and wrong. In my experience, framing decisions as explicit trade-offs elevates cross-functional collaboration, aligns product discovery with realistic constraints, and encourages outcomes over output. It’s the difference between shipping features and shipping meaningful progress.

Drawing on a storied marketing career at Slack, Github, and Bugsnag, she underscores a jobs-to-be-done approach for crafting a product story when there’s loads of competition. I’ve seen JTBD unlock clarity when teams get lost in feature parity — it centers the product on the customer’s progress, not our roadmap. When the market is noisy, a crisp jobs-based narrative becomes a durable strategic asset.

The behind-the-scenes look at developing Slack’s “where work happens” tagline is a powerful reminder that great positioning anchors to the job, not the jargon. Moving from a passionate early adopter base to a ubiquitous product requires more than demand gen — it requires crossing the chasm with a value story that scales. I’ve found that the leap from early signals to broad adoption hinges on consistent messaging, intentional onboarding, and instrumentation that proves product-market fit beyond the initial cohort.

This conversation isn’t just a must-listen for marketing folks; it’s a primer for any leader seeking to collaborate more effectively across the org. The art and science of marketing become a force multiplier when paired with disciplined product management leadership. For teams navigating zero to one B2B marketing, these lessons translate directly into sharper execution and clearer decision-making.

My takeaways are straightforward: plan in adaptable cycles, not rigid annual cadences; embrace trade-offs as a core leadership tool; use the jobs-to-be-done framework to tell a product story that cuts through competition; ground your tagline in the customer’s real job; and design your path from early adopters to the mainstream with intention. Applied together, these principles turn strategy into momentum and momentum into enduring growth.

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October 22, 2025
Go Unreasonably Deep, Stay Naive: Irving Fain, Bowery Farming, and a $300M Leap

I recently revisited the journey of Irving Fain, founder and CEO of Bowery Farming, and it reinforced a product leadership mantra I live by: preserve beginner’s mind while going exceptionally deep on the problem. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company. Bowery’s mission to democratize access to fresh, locally grown food. That’s an enormously complex challenge, and what makes it even more compelling is that Irving didn’t come from agriculture. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio. As a product leader, I’ve seen how crossing domains can unlock first-principles thinking that incumbents often overlook. Looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In my experience, that combination—breadth of exploration and ruthless depth—separates breakthrough products from incremental ones. I especially appreciate his discipline of paying just as much attention to the doubters as to the folks who believed in the vision. When I’m validating a thesis, I interview skeptics first, pressure-test assumptions, and map out what would have to be true for the idea to work. A multi-pronged discovery approach like Irving’s is a playbook I recommend often: define the problem in user language, list the riskiest assumptions, seek disconfirming evidence early, and prototype thin slices that target the biggest unknowns. This is how you de-risk complex systems—whether it’s indoor farming or enterprise SaaS—by turning ambiguity into an ordered queue of learnable risks. What also stood out to me was the rigor in assembling Bowery’s small-but-mighty team of five. He kept the team deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. In early product stages, I hire for rate of learning, adjacent technical depth, and cognitive diversity. Small teams move faster when they share a clear outcome, a strong culture of experimentation, and the freedom to question every constraint. For founders, product leaders, and ambitious ICs contemplating the leap, this story offers both inspiration and practical guidance: protect naivety, operationalize first principles, and build a team that learns faster than the problem evolves. The $300M milestone is a signal, but the real lesson is the system that produced it—unreasonable depth, disciplined discovery, and a culture unafraid to rethink the field from the ground up. You can follow Irving on Twitter at @ifain To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

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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
From Dozens to Thousands: The People-First Playbooks and Pitfalls I’ve Learned to Avoid

I recently sat down with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund. As someone who has scaled product and go-to-market organizations, I wanted to surface the real-world playbooks and pitfalls that shape employee retention at startups.

We focused on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We compared the moments to draw from established playbooks in the people space versus the moments to start from first principles. I especially appreciated how she brings a data mindset to the people space, including designing a sophisticated attrition model—a discipline I’ve found invaluable for aligning capacity planning, product roadmaps, and outcomes vs output OKRs.

