Tag: product-market fit lessons

Behind the Scenes of Canva’s Meteoric Rise: Zach Kitschke’s Battle-Tested Playbook

I’ve been reflecting on the story of Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. As a product leader, that trajectory is a masterclass in product management leadership, product-market fit lessons, and deliberate go-to-market execution.

Zach was one of Canva’s first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function. That range resonates with my own experience in high-growth environments: early operators wear many hats to unblock the work and accelerate learning loops.

This career history gives Zach a unique vantage point on why Canva worked. I zero in on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators. To me, the insight is simple and powerful: obsess over a clear initial ICP, deliver undeniable value for content creators, and let word-of-mouth amplify your early wins. That’s product discovery in action, supported by tight product roadmapping and sprint planning that prioritizes outcomes over output.

Next, I dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun. These practices make culture operational: they align teams on strategy, reduce ambiguity, and create repeatable rituals that sustain speed without burning people out.

From a leadership lens, I appreciate how these mechanisms turn tacit knowledge into shareable playbooks. Vision decks codify narrative; strategy docs create traceability; the skills framework clarifies expectations for IC to manager transition; and the ‘chaos to clarity’ spectrum gives product teams a shared language to navigate uncertainty. This is the scaffolding great product organizations rely on to scale quality, autonomy, and accountability.

Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. I’ve found those two moves to be force multipliers: advisors compress time to insight, and timely succession unlocks what the business needs next. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone here.

You can follow Zach on Twitter at @zachkitschke.

Inspired by this post on First Round.

October 21, 2025
Inside Hubspot’s Build: Co-Founder Compatibility, IC Leadership, and Engineering Culture as Product

I was energized by the depth and clarity in this conversation. Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. From my vantage point leading product at HighLevel, Inc., I zero in on what product leaders can operationalize right away: co-founder alignment, deliberate operating systems, and engineering-driven culture.

Early in the discussion, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. As someone who has built and led cross-functional product organizations, I appreciated the rigor behind this compatibility testing—clear expectations, explicit decision rights, and pre-agreed escalation paths. My takeaway for potential founding pairs: align on values and working agreements up front to increase the likelihood of success and smoother sailing.

What keeps Dharmesh engaged after all these years are foundational building blocks that make the role intrinsically rewarding. I loved his approach to eliciting feedback through “bug reports.” Treating leadership behaviors and team processes like software defects creates a safe, systematic way to surface issues fast. Equally compelling is his decision to never take on any direct reports and remain an individual contributor as a co-founder; IC leadership can be a force multiplier when the organization designs clear ownership boundaries and high-bandwidth interfaces.

The most striking arc in the conversation is how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product. As a product creator, I resonate with this framing: culture needs a roadmap, measurable outcomes, and tight feedback loops—exactly the mechanisms we use to build world-class products.

For product leaders and founders, the practical playbook is clear: test co-founder fit early and explicitly, invite “bug reports” to de-risk blind spots, design IC leadership paths alongside managerial tracks, and engineer culture with the same rigor you bring to the product. These patterns improve product-market fit internally—within your org—long before they amplify results in the market. That’s the compounding advantage I aim to cultivate every day.

October 21, 2025
Scale Smarter: Buy vs Build, Core Focus vs Innovation—Hard-Won Insights with Zendesk’s CTO

I recently sat down with Adrian McDermott, CTO of Zendesk, for a candid conversation on how to scale product and engineering without losing the essence of what makes the product great.

Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. I’ve long admired how that trajectory blends product management leadership with operational rigor, and I wanted to unpack the systems behind it.

We began with the classic scaling fork in the road: double down on what’s working or make a change. In my experience, this decision rarely fits a simple binary, and I asked how he navigates it in practice. He went much deeper than the “what got you here won’t get you there” advice you hear all the time in startups, outlining how to read momentum, market signals, and organizational readiness before flipping a switch.

Next, we explored the tension between venturing into new product areas and keeping the central product brilliant. He shared how they use the zone to win frameworks at Zendesk. I contrasted that with my own approach to product discovery and product roadmapping and sprint planning: protect core experience quality with clear guardrails while allocating explicit capacity for bets that expand the addressable problem space.

