Tag: product-market fit lessons

Go Totally Asynchronous: Inside Sidharth Kakkar’s Remote, Autonomous Culture That Scales

I’ve spent years leading product teams across global B2B SaaS, and few topics spark more debate than building a remote team that operates totally asynchronously. Recently, I revisited the playbook of Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.)

Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management.

Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves.

In this analysis, I dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. I’ll unpack how to share company updates asynchronously every week; advice on how to approach goal-setting and performance feedback while minimizing micromanagement; tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal; thoughts on how to assess asynchronous communication skills when hiring; and how this culture impacts a founder’s role and schedule.

On weekly updates, asynchronous communication shines when it is consistent, structured, and outcomes-focused. I recommend a lightweight cadence that combines a written executive summary, links to artifacts (roadmaps, PRDs, dashboards), and optional short Looms for rich context. Tie each update to outcomes vs output OKRs so teams self-calibrate without meetings, and make updates searchable so new hires can ramp themselves with a clear trail of decisions and tradeoffs.

For goal-setting and performance feedback, autonomy and clarity must coexist. Define clear success metrics upfront, timebox discovery, and use product roadmapping and sprint planning rituals that emphasize measurable customer outcomes over task completion. Replace micromanagement with transparent expectation docs, written performance narratives, and asynchronous 360 feedback—so individuals know what good looks like and can course-correct without waiting for a meeting.

Transparency and documentation are the backbone of a remote, autonomous culture. Centralize decisions in a single source of truth, standardize decision records, and maintain a living discovery log alongside Subscript’s running product/market fit journal. This practice compresses feedback loops, preserves institutional memory, and accelerates product discovery by making assumptions, experiments, and results easy to consume across time zones.

When hiring, I prioritize asynchronous communication skills as first-class selection criteria. Use written work samples, time-boxed take-home prompts, and collaborative docs to evaluate clarity, rigor, and empathy in writing. Look for signal such as strong structuring, crisp problem statements, thoughtful tradeoffs, and proactive documentation of risks and unknowns—capabilities that predict success on distributed teams.

This culture fundamentally reshapes a founder’s role and schedule. With deep work protected and status noise automated, leaders can spend more time on strategy, customer conversations, and coaching. Decision latency drops because context is captured in writing, and the organization scales through principles rather than approvals—exactly what you want in a high-trust, high-leverage product operating system.

There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas.

Inspired by this post on First Round.

October 21, 2025
Airtable’s Journey to Product-Market Fit: Hard-Won Lessons on Building Horizontal Products

I recently dove deep with Andrew Ofstad, co-founder of Airtable, to unpack Airtable’s path to product-market fit and the realities of building a truly horizontal product. As a product leader, I’m always looking for patterns that translate across teams and stages — and this conversation offered a wealth of practical insights for founders and product managers alike.
We started with first principles: how the founders came together, their vision for the product, and what the initial prototypes looked like. That early narrative matters — it anchors positioning, keeps scope disciplined, and ensures your earliest builds reflect the core value proposition rather than a laundry list of features.
From there, we stepped through Airtable’s alpha, beta, and launch timelines, as well as their early traction. I pay close attention to these milestones because they reveal the learning cadence: how quickly teams validated hypotheses, which signals they treated as leading indicators, and how they balanced qualitative pull with quantitative adoption during product discovery.
We also explored the challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building. In my experience, the key is to land a small set of canonical use cases, articulate crisp jobs-to-be-done, and build narrative clarity around the “why now.” Without this, even great products struggle to convert curiosity into active usage.
On commercialization, we dug into how to approach pricing and competition, as well as their early go-to-market strategy. For products with broad applicability, I’ve found that founder-led GTM is essential early on — it shortens the learning loop and informs SaaS pricing and packaging. Start with simple, customer-aligned tiers, validate willingness to pay against clear outcomes, and keep positioning focused on value, not feature parity.
We then looked ahead to what the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision. Scaling a horizontal product requires tight product roadmapping and sprint planning, strong messaging discipline, and an unwavering commitment to the core value — all while layering ecosystem leverage, templates, and community to accelerate adoption without diluting the product’s identity.
Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear. My takeaway: great horizontal products find product-market fit by starting narrow in use case, obsessing over teachability, and letting customer outcomes pull the roadmap forward.