Next, we tackled the questions I hear most from startup founders and product leaders alike: whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews. I shared where I’ve seen levels unlock clarity for IC to manager transition, and where premature structure can slow execution. We aligned on making performance reviews a continuous, signal-rich system that strengthens product management leadership and retention, rather than a once-a-year formality.

We also explored the broader role companies play in today’s employee experience—from the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind. My takeaway: culture is a product you ship every day, and your early decisions about norms, accountability, and transparency compound as you scale from dozens to thousands.

If you’re building or leading teams, this conversation is a practical field guide. It’s relevant for HR leaders, founders, and cross-functional partners in product, engineering, and go-to-market who want an inside look at what’s top of mind for people leaders today—and the systems behind the scenes that power startups to reach new heights. Expect actionable insights you can apply in weekly rituals, hiring loops, startup compensation strategy decisions, and org design.

Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838

Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836

Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet

You can follow McKenna on Twitter at @mckmoreau

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October 21, 2025
From Dropbox to Loom: Hard-Won, Sales-Driven Product Lessons for Competitive Markets

I recently sat down with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. As a product leader, I’m always looking for the connective tissue between sales insights and product strategy, and Sam’s journey offers a rich playbook for product-led growth, enterprise sales, and go-to-market execution.

We started with his earliest experience at Dropbox, and I was struck by his aha moment that sales is an insight driver. That framing resonates deeply with how I run discovery and roadmap governance: when sales becomes a structured listening post, it sharpens pricing and packaging decisions and helps prioritize the feature roadmap as Dropbox moved up market. In practice, that means operationalizing feedback loops, pairing usage telemetry with win–loss analysis, and iterating packaging to match how customers actually buy and expand.

Reflecting on his time at Quip, Sam shared what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also walked through tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. My takeaway for product teams: differentiation must be engineered, not just messaged. Equip champions with crisp value proof, remove switching friction in the product, and align your roadmap to moments that neutralize incumbent advantages. In other words, design the product to win the deal before the demo even starts.

Turning to his current role at Loom, Sam is threading all of those experiences together. He emphasized his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” I loved the practicality here: a tight sales–product cadence, shared metrics for activation and expansion, and packaging that scales from self-serve to enterprise without creating friction. “Everyone wants a silver bullet,” but the real edge comes from compounding small, well-orchestrated decisions across pricing, roadmap, and enablement.

If you’re in sales, Sam’s path reinforces how to translate field signals into product change that moves pipeline and retention. And if you work in a product-led growth company, you’ll come away with a clearer understanding of how sales fits in: establish a reliable voice-of-customer loop, treat SaaS pricing and packaging as a product, and use product roadmapping to align with the most material customer problems. That’s how you turn insights into impact—and how product and sales win together in competitive markets.

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October 21, 2025
Inside the Engineering Cultures of Microsoft, Reddit, Looker & Twitter: Hard-Won Lessons

I’m endlessly fascinated by how engineering culture shapes product velocity, quality, and leadership outcomes. Drawing on lessons from Nick Caldwell’s journey, I’ve distilled the practices that consistently produce performance, clarity, and cohesion across teams. These are the ideas I reference when coaching product and engineering leaders, building org structures that scale, and aligning teams around outcomes.

Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.

Across Microsoft, Reddit, Looker, and Twitter, the cultural contrasts are stark—and incredibly instructive. I focus on how each environment sharpened a different leadership muscle: designing resilient organizations, navigating high-context communities, aligning product and engineering at scale, and translating mission into execution. The net effect is a practical playbook for product management leadership, manager development, and cross-functional collaboration.

From Microsoft, I take to heart what Nick believes is a massively underrated approach to organizational design. The company’s disciplined cadence of regular pruning and shaping the org chart keeps accountability crisp and prevents drift. Their management training and talent development systems create durable leadership pipelines, while what Nick calls the fairest performance review system he’s seen sets a predictable bar for growth. In my own practice, I mirror these principles with explicit role charters, outcomes vs output OKRs, and routine structure audits that keep teams mission-aligned.