We then dug into the evergreen dilemma of whether to build or to buy. He walked through the origin stories of several Zendesk products, from the wins to the lessons learned. His take on the role of competition in product strategy and his definition of a truly great product resonated with me. For my teams, I evaluate buy vs build decisions through a simple lens: strategic differentiation, speed to validated learning, total cost of ownership, and ecosystem leverage; if the capability isn’t core to our unique advantage, I bias to buy and integrate, then instrument relentlessly.

In the back half of our conversation, he shared what he’s learned leading both product and engineering teams, along with practical go-to-market lessons that shape how features actually land with customers. We ended on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and I appreciated the way he adapts hiring profiles and loops to the phase of scale—tight generalists early, then rigor around outcomes vs output as the organization matures.

If you’re scaling a SaaS product, you’ll find actionable insights here: how to avoid false trade-offs, decide when to preserve the core versus explore, operationalize zone to win frameworks, and make smarter buy vs build calls that accelerate learning and customer impact.

As a product leader, these lessons reaffirm a simple truth: sustainable growth comes from deliberate portfolio choices, clear go-to-market alignment, and consistent, values-based hiring that raises the quality bar with every new teammate.

Inspired by this post on First Round.

October 21, 2025
6 Early Marketing Missteps I See Founders Make — And Simple Fixes to Prevent Painful Launches

I’ve helped hundreds of early-stage startups build their positioning and brand strategy from the ground up, and certain patterns show up again and again. In this reflection, I’m sharing six early marketing missteps I see most often — plus the practical fixes I use with founders to sharpen positioning, clarify messaging, define brand personality, and orchestrate a high‑leverage launch strategy.
Early marketing can feel like changing the tires while the car is moving. You’re chasing product‑market fit while trying to define a category, articulate company purpose, and build a founder‑led GTM motion that actually converts. The good news: with a few repeatable exercises and a clear sequencing of work, you can avoid costly detours and get to traction faster.
Misstep 1: Chasing category creation too early. Defining a new category is tempting — it feels bold and visionary — but it’s often premature before you’ve nailed a sharp, undeniable problem. My fix: earn the right to a category by first winning a specific use case. Anchor your product positioning to an existing mental model customers already understand, then introduce the “newness” as a step‑change, not a wholesale reinvention. Category creation is a byproduct of repeated wins, not the starting line.
Misstep 2: Treating company purpose as a tagline instead of a true north. A purpose that doesn’t inform roadmap, pricing, brand personality, and go‑to‑market is just wall art. My fix: write a one‑sentence purpose that states who you serve, the change you enable, and why it matters — then pressure‑test every strategic decision against it. If it doesn’t help you prioritize features, target segments, or channels, it’s not actionable enough.
Misstep 3: Leading with emotional benefits while burying functional proof. Emotion matters for brand-building, but in the zero‑to‑one phase, customers buy outcomes. My fix: articulate a crisp value proposition that pairs functional benefits (time saved, errors reduced, revenue unlocked) with specific, credible proof points. Use customer‑validated messaging built from interviews, jobs‑to‑be‑done, and real usage data. Earn the right to emotion by proving the outcome first.
Misstep 4: Allowing brand personality to drift from the product and buyer. When brand voice doesn’t match the problem space or ICP, trust erodes. My fix: choose three core personality traits (for example: authoritative, pragmatic, optimistic) and define both what they are — and what they are not. Audit every touchpoint — website, onboarding, sales enablement, docs — to ensure consistency. This creates a brand people recognize and rely on across the funnel.
Misstep 5: Obsessing over other startup competitors instead of the status quo. The biggest competitor for most startups is inertia — spreadsheets, duct‑taped workflows, or “do nothing.” My fix: frame your positioning against the current workaround first. Show the switching ROI clearly, then differentiate from adjacent vendors. Use side‑by‑side comparisons that include the baseline status quo, not just other tools.
Misstep 6: Expecting PR to be a growth strategy. Launch theater can generate a spike, but it rarely produces sustained pipeline. My fix: treat launch as a process, not an event. Warm up your ICP with problem‑led content, customer stories, and social proof. Invest in owned channels (email, SEO, community) that compound. Set media expectations appropriately and measure what matters: qualified demand, activated users, and retained revenue.
To operationalize all of this, I use a simple positioning framework that keeps teams aligned: for [who], who [have this need], our [product] is a [category] that [delivers this outcome], because [proof]. Then we stress‑test with customers until the language is repeatable, the benefits are measurable, and the story is unmistakable across sales, marketing, and product.
If you want to go deeper into startup brand strategy, positioning, and messaging, I recommend these articles:
Positioning Your Startup is Vital — Here’s How to Nail It
Three Moves Every Startup Founder Must Make to Build a Brand That Matters
So You Think You’re Ready to Hire a Marketer? Read This First.
And here are books that sharpen the craft and expand your mental models:
Positioning: The Battle for Your Mind
Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets
Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life
Predictably Irrational: The Hidden Forces That Shape Our Decisions
Founders who avoid these traps — and sequence brand strategy, product marketing, and go‑to‑market with discipline — build momentum faster. Do less launch theater, more customer‑validated messaging. Less category hype, more proof. That’s how you create a brand that compounds.

