Tag: founder-led GTM

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
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.”

Inspired by this post on First Round.

October 21, 2025
How I Hire the Right Marketer at the Right Time: A Proven, High-Impact Startup Playbook

I’m often asked how to hire the right marketer at the right time for a startup. In my role, I take a magnifying glass to the core components of a startup’s marketing org and share a practical playbook you can apply today to reduce hiring risk and accelerate impact.

I start by breaking down the three pillars of marketing roles — product, brand, and growth. Understanding which pillar you need first is a function of your stage, strategy, and the specific gaps on your team.

I explain the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. For example, if founder-led GTM is working but messaging is inconsistent across deals, prioritize product marketing; if awareness stalls and the story doesn’t travel, invest in brand; if sign-ups outpace activation or conversion, it’s time for growth.

Next, I pull back the curtain on how I architect interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. For product marketing, I look for crisp problem framing, narrative craft, and enablement chops; for brand, taste plus discipline in category design and communications; for growth, rigorous experiment design, data fluency, and full-funnel thinking.

I also reflect on what it takes to be one of the earliest marketing hires at a fast-growing company. In the first couple of years, the mandate is to build the marketing org to keep up with the shifting needs of the growing startup—moving from zero to one, to repeatability, to scale—without losing the builder mentality or your bias for outcomes.

For product leaders, founders, and hiring managers, this is a must-read if you’re trying to pluck out the best and the brightest to join your org. The nuances of startup marketing are easy to miss until you’ve lived them; my goal is to translate those lessons into clear signals and repeatable processes you can use.

Use this guide to diagnose where you are, time your next hire, and design an interview loop that reveals real signal. When you align the right marketer with the right moment, you accelerate product-market fit, uplevel cross-functional execution, and create durable growth.

Inspired by this post on First Round.

October 21, 2025
Build a Hybrid Go-To-Market Engine: Hard-Won Lessons from Confluent, Dropbox & Atlassian

I’ve long admired Giancarlo ‘GC’ Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and that functional breadth across standout B2B companies resonates with my own approach to product management leadership.

In this deep-dive, I make the case for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth. I’ve seen this blend unlock efficient, scalable growth without sacrificing enterprise-grade rigor — especially when you’re balancing self-serve and sales-assisted motions before and after product-market fit.

I start by mining lessons from GC’s time at Atlassian and Dropbox, comparing their business models and translating what it takes to make a multi-product go-to-market motion work. For me, the critical levers include crisp segmentation, clear packaging, intentional cross-sell paths, and an obsessive focus on the end-to-end customer journey.

From there, I share my advice for a hybrid approach, including my litmus tests for picking the right metrics and the structure of my weekly meetings. I distinguish inputs from outcomes, leading indicators from lagging indicators, and align each metric to a specific stage of the funnel with a single accountable owner. My weekly operating cadence ties product-led growth health (acquisition, activation, conversion, monetization) to sales pipeline, forecast accuracy, and deal health so both motions reinforce one another.

I also sink tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision. That means pairing qualitative insights with product analytics, instrumenting key aha moments, and documenting friction so the team can remove blockers in priority order. The result is a shared, visual narrative that turns strategy into execution.

On pricing, packaging, and activation, I lean on a few battle-tested principles: anchor pricing to customer value, keep the pricing metric intuitive, right-size tiers for clear upgrade paths, and design first-session experiences to reduce time-to-value. In SaaS pricing, even small tweaks to entitlements, limits, and paywalls can meaningfully shift activation and expansion, so I validate with experiments before rolling changes broadly.

To holistically evaluate any go-to-market strategy, I apply a simple diagnostic framework that scores acquisition, activation, monetization, expansion, and retention, then layers in organizational alignment and operating cadence. This clarity exposes whether issues are strategy, execution, or enablement problems — and where a hybrid model can create compounding gains.

Finally, I focus on team building for a hybrid go-to-market strategy — from hiring profiles to team structure. I look for product builders who can speak revenue, growth leaders who respect product quality, and sales partners who embrace product-led signals. A shared dashboard, a single planning calendar, and joint post-mortems keep incentives aligned.

If you’re a founder, or part of the broader community of founders, product and go-to-market leaders, you’ll find this playbook packed with examples of specific impactful experiments I’ve run, metrics that did or didn’t work out, and common traps that I see teams falling into. The goal is simple: create a durable growth engine that compounds by uniting product-led growth and enterprise selling.

Inspired by this post on First Round.

October 21, 2025
From Founder to CEO: Executive Coach Alisa Cohn on Candid 360 Feedback and Growth

I recently dug into a powerful conversation with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week, and it’s a timely playbook for anyone navigating the shift from founder to CEO.

What resonated most with me is how central self-awareness is to startup leadership—and how hard it is for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa highlights both the right questions to ask and how to get at the root of what people are actually saying in their feedback. In my own practice leading product management, I’ve learned that a multi-source feedback loop is non-negotiable if you want to grow faster than your company’s complexity.

To invite real candor, I set clear expectations up front, guarantee anonymity when appropriate, and ask for specific examples. Prompts I rely on include: What should I start, stop, and continue? When have I been most and least effective? What’s one behavior that would most improve my impact? I also ask for a confidence rating and context (e.g., cross-functional vs. team settings), which surfaces patterns that one-off comments miss. This simple structure keeps feedback actionable for product management leadership and founder-led GTM environments where speed can mask weak signals.

Of course, the hardest part is what to do with what you hear. Not every piece of feedback is useful, and Alisa’s guidance aligns with my own rubric: look for themes across sources, weigh input by proximity to the work and blast radius, separate facts from feelings, and test changes through small, time-boxed experiments. I operationalize changes in my day-to-day routine with calendar nudges, pre-commitments (e.g., publish decision criteria before important calls), and a trusted peer who can observe and nudge me in real time. Small, consistent behavior changes compound faster than sporadic big swings.

We also surface the most common opportunities for growth that show up again and again: communication and decision-making. I’ve seen how a CEO’s personality is unconsciously reflected in the company culture—pace, rigor, appetite for risk, how we treat “no,” and whether we bias toward outcomes vs output. To counter the “shadow of the leader,” I make these drivers explicit: write down decision guardrails, publish decision logs, and define what “good” looks like for communication quality and speed across functions.

Another area we dig into is how to have effective conversations about layering and letting people go. Layering—bringing in experienced leaders above early high performers—works when expectations are clear, roles are well-scoped, and dignity is preserved throughout. My playbook: share the business rationale, define success metrics and timelines, offer a growth path where possible, and avoid ambiguity that erodes trust. When exits are necessary, clarity, compassion, and speed protect both people and culture.

Finally, I’ve adopted a brief reflection ritual that Alisa recommends every founder incorporate into their daily routine. Mine takes ten minutes at day’s end: What mattered most today? What did I learn? What will I do differently tomorrow? This lightweight cadence keeps me honest about progress, especially in the messy middle of the IC to manager transition and the broader journey from scrappy founder to established CEO. It’s also a lifesaver for leaders who struggle to give away their Legos.

You can follow Alisa on Twitter at @AlisaCohn.

Inspired by this post on First Round.

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