Inspired by this post on First Round.

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
Founder-Led Customer Success: My Proven Playbook for NRR, Feedback Loops, and First CS Hires

I’m constantly looking for battle-tested ways to operationalize founder-led customer success in B2B SaaS. In that spirit, I recently dug deep into the patterns that have powered Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision.

Founder-led customer success is one of the most overlooked levers in early company building, yet it’s often the fastest path to durable retention, sharper product-market fit, and a more effective founder-led GTM. When I roll up my sleeves with founders, I focus on building tight feedback loops, defining accountability for net revenue retention, and sequencing the first customer success hire with intention.

How to structure early customer check-ins, plus a framework to help surface more specific feedback. In practice, I run these as short, recurring sessions for the first 60–90 days, anchored on outcomes, not features. I use a simple cadence and agenda: confirm the customer’s jobs-to-be-done and success criteria, inspect friction along the critical path, quantify value moments, and close with two commitments (one for us, one for the customer). To elicit specificity, I lean on prompts like: “Walk me through the last time you used this,” “What almost made you stop?” and “What has to be true to consider this indispensable in 90 days?”

The most impactful questions that founders and customer success managers should ask all their customers. My shortlist includes: What outcome did you hire us to achieve, and how will you measure it? What’s the single biggest blocker between you and that outcome right now? Which part of our product experience feels surprisingly valuable—and which feels like work? If this tool disappeared tomorrow, what would you do instead? What needs to happen for you to expand usage with confidence in the next quarter? These questions turn qualitative check-ins into quantifiable insight that sharpens product discovery and reduces churn risk.

Why everyone at the company owns the net revenue retention metric — not just the customer success function. I treat NRR as a company-wide operating metric, not a department KPI. Product owns value creation and time-to-value; Sales owns expansion hygiene and deal quality; Marketing owns ideal customer profile clarity and expectation setting; Finance and RevOps instrument leading indicators like activation rate, feature adoption, and health scores. When we wire NRR into planning and OKRs across teams, we translate customer signals into roadmap priorities and revenue outcomes without handoffs getting lost.

How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp. The ideal early CS leader is a builder-operator: consultative, technically fluent, comfortable in ambiguity, and obsessed with outcomes. I design interviews around live exercises—diagnose a customer scenario, map a 90-day success plan, and instrument a health score with leading and lagging indicators. For compensation, I favor a base/variable split with a meaningful portion tied to net revenue retention and adoption milestones, plus early equity to align with long-term value creation. This profile accelerates learning loops between customers, product, and go-to-market.

The throughline across all of this is simple: founders who lead from the front on customer success compress the learning cycle that drives retention and efficient growth. By formalizing early check-ins, asking high-signal questions, making NRR a company sport, and hiring a builder for that first CS role, we turn customer conversations into a strategic engine for product management leadership and sustainable expansion.

Inspired by this post on First Round.

October 21, 2025
Scaling Your Co-Founder Relationship: Rituals, Decision Rights, and Trust Lessons from Labelbox

