Tag: zero to one B2B marketing

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.

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
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
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
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
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
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
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
Inside Figma’s 5-Phase Community-Led Growth Playbook to Ignite Organic GTM

When I study companies that turn product-market fit into durable, compounding momentum, Figma stands out. In this breakdown, I walk through Figma’s five phases of community-led growth and share how I’d apply each step to build an organic growth engine. My lens is product management leadership paired with pragmatic GTM thinking, so the emphasis is on what to do, when to do it, and why it works.

Phase 1 centers on the lessons from years in stealth mode — specifically, how to start planting the seeds for a community when you don’t have a fully-formed product. I focus on the inflection point to emerge from stealth, what signals matter, and how to use early feedback loops for product discovery without over-rotating on feature requests. Quietly building is necessary; quietly engaging is essential.

In this early phase, my playbook prioritizes rigorous product discovery, crisp problem narratives, and a cadence that makes learning visible. I invest in relationship-building with credible early adopters, share prototypes thoughtfully, and shape outcomes over output through disciplined product roadmapping and sprint planning. The goal is to design a community that feels invited into the creative process while preserving the integrity of your vision.

Phase 2 is all about the launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing. Here, founder-led GTM matters. I pair zero to one B2B marketing with specific audience rituals, leaning into channels where the product can be experienced, not just described. The message avoids enterprise jargon and instead showcases feel, speed, and collaboration, so the community can instantly “get it.”

Phase 3 shifts the focus to activation via community gravity. The goal is to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. This is where I formalize an evangelist strategy — spotlighting workflows, templates, and stories that reduce the cost of the first session. I think about developer evangelism patterns applied to designers: celebrate makers, distribute small wins widely, and build momentum with authentic, peer-to-peer proof.

The final two phases connect passionate individual users to an enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Those choices underscore a disciplined sequencing of PLG with a sales overlay — land with love, expand with proof, monetize with timing.

In practice, this means evolving from bottoms-up adoption to clear value narratives for team and enterprise tiers, while tuning SaaS pricing and packaging to customer maturity. I optimize the handoff from product-led signals to sales motions, align success metrics to outcomes (not just usage), and enable procurement-friendly paths without dulling what made the product magical. That’s the GTM trade-off: protect the community engine while scaling into enterprise.

If you’re building your own community-led growth engine, these phases offer a durable blueprint: learn in stealth, launch where your audience lives, activate with authentic evangelism, and scale with a thoughtful enterprise bridge. Done well, this approach compounds — it strengthens product-market fit, accelerates zero to one B2B marketing, and sets the stage for sustainable growth without overreliance on paid channels.

October 21, 2025