Inspired by this post on First Round.

October 21, 2025
Mastering International Expansion: My Product Playbook Inspired by Faire’s CEO Max Rhodes

International expansion can be a powerful growth lever — or an expensive distraction. Through my product leadership lens, I’m always looking for patterns that separate the former from the latter. Recently, I reflected on insights from Max Rhodes to distill a practical, founder-friendly playbook for going global without losing focus.
Max Rhodes is the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. His vantage point is especially useful for product leaders scaling multi-sided marketplaces and navigating complex cross-border dynamics.
Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar.
In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.
After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. I found his decision framework refreshingly practical — a blend of timing, readiness, and strategic focus that maps well to the realities of product-market fit, capital efficiency, and operational maturity. I’ve used similar mental models to pressure-test when our roadmap should shift from depth in one market to breadth across many.
Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it. What resonated with me was the balance between a disciplined operating rhythm — clear goals, tight feedback loops, and cross-functional ownership — and a nuanced, market-by-market go-to-market strategy that respects local competitors and customer behaviors.
To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups I’ve leaned on this mindset during hypergrowth — encouraging PMs, GMs, and functional leaders to continually redesign their roles so we can scale scope without calcifying decision-making. The emotional lift is real, but the payoff is a more resilient organization that can execute across time zones and product surfaces.
Here’s how I translate these lessons into an actionable international expansion checklist for product leaders: validate pull (authentic customer demand and repeatable GTM motion), ensure supply and liquidity for marketplaces, map the competitive landscape by customer jobs (not features), stand up a clear operating cadence with measurable outcomes (not just output-based OKRs), hire for local context and cross-functional ownership, and define a fast, lightweight process for localizing product, pricing, and support. When those pieces click, international expansion compounds rather than distracts.
You can follow Max on Twitter at @MaxRhodesOK.

Inspired by this post on First Round.

October 21, 2025
Never Done Sales? Proven GTM Playbooks I Learned from Meka Asonye at Stripe & Mixpanel

I recently sat down to unpack practical go-to-market lessons with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. As someone who lives at the intersection of product management and revenue, I was eager to explore how his operator playbooks translate into founder-led GTM, early pilots, customer success, and the first sales hire.

Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. This trajectory grounded our conversation in the kind of zero to one B2B marketing and sales context that founders and product leaders wrestle with every day.

In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. As I listened, I kept mapping his approach to the product discovery rituals my teams use: clarify the problem in the customer’s words, validate urgency with real-world triggers, and close the loop with crisp next steps. When early calls stall, I look for the same failure modes he flags — muddy ICP definition, solutioning too early, or skipping mutual action plans — because those blind spots ripple into product-market fit lessons later.

He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. I’ve made similar tradeoffs: hire athletes over specialists too soon and you risk inconsistent execution; hire too senior too early and you can overfit process to a still-evolving product. I probe for pattern recognition in discovery, deal hygiene, and collaboration with product — then validate with back-channel references that speak to coachability and grit. On comp, we aligned on anchoring incentives to leading indicators you can measure post-onboarding (pipeline quality, conversion at key stages, and time-to-first-win), rather than chasing lagging revenue alone.

We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. My litmus test: a strong design partner has painful, frequent use cases, access to decision-makers, and a bias toward co-building — without asking you to contort your roadmap into bespoke work. If your ICP is squishy, pilots turn into unpaid consulting; if it’s crisp, you get signal on packaging, onboarding, and the reliability thresholds that unlock renewal.

We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. I see the same pattern: founders over-index on acquisition and underinvest in outcomes. The antidote is early, proactive customer success that operationalizes value moments — onboarding checklists, success plans tied to business metrics, and regular health reviews — so renewal is earned long before it’s negotiated. This is where founder-led GTM compounds, turning hard-won pilots into durable references.

Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. What stood out to me was the throughline: the same curiosity, discipline, and customer empathy that drive outstanding sales and product outcomes also make for thoughtful investors — especially those helping founders navigate the messy middle between idea and repeatable GTM.

If you’re building from zero, here’s how I’m applying these takeaways with my teams: structure first conversations around problem clarity and next steps; define your ICP tightly enough to say clear no’s; choose design partners who reflect your future ideal customers; treat customer success as a core GTM motion, not a support function; make the first sales hire with leveling discipline and reference rigor; and measure onboarding success with leading indicators that predict revenue. These are the small, repeatable habits that move you from searching for fit to systematizing growth.

Inspired by this post on First Round.

October 21, 2025
IC, Manager, or Founder? Amber Feng’s Playbook for High-Impact, 0→1 Engineering Careers

I recently dove into a compelling conversation featuring Amber Feng, the co-founder and CTO of Cocoon, who was previously an engineering leader at Stripe for eight years. As I reflected on her journey, I found actionable takeaways for anyone navigating an engineering career — whether you’re optimizing your IC craft, stepping into management, or exploring the founder path.

What resonated first was how her experiences span the full spectrum — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. I’ve seen similar arcs on my own teams, and the highest-impact engineers consistently share unexpected traits: they obsess over customer problems, communicate with crisp clarity, manage energy as carefully as time, and treat stakeholder alignment as a core skill. Those behaviors compound across levels, and they’re as valuable in product discovery as they are in product roadmapping and sprint planning.

We also get into the perennial debate many engineers face — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and her experience mirrors what I advise during the IC to manager transition: map your strengths to the type of impact you want to drive. If you thrive on deep focus, complex systems, and technical leverage, the IC path can be your force multiplier. If you’re energized by coaching talent, orchestrating outcomes vs output OKRs, and building cross-functional momentum, management might be your best lane. In either path, revisit the decision periodically — careers aren’t one-way doors.

Another thread I appreciated was how she approaches scope and ownership. Whether you’re shipping as an IC or leading as a manager, momentum comes from framing problems tightly, sequencing bets, and reducing operational drag. I often encourage teams to use a simple try do consider framework to prioritize learning loops, and to treat developer evangelism, forward deployed engineers, and founder-led GTM as strategic tools to accelerate product-market fit lessons.

Finally, we turn the page to the most recent chapter — becoming a first-time founder. Amber shared the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon, and her words of wisdom for engineers with interest in starting their own company from 0 to 1 align with my experience: start with a painfully specific problem, tighten feedback cycles, and keep GTM simple before you scale. Early on, zero to one B2B marketing is about credibility, not campaigns; talk to users, ship obvious value, and let your product creator mindset guide the roadmap.

If you’re exploring co-founding dynamics, you can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder

You can follow Amber on Twitter at @amfeng

In sum, whether you identify as an IC, manager, or future founder, the most sustainable careers are portfolio-shaped: evolve your role as your strengths and context change, measure progress by outcomes, and invest in systems that make great work easier to repeat.

October 21, 2025
Executive Hiring That Scales: Battle-Tested Tactics to Find the Right Leaders, Right Now

Executive hiring is one of the highest-leverage — and riskiest — decisions a founder can make. As someone who has scaled product organizations, I’ve learned that the playbook for landing the right leaders changes dramatically as you move from startup to scale. A recent deep dive with Jack Altman, co-founder & CEO of Lattice, crystallized the patterns I see most often: what to prioritize, what to avoid, and how to run a process that consistently produces great executive hires.

The first principle I align with: hire for the next 18-24 months, not the next 5 or 10 years. Early on, the company’s needs shift so fast that long-range “perfect fit” profiles become theoretical at best and paralyzing at worst. I look for leaders who can unlock the next chapter of growth with clear, near-term outcomes — and who have the range to adapt as the strategy evolves. (Here’s the blog post he mentioned about the different stages a CEO faces.)

Founders often get burned by hiring “too big.” Over indexing on BigCo experience or chasing seniority and lofty titles rarely matches the messy, hands-on reality of a startup’s current challenges. I’ve made that mistake — selecting the resume that looked flawless on paper — only to find misalignment on pace, ownership, and scope. Conversely, some of my most impactful leaders started as more junior, undiscovered talent with clear spikes, grit, and coachability. When in doubt, I bias toward the person who shows me how they’ll win here, not just how they won elsewhere.