I’ve learned that a startup’s trajectory often mirrors the strength of its co-founder relationship. With that lens, I sat down to unpack how to scale trust, decision-making, and speed between co-founders as the company itself scales. Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, I take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We traced how Manu and Brian came together as co-founders and landed on the idea for Labelbox. That origin story matters: it reveals the early signals of shared conviction, complementary experience, and a clear problem thesis—foundations I look for when evaluating co-founder fit in any startup. Before writing a line of code, they intentionally aligned their skillsets, values and responsibilities. I emphasize this step in my own product management leadership practice: make the invisible explicit. Define roles, boundaries, and how decisions get made while the stakes are low, so you can move fast when the stakes are high. As the company grows, their rituals for spending valuable time together keep the relationship durable. They use thought-starter questions for deep discussions and even benefit from sharing an executive coach. I’ve seen this playbook consistently reduce friction: structured prompts surface misalignments early, while an external coach creates a safe container to reset, recommit, and keep momentum. We also dug into how they run the executive team at scale and sketch out decision rights. Clear decision rights accelerate execution, prevent rework, and protect the co-founders’ relationship from getting pulled into every operational knot. In my experience, codifying who decides, who contributes, and how dissent is handled is one of the fastest ways to boost operating cadence without sacrificing trust. Manu and Brian both offer practical advice to other founders—whether you’re in the early stages of looking for a co-founder or aiming to add a little magic to an existing partnership. If you’re building, apply their lessons: align on values early, institutionalize rituals, use an executive coach, and be explicit about decision rights. These are the simple, scalable mechanisms that preserve focus, speed, and resilience as you pursue product-market fit and scale your executive team. You can follow Manu at @manuaero and Brian at @RiegerB on Twitter.

October 21, 2025
Rethinking Quitting: Annie Duke’s Decision Science for Smarter Product Strategy

I recently sat down with Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” Her latest work, “Quit: The Power of Knowing When to Walk Away,” offers a provocative lens on one of the most misunderstood skills in product management and startup leadership: the decision to stop.
In our world, quitting is often dismissed as failure. We celebrate grit, persistence, and the legendary founders who “just kept going.” But in my experience leading product strategy, I’ve learned that knowing when to walk away is frequently the hallmark of great judgment. Annie’s perspective reframes quitting as a strategic move that preserves focus, accelerates learning, and ultimately improves outcomes.
What struck me most is how our psychology conspires against sound walk-away decisions. We’re vulnerable to sunk cost fallacy, status quo bias, and identity-driven attachment to our bets. As product teams, that shows up as clinging to features that don’t move the needle, extending pilots that never convert, or chasing a go-to-market motion that looked good in a deck but stalls in reality.
“Quit: The Power of Knowing When to Walk Away” argues that quitting, done right, is not capitulation—it’s optimization. I see that play out in product discovery and portfolio management. The teams that outperform define clear kill criteria up front, tie decisions to leading indicators rather than vanity metrics, and treat each initiative as a reversible bet until product-market fit evidence says otherwise.
Practically, I’ve found a few tactics echo Annie’s approach: set timeboxed experiments with explicit stop-loss rules; pre-commit to thresholds that trigger a review; and separate decision rights so the person advocating for a project isn’t the sole decider on its continuation. Decision logs, red-team reviews, and base-rate comparisons help strip away narrative bias and keep us grounded in outcomes vs output OKRs.
Annie also offers guidance for advice-givers—those moments when you need to nudge a teammate or founder to change course. Lead with curiosity, not combat. Ask, “If we were starting from zero today, would we choose this strategy?” Frame quitting as a path to the original goal, not a retreat from it. And when necessary, be gentle, yet firm—clarity is kind.
For product leaders, the real unlock is weaving quitting into the operating system. Stage funding for initiatives, escalate the evidence bar as you invest more, and normalize regular “stop, pivot, or double-down” checkpoints. This keeps resources flowing to the highest-leverage bets and reduces the emotional tax on hard calls.
If you’re rethinking your roadmap, pipeline, or GTM motions, this is the moment to institutionalize better walk-away decisions. Align quit criteria to business outcomes, define decision cadence, and coach teams to see quitting as learning in action. It’s how you create velocity toward product-market fit while minimizing opportunity cost.
If this resonates, add “Quit: The Power of Knowing When to Walk Away” to your reading list. And if you want to keep up with the ideas behind decision science and strategic quitting, you can follow Annie on Twitter at @AnnieDuke.
Quitting isn’t the opposite of perseverance—it’s how we preserve our best bets. When we treat walking away as a disciplined product management capability, we build stronger strategies, ship better products, and protect the most precious asset we have: time.

Inspired by this post on First Round.