Transitioning from a 15-year tour at Microsoft to Reddit came with a steep learning curve—and that resonates deeply with anyone making a big career move or an IC to manager transition. Nick’s advice maps closely to what I coach: re-anchor on the company’s narrative, over-communicate intent, and recalibrate decision speed to the culture. At Reddit, the mission-driven culture isn’t just branding; it informs how influence is earned and how leaders show up. That lens carries forward to leadership at Twitter, where connecting daily execution to mission keeps product and engineering grounded and resilient through change.

Looker offered a rare vantage point: leading both product and engineering. The result is a masterclass in reducing friction between two orgs that are often at odds. The insights I apply: define a single operating rhythm for product roadmapping and sprint planning, eliminate ambiguous ownership, and measure joint outcomes rather than siloed outputs. When product strategy, discovery, and delivery operate on one shared cadence, you unlock faster decisions, fewer handoffs, and cleaner accountability.

For managers looking to level up, these lessons are actionable: invest in management training, make performance systems transparent, prune org complexity before it compounds, and tie every roadmap bet to mission and measurable outcomes. For engineers eyeing leadership, study how culture sets the rules of engagement—then learn to translate that into decision frameworks, communication habits, and hiring signals that reinforce your product and engineering alignment.

This is a wide-reaching set of takeaways because the problems are universal: how to design organizations that scale, grow leaders systematically, and build cultures where product and engineering don’t just coexist—they compound each other’s strengths. If you’re rethinking your org chart, refining your OKRs, or preparing for your next leadership transition, these practices will give you a durable edge.

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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
Retaining Startup Talent: Conflict Playbooks and Couples Therapy Tactics I Use

I recently sat down with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care. As someone who leads product management and cares deeply about culture, I wanted to unpack what truly keeps startup employees engaged and growing over the long haul — and how people leaders can partner with product leaders to make that happen.

Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled. That vantage point matters: when HR business partners and product leaders operate as one team, we can proactively design the org, clarify decision rights, and align incentives so people can do the best work of their careers.

We began with conflict resolution at work — a topic that shows up in every scaling startup. Alex talked through patterns she’s seen and why borrowing from couples therapy can be surprisingly effective. I’ve found the same. Techniques like mirroring to ensure each person feels heard, naming feelings before jumping to fixes, and agreeing on shared norms (“assume positive intent,” “disagree and commit,” “no surprises”) defuse tension fast. When I coach PMs and cross-functional leads, I push for structure: time-boxed turn-taking, clear owners for decisions, and a quick retro to repair after conflict. These are the same muscles healthy relationships use — empathy, curiosity, and accountability.

We also dug into the challenge of getting employees to stick around long-term at startups. Retention is rarely about perks; it’s about momentum, meaning, and mastery. From hiring your own boss to navigating tough career conversations, Alex’s playbook resonated with mine. I encourage leaders to draft a “growth contract” with each team member: What capabilities are you building this quarter? What scope will expand if you nail it? What support do you need? When someone hires their own boss, I frame it as a capability accelerator — you’re trading title for a teacher, and the compounding effect on your craft can be huge.

Her own journey — rising through the ranks from IC to exec at Flatiron — offers a blueprint for the IC to manager transition many product folks face. My guidance: don’t rush the leap. First expand scope as an IC (own bigger outcomes, not just features), then practice leadership without authority (drive cross-functional programs), and finally formalize people leadership when the org truly needs it. In product management leadership, that sequencing prevents the common trap of managing without mandate or mission.

Alex has also seen the growing pains of scale up close — and I’ve lived them, too. On day one in a new role, you’re “selling” your new role with an elevator pitch when you first join, because clarity reduces friction. I write a crisp one-liner on why the role exists, the problems it owns, and how success will be measured, then socialize it relentlessly. Just as important is resisting the danger of locking into people processes and frameworks too early. I favor lightweight experiments: pilot a performance ritual with one org, run a compensation calibration dry run, or test a feedback cadence in a single squad before scaling. Evolution beats edict.

Across all of this, the throughline is simple: great people leadership and great product leadership share the same foundation — clear outcomes, frequent feedback, and respect for the human at the center of the work. Whether you lead engineering, design, product, or people, these principles help teams compound trust and results.

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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