My end-to-end executive hiring process is intentionally rigorous and replicable. I start by defining the business outcomes we need over the next 18-24 months, then codify them into a scorecard that guides sourcing, interviews, and reference checks. I source via targeted outreach to operators who’ve solved adjacent problems at similarly complex scale. In interviews, I blend behavior-based probes with practical work sessions: “Walk me through how you’d build this team from zero to ten,” “Model the first 90 days,” “Show me the operating rhythms you’ve used to drive outcomes.” I look for crisp thinking, specificity, and an instinct for prioritization under constraints.

References are non-negotiable — and I don’t just confirm facts; I test patterns. I ask backchannels for stories of adversity, the candidate’s default leadership mode under pressure, and how they grew their managers. When stakes are high, I’ll also do references on references to validate consistency. The goal isn’t perfection; it’s reducing variance and surfacing the truth about ownership, resilience, and learning velocity.

There are telltale red flags that an executive lacks an ownership mentality. They blame context rather than diagnose systems. They talk in abstractions without metrics. They focus on headcount before outcomes. They can’t articulate a teachable point of view or how they’d uplevel managers. On the flip side, the strongest candidates connect strategy to execution, quantify trade-offs, and show how they’ll build a high-agency culture from day one.

Most executive hiring errors trace back to fuzzy scope, wishful thinking, or skipping process under time pressure. I guard against this with a 30-60-90 plan tied to measurable leading indicators: decision velocity, operating cadence, pipeline or funnel advancements, hiring throughput and quality bar, and the health of manager layers. If those early signals don’t materialize, I intervene quickly with clarity, coaching, and constraints. And if it still isn’t working, I part ways fast and fairly — the team deserves decisive leadership.

Finally, I’m deliberate about when to promote internally versus hire externally. Internal promotions preserve momentum, culture, and context — especially for IC to manager transition moments — while external hires can inject missing capabilities for new phases of growth (for example, founder-led GTM evolving into a multi-channel motion). I think about the executive team like a portfolio: diversify across experience types, time horizons, and risk profiles. Blend seasoned operators who stabilize systems with high-upside builders who unlock step-changes. That balance is what sustains execution as you scale.

Executive hiring is never “set and forget.” It’s an ongoing discipline of clarifying outcomes, assessing talent against the company’s current chapter, and building the processes that remove luck from the equation. Do that well, and you’ll feel it everywhere: sharper strategy, faster learning loops, and a leadership bench capable of carrying you from startup to scale.

Inspired by this post on First Round.

October 21, 2025
Master Early-Stage Communications: Actionable Lessons from Figma, Uber, and Beyond

Early-stage communication is a product strategy lever, not a press-release afterthought. In my work, I’ve seen the difference a clear narrative makes for founder-led GTM, product discovery, and those early product-market fit lessons that determine whether a company breaks through or stalls. That’s why I was eager to dig into the discipline with someone who’s built communications at category-defining scale.

Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma.

Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden.

Our conversation focuses on what a great communications strategy looks like at early-stage startups. As a product leader, I was struck by how directly the comms fundamentals reinforce core product management leadership behaviors: clarify the customer problem, define the narrative tension, and show proof. She broke down the basics for founders who aren’t familiar with this function, and shared advice for thinking beyond just announcing your Series A funding. I layered on how that same narrative becomes the throughline for zero to one B2B marketing — unifying positioning across product, sales, and customer success.

She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. I connected this to product discovery: the best message testing mirrors the way we validate hypotheses in product — message pillars, audience-specific proof points, and iterative learning sprints that refine what resonates before you scale paid or earned channels.

Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. I add a product-centric lens: do the pre-brief like a roadmap review — align on objectives, anticipate risks, prepare crisp artifacts (message map, data, and customer evidence), and practice bridging so you can protect the narrative under pressure.

We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. My guidance to founders echoes this: hire for strategic clarity first, channel expertise second. In the earliest chapters, a lean, outcomes-focused comms function amplifies founder-led GTM, accelerates learning cycles, and compounds trust with customers, candidates, and investors.

If you treat communications as an extension of product — a disciplined system for discovering, validating, and scaling the narrative — you’ll see compounding returns. That mindset aligns your story with your strategy, makes every launch a proof point, and turns early momentum into durable market position.

Inspired by this post on First Round.