October 21, 2025
Finding Product-Market Fit Twice: Alma’s bold pivot and tactics to stay close to customers

Finding product-market fit is hard enough once; doing it twice is the rare pressure test that separates resilient product teams from the rest. As a product leader, I’m obsessed with how teams navigate pivots without losing sight of their users — and Alma’s journey is a masterclass in staying customer-obsessed while scaling.

In a recent conversation with Harry Ritter, I dug into how disciplined product discovery, clear decision-making, and founder-led GTM can accelerate learning cycles. Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices.

What stands out to me is that the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities. That’s an enormous shift in operating model, unit economics, provider experience, and buyer expectations — yet the throughline was a relentless focus on customer needs and outcomes.

Team building matters even more during moments like these. Approaching team building as a solo founder means deliberately constructing complementary skills around the founder’s strengths and gaps. I look for three early anchors: an execution-first product partner, a zero-to-one GTM lead who can validate demand with founder energy, and a metrics-driven operator to keep the system healthy as complexity scales. Values, operating cadence, and decision rights must be explicit, or a pivot will expose the cracks.

Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on is a powerful way to de-bias signal. I’ve used this clinical-style approach — open-ended history, precise symptom probing, differential hypotheses, and a closing summary for confirmation — to improve customer interview quality. It transforms conversations from anecdote collection into consistent, comparable product data you can act on.

When the ground shifts, rallying your team through a pivot depends on clarity and cadence. I anchor on a simple narrative: why the environment changed, what we’ve learned from customers, where we’re going, and how we’ll measure progress. Staying competitor aware — not competitor obsessed keeps speed and focus on the user, while avoiding reactive roadmaps. And it’s crucial to internalize The difference between building a marketplace versus a platform. Marketplaces require liquidity, trust, and incentive design; platforms demand extensibility, APIs, and ecosystem health. Confusing the two leads to misaligned KPIs and misallocated resources.

My practical playbook for a “second PMF” includes: weekly founder-led customer calls until patterns converge; a structured interview template and central repository; a pivot memo with explicit kill criteria and success metrics; a liquidity or engagement model depending on whether you’re a marketplace or platform; and a tight KPI set (retention, activation, and quality-of-service indicators) to validate product-market fit beyond growth vanity metrics.

Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here. The Alma story reinforces a timeless truth: proximity to customers is the ultimate unfair advantage — in discovery, in execution, and especially in moments of change.

You can follow Harry on Twitter at @harryritter1.

Inspired by this post on First Round.

October 21, 2025
How Retool Hit $2M ARR Pre‑Launch: My Playbook on Developer Focus, Product‑Market Fit, and GTM

I spend my days building and scaling B2B products, and Retool’s journey to $2M in ARR before launch is a masterclass in focus. It’s also a case study I revisit when coaching teams on developer evangelism and founder-led GTM.

Listening to David Hsu recount the early decisions made the strategy crisp: stay laser‑focused on developers, remove the boilerplate of internal tools, and earn trust with speed.

Retool, a low-code platform for developers building custom internal tools.

Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform.

Early on, plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. I’ve heard variations of this skepticism whenever a team doubles down on a specific persona—especially developers.

What struck me is the clarity around the target customer and the discipline to pursue language-market fit. When you get the words right for developers—their jobs-to-be-done, primitives, and constraints—you lower friction across product discovery, onboarding, and activation.

Equally instructive is how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and the way the team prioritized creating incredibly tight feedback cycles with these early evangelists. That’s founder-led GTM at its best: sit with users, ship fast, instrument everything, and turn customer conversations into a roadmap.

On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. I’ve lived those bumps, too; they’re signals to tighten the loop, not reasons to pivot away from your core user.

My takeaways for product leaders: start with developer empathy, not feature breadth. Use founder bandwidth to run high-frequency user sessions, shadow internal tool builds, and test copy until you hit language-market fit. Treat docs, templates, and examples as part of the product; they often outperform UI tweaks for time-to-value.

