Tag: product discovery

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.

Inspired by this post on First Round.

October 22, 2025
Inside Product-Led Growth: Self-Serve, Pricing, and Prioritization Lessons from Kate Taylor

I recently sat down with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce. That trajectory alone offers a rare, end-to-end vantage point across product-led growth, scaled sales, and customer experience — precisely the intersection where modern SaaS wins or loses.
In our conversation, Kate shared a wealth of advice for building out product-led growth and self-serve motions. She shared tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from. As someone who has built PLG and hybrid motions, I found her guidance both pragmatic and immediately applicable — especially for teams balancing self-serve efficiency with enterprise demands.
We went deep on product prioritization. At Notion, their system of 700 tags enables a rigorous, multi-dimensional view of customer needs and product work. Hearing specific examples of tradeoffs they’ve had to navigate reminded me how essential it is to pair qualitative signal with quantitative usage data — and to operationalize that insight in product roadmapping and sprint planning. My takeaway: a well-structured tagging and feedback taxonomy is a force multiplier for product discovery and product-market fit lessons.
We also explored pricing and packaging — from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based. That philosophy reframes trials around value realization and activation, not arbitrary timelines. In my experience shaping SaaS pricing, this approach improves conversion and long-term retention when you align paywalls to “aha” moments and clear outcomes. It’s a call to design pricing alongside onboarding, not after it.
Customer experience was another rich vein. We discussed how to handle a wide range of use cases while building the “front door” customer experience her team envisions. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate’s perspective elevates support from a cost center to a strategic insight engine. I’ve seen the same: the best CX loops feed product planning, reduce churn, and strengthen go-to-market alignment.
We closed on leadership. Kate unpacked why she hires for curiosity, how she teaches teams to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style. The throughline is deliberate learning: create environments where product managers and operators can test, reflect, and iterate quickly — the same principles that make PLG work at scale.
If you’re building or refining a product-led, self-serve motion — or moving upmarket without breaking what already works — these insights on prioritization, pricing, and customer experience provide a clear blueprint. My advice: operationalize feedback, pressure-test your packaging against value moments, and treat support as your highest-signal discovery channel. That’s how you turn strategy into compounding growth.

Inspired by this post on First Round.

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

Inspired by this post on First Round.

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
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/

Inspired by this post on First Round.

October 22, 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 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
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.

Inspired by this post on First Round.

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.

Inspired by this post on First Round.

October 21, 2025
From Painful Pivots to Product/Market Fit: 0→1 Lessons I Drew from Rupa Health’s CEO

I recently reflected on a candid conversation with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As I listened to her zero-to-one story, I mapped each pivot to familiar product/market fit lessons I see across founder-led GTM and product discovery.
For the first half of her journey, I paid particular attention to the elusive startup holy grail of product/market fit. The aha moment that the first iteration of the product wasn’t going to work arrived quickly and unmistakably. Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one — a thread that resonates deeply with my experience in product management leadership.
One takeaway that stood out: why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. In the hunt for PMF, premature hiring can dampen learning velocity and blur signal. My playbook is to stay lean, keep customer feedback loops tight, and lead with founder-led GTM until retention and engagement data justify scale.
We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path. I think of these as “stepping-stone” bets: purposeful experiments that expand your surface area for learning, even if they’re not the final destination. Done well, they accelerate discovery, de-risk strategy, and set up the next high-conviction move.
In the second half, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead. In my practice, I often swap static descriptions for outcome-based scorecards and paid trial projects to align expectations with the realities of 0→1 execution.
As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur. For product leaders, the through-line is clear: protect speed, test boldly, hire carefully, and let evidence — not ego — pull you toward product/market fit.
You can follow Tara on Twitter at @taraviswanathan.
To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.”

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October 21, 2025
From Developer to CMO: Archana Agrawal’s Airtable & Atlassian Playbook for Product‑Led Growth

I recently sat down with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. She joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. As someone who leads product teams and partners closely with go-to-market, her cross-functional vantage point immediately resonated with me.

We began by unpacking the messaging challenges of horizontal products like both Airtable and Atlassian. I’ve learned firsthand that breadth can blur the story if you don’t anchor it to a clear persona and set of jobs-to-be-done. Archana’s approach to narrowing in on the right persona while preserving platform flexibility mirrors how I guide positioning: focus on the core workflows that deliver immediate value, then layer in industry-specific outcomes and proof points. That balance keeps the narrative sharp without constraining the product’s surface area.

From there, we dove into the close interplay between product and marketing teams, particularly for product-led growth companies. We aligned on a principle I hold deeply: discovery signals, activation patterns, and in-product usage should directly shape go-to-market. When product and marketing share adoption, retention, and expansion metrics, it creates a single operating system for decision-making. The result is tighter feedback loops, smarter experimentation, and a more durable growth engine.

Organizational design was another major theme. We discussed how to set teams up to break down siloes and foster experimentation through shared roadmaps, clear decision ownership, and transparent operating cadences. As CMO, she oversees all the different marketing functions that report up to her and has established rituals for keeping a pulse on what most deserves attention. In my own practice, lightweight, recurring checkpoints across product and marketing create the psychological safety to test, learn, and rapidly scale what works.

While today’s conversation is of course a must-listen for marketers, I’d argue the insights are equally valuable for product, sales, and executive leaders navigating horizontal SaaS. As a former engineer-turned-marketer, Archana brings a unique, data-driven perspective to prioritization, experimentation, and storytelling—one that complements how I think about product management leadership and cross-functional alignment.

If you’re building in a product-led growth motion or stewarding a horizontal platform, you’ll find pragmatic ideas here: sharpen persona definition without losing breadth, align product and marketing on shared metrics, design rituals that surface the highest-leverage work, and cultivate a culture where experimentation is expected. These are the foundations that compound, regardless of company stage.

Inspired by this post on First Round.

October 21, 2025