October 21, 2025
Cracking Government Sales: Lessons on Long Cycles, Risk, and Pivoting to Product-Market Fit

Working with public-sector buyers is a different sport than traditional enterprise sales, and I’ve learned that getting it right demands rigor, patience, and empathy. That’s why I was eager to dive into the realities of selling into government with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. The conversation sharpened my own playbooks for B2G sales and underscored how product management leadership must adapt when the buyer is a city, county, or state agency.
We unpacked the practicalities of going to market with government: the extra-long sales cycles, layers of subcontractors, and the need to convince risk-averse decision-makers to take a chance on a startup. In my experience, this requires founder-led GTM early on, paired with meticulous stakeholder mapping, procurement fluency, and airtight compliance. I’ve found it’s crucial to identify the economic buyer, policy owner, legal gatekeeper, and program operator—and then multi-thread relationships so momentum isn’t lost when a champion rotates roles or a budget committee delays.
When cycles stretch into quarters or years, I put a premium on structured pilot design. I aim for time-boxed proofs of value with clear milestones, measurable policy outcomes, and deliverables that de-risk adoption for the agency. This approach aligns incentives for forward progress, while giving the vendor room to iterate on product discovery without jeopardizing trust. It also creates a shared narrative that risk-averse decision-makers can carry into internal approvals.
We also took a step back to traverse the winding road that led to Promise in its current form. Like so many founders I’ve advised, the early journey involved recalibrating the problem-solution fit. Phaedra explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. Her experience mirrors what I watch for in my own teams: leading indicators such as stalled deployments, low utilization by the primary user, misaligned unit economics in government procurement, or policy constraints that cap impact despite strong intent from stakeholders.
From a product-market fit lens, the lesson is to separate mission conviction from mechanism flexibility. Keep the mission constant, but be ruthless about pivoting the mechanism when evidence stacks up. For me, that means codifying hypotheses, setting explicit kill/commit thresholds, and running rapid, qualitative cycles with front-line operators. In the public sector, small usability frictions often become policy blockers—so I test workflows in the field, not just in demos, and pressure-test compliance, data-sharing agreements, and funding sources during discovery, not after.
For founders navigating a pivot, I recommend three disciplined moves: narrow the value proposition to a single, high-frequency pain; re-sequence your GTM around the budget line item that actually funds the work; and redesign onboarding to deliver a visible win inside one reporting cycle. These moves increase the odds of institutional buy-in and compress the time to proof points, even amid long procurement paths.
Ultimately, selling to government rewards clarity, credibility, and outcomes over output. The path is slower, but when you align your roadmap to measurable public impact—and build trust with the program staff who carry the day-to-day load—you create durable, compounding value. That’s where founder-led GTM, rigorous product discovery, and a willingness to pivot converge into true product-market fit lessons for the public sector.

October 21, 2025
How I Build Highly Technical Enterprise Products: Hard-Won Lessons from CockroachDB and Nate Stewart

Building a highly technical enterprise product is as much about disciplined focus as it is about engineering excellence. When the stakes include mission-critical uptime, data integrity, and scale, the product decisions we make today compound for years. That’s why I’m constantly looking for patterns that help my team make fewer, better choices.

Recently, I sat down with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. Our conversation crystallized a number of principles that I’ve seen work in my own practice and that I believe every enterprise product leader should internalize.

First, focus starts with a brutally specific use case. Nate walked through how the Cockroach team narrowed the aperture on where their database would be irreplaceable, not just incrementally better. That clarity anchored the go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. In my experience, this is the hardest muscle to build. I’ve found it helpful to articulate a one-sentence “non-negotiable” use case, followed by a short list of adjacent use cases we’ll explicitly defer.

Second, treat over-commitment as a structural risk. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. I track this debt explicitly: a ledger of promises, effort estimates, and the strategic rationale for each commitment. We cap the total “commitment points” per quarter, require a written business case for any exception, and sunset low-impact promises with transparent communication. This keeps the roadmap credible and prevents well-intentioned deals from silently hijacking strategy.

Design partnerships are the force multiplier in deeply technical categories — especially when working with conservative enterprise clients. Nate outlined different types of design partners and why you should have all of those represented in the early days of your startup. I map partners along two axes: ambition (visionary to conservative) and environment (startup to regulated enterprise). A healthy portfolio includes at least one of each: a visionary who pushes the frontier, a pragmatic mid-market partner who validates repeatability, and a regulated enterprise that stress-tests compliance, security, and operability.