Operationally, stand up a lightweight, metrics-driven pipeline that connects discovery to delivery. I like a weekly cadence that pairs qualitative insights with activation, time-to-first-value, and expansion signals—classic product-market fit lessons that prevent local optimizations. When you see pull, lean into developer evangelism and zero to one B2B marketing, not paid acquisition.

If I were replicating this playbook today, I’d deploy a small, forward-deployed team to embed with design partners, capture real workflows, and ship improvements daily. Pair that with clear outcomes vs output OKRs so the team optimizes for customer outcomes, not just shipping velocity. That’s how you earn trust with developers and translate it into durable ARR.

Retool’s story reinforces a principle I teach often: conviction in the right user beats broad appeal every time. Focus wins, feedback compounds, and the market rewards teams that can turn skepticism into traction—especially when the users are developers.

October 21, 2025
Defeat Inertia: A Product Leader’s Playbook to Lower Barriers and 10X Adoption

Change is the job. I build and sell products to reshape behaviors and markets, yet I’m constantly reminded that change is hard. Going back to chemistry, catalysts don’t just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. That framing has reshaped how I approach product strategy, go-to-market, and adoption.

One lens I return to is “The Catalyst: How to Change Anyone’s Mind.” It underscores a simple truth: the obstacle isn’t always the idea; it’s the friction around it. The book outlines 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence. I’ve found that when we diagnose which barrier is in the way, our product and GTM decisions get sharper, faster, and far more effective.

Do you really need a 10X better product? Sometimes yes—but not always. In practice, the biggest competitor I face isn’t another vendor; it’s inertia. Prospects cling to the status quo because switching feels risky, expensive, or cognitively heavy. My job is to make staying put feel riskier than moving forward. That means de-risking the decision, shrinking the perceived switching cost, and removing “homeostasis hooks” like entrenched workflows and sunk costs. When I design onboarding, migration tooling, and progressive rollouts, adoption climbs—even when the product advantage is 2–3X, not 10X.

Urgency matters, but pressure backfires. I aim for urgency that respects autonomy. Instead of “buy now or else,” I show windows of compounding value—why acting this quarter creates momentum, unlocks ROI, or secures outcomes that are harder to capture later. Time-bound pilots, seasonal use cases, or milestone-based pricing can motivate action without triggering reactance. The goal is momentum, not manipulation.

Freemium isn’t just for software. I apply the same principle—reduce uncertainty and upfront commitment—to physical products and services through pilots, limited-scope deployments, try-before-you-buy programs, refundable deposits, warranties, and modular packaging. The point is to let customers experience value with minimal friction. If it lowers uncertainty and builds confidence, it belongs in your arsenal.

On pricing and negotiation, I default to clarity, not concessions. I anchor on measurable outcomes, map tiers to value ladders, and use give-get rules so price changes are tied to scope or risk, not arbitrary discounts. This avoids signaling lower quality and keeps identity intact—buyers want to feel like smart stewards, not bargain hunters. Framing around business impact (“Here’s the cost of staying put versus the ROI of switching”) consistently outperforms feature recitations.

Identity and category creation are powerful accelerants. When a prospect feels an offer threatens who they are—or what team norms demand—adoption stalls. I reframe the story so the decision aligns with their identity (“modern operator,” “data-driven leader”) and, when needed, I redefine the category to reduce comparison shopping. If you’re a new category, you’re not asking buyers to replace an incumbent—you’re inviting them to adopt a better lens. That shift diffuses reactance and opens the door to new budgets and metrics.

Corroborating evidence matters most when stakes are high. I equip champions with proof that speaks to their peers: credible case studies, ROI models, third-party benchmarks, and pragmatic references. Multiple independent signals—especially from customers “like them”—shorten the distance between interest and commitment. I’ve seen adoption jump when we pair a hands-on pilot with peer validation at each gate.

Here’s the throughline I use with teams: don’t push harder—remove friction. Diagnose which barrier in REDUCE is at play, then pick a targeted tactic: restore agency to counter reactance, offset endowment with easy reversibility and migration, bridge distance with progressive steps, shrink uncertainty with trials and proof, and stack corroborating evidence at the right moments. When we build products and GTM motions around lowering these barriers, we don’t just sell better—we make change feel inevitable.