To make design partnerships work, I rely on a simple operating contract: shared problem statement, measurable outcomes, and mutually agreed constraints. We align on exit criteria before we start, time-box pilots, and avoid bespoke code unless it is clearly on the critical path to the broader product-market fit. Executive alignment on both sides and weekly joint reviews keep momentum high and surprise low.

For product leaders stepping into a new role, nothing matters more than building a rock-solid partnership with a CEO as the first head of product. I’ve found three habits indispensable: a shared narrative (why we win), a living strategy doc (how we win), and a predictable cadence (when we decide). I send pre-reads before our 1:1, frame trade-offs in terms of risk and reversibility, and use disagree-and-commit to keep the organization moving. This creates trust, speeds decisions, and shields teams from thrash.

Finally, I’m intentional about how I solicit honest feedback across the executive team. I rotate a “red team” to stress-test critical bets, run brief anonymous pulses after major launches, and host cross-functional postmortems that focus on outcomes vs output. I also schedule regular skip-level interviews to uncover operational friction that might never surface in leadership meetings. These mechanisms create a continuous learning loop without slowing down the business.

In sum, the craft of enterprise product management lives at the intersection of clarity, constraint, and collaboration. Define a use case so sharp it excludes most opportunities. Manage customer promises like a portfolio of risk. Build a diverse, intentional set of design partners. And invest early in executive alignment and feedback channels that scale with your ambitions. That’s how we turn technical excellence into durable enterprise value.

October 21, 2025
From PM to VP: Proven Tactics to Accelerate Your Product Career and Lead with Confidence

I’ve spent my career growing product teams and coaching product managers, and I’m continually drawn to leaders whose playbooks translate across company stages. One standout is Jiaona Zhang (she goes by JZ), whose journey offers an especially clear roadmap for moving from individual contributor to executive product leadership.
JZ is the VP of Product at Webflow. Before that, she was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems. She teaches product at Stanford and mentors rising product leaders. You may also know her for the widely shared article, “Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products).”
What resonates most with me is her framing of the product career path. Instead of a linear ladder, think of three distinct phases: contributing as a PM, managing PMs, and leading the function. I’ve used a similar model to guide my own teams, and I’ll walk through how I apply this framework in practice.
Phase 1 — The PM role: When you’re breaking into product, focus on environments that will compound your learning. I look for signs of strong product discovery, clear ownership of product roadmapping and sprint planning, and a culture that values outcomes vs output. In interviews, I ask how success is measured (OKRs, customer outcomes, adoption) and how PMs partner with engineering and design. Early mistakes are common: trying to own decisions without owning the problem, shipping features without a minimum lovable product mindset, and confusing velocity with value. To avoid these traps, anchor your work in customer problems, link every roadmap item to measurable outcomes, and practice crisp storytelling that connects strategy to execution.
Phase 2 — The managing phase: The IC to manager transition is a shift from doing the work to building the system that does the work. As you become more senior, zoom out from features to portfolios, from experiments to strategy. When hiring, I look for complementary archetypes across the team — the product creator who thrives in zero-to-one, the operator who scales repeatable playbooks, the analyst who brings rigor to prioritization, and the evangelist who aligns stakeholders. For first-time managers, my advice is to establish clear decision rights, define the bar for product quality, and coach toward autonomy. Balance mentoring with mechanisms: weekly product reviews, outcomes-driven OKRs, and lightweight rituals that reinforce clarity without micromanaging.
Phase 3 — The executive phase: At this stage, I treat the product organization itself as a product. Define a vision, clarify the customer (your CEO, exec peers, board, and of course end users), and build feedback loops. With the CEO, align on the narrative, business model bets, and the handful of company-level outcomes that matter most. With peers on the exec team, drive cross-functional planning so GTM, finance, and product are synchronized around impact, not just output. With the board, translate strategy into measurable progress and risk mitigation. The goal is to ship strategy: clear choices, intentional sequencing, and a portfolio that advances product-market fit and durable growth.
Whether you’re trying to break into product, grow into management, or step into the executive arena, this three-phase arc is a reliable compass. Invest in product discovery, tie work to outcomes, and develop the operating cadence that turns intent into impact. That’s how you accelerate from PM to VP — and lead with confidence at every step.

Inspired by this post on First Round.

October 21, 2025