Inspired by this post on First Round.

October 21, 2025
Inside X1’s Pivot: The Playbook Behind a 600K Waitlist and a $15 Million Raise

I gravitate toward consumer fintech stories that show how product-market fit is earned through conviction, narrative, and execution. In that spirit, I dug into the journey of Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation. The arc of this build is a masterclass in pivoting under pressure and orchestrating a high-velocity launch without losing sight of fundamentals.

Just last week, X1 announced a $15 million funding round. To understand how they got here, I rewound the tape and focused on the pivotal decisions that transformed uncertainty into momentum.

First, the human side of the pivot: “The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product.” I’ve been through moments like this, and the lesson is consistent — you can’t cling to sunk costs when the world changes. Teams need psychological safety to grieve the old plan, and leadership must reframe the mission quickly so energy channels into discovery, not denial.

Second, the demand-side proof: “How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything.” This is a powerful consumer move. Before a single line of code defines the product, the market should be able to tell you — via signups and sentiment — whether your story resonates. In practice, that means sharpening positioning, crafting a memorable name and visual identity, and pressure-testing the value prop across landing pages, press briefs, and social. Treat the narrative as an MVP.

Third, the launch mechanics: “The launch strategy that crashed X1’s website and built up a 600K long waitlist.” When a launch overpowers your infrastructure, it’s both a win and a wake-up call. The playbook here blends scarcity (invites, phased access), social proof (credible press, testimonials), and a tight referral loop that rewards participation. In my experience, the secret is sequencing: tease, announce, then escalate with proof points — all while instrumenting analytics, scaling infrastructure, and staffing support for the surge.

Finally, the strategic lens: “Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times.” Consumer PMF hinges on emotion and habit, not just utility; you measure it through retention curves, organic growth engines (word of mouth, referrals), and depth of engagement. For fundraising in tough markets, the bar is higher: show authentic demand (waitlist-to-activation conversion), defensible economics (unit economics, risk controls), and a credible path to moats (brand, data, network effects). Narrative clarity matters — investors respond when your story, metrics, and roadmap triangulate.

Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here. My takeaway: lead with story, validate with signal, operationalize for scale, and keep the team emotionally aligned through the change. That’s how you turn a pivot into a product-market fit flywheel.

You can follow Deepak on Twitter at @drao1.

October 21, 2025
Nail Your Founder-Led Sales Pitch: My Proven Playbook to Build Rapport, Validate Narrative, and Win

Building is comforting; selling is confronting. I’ve lived both realities, and I coach founders through this transition every week. The moment you leave the quiet sanctuary of product discovery and step into founder-led GTM, everything gets noisier—buyers, budgets, and objections all collide. That’s precisely why a crisp, testable sales narrative matters as much as your MVP.

When I need to re-center on first principles, I often recommend “Founding Sales: The Early Stage Go-to-Market Handbook.” It’s a practical touchstone for zero to one B2B marketing and a great companion as you stress-test your early motion. What follows is the playbook I use to get a founder-led sales pitch into ship-shape—fast.

First, build your selling muscles with deliberate practice. I use a lightweight daily regimen: 10 targeted outbound touches, two discovery calls, and a 15-minute retro where I review call recordings and tighten my talk-to-listen ratio. I timebox every section of the call—agenda, discovery, narrative, proof, and next step—so I can diagnose exactly where I’m losing altitude. The goal is compound learning, not one-off heroics.

Next, try the “turbo rapport” challenge. In the first 60–90 seconds, find an authentic point of human connection that’s relevant to the business problem. Mirror the customer’s language, confirm their goals, and demonstrate that you’ve done the homework on their context. This isn’t small talk; it’s the foundation for high-fidelity discovery and a more truthful read on product-market fit.

Then, self-diagnose your selling narrative with five hard questions: 1) Do I articulate the customer’s problem crisply in their words? 2) Do I quantify the cost of the status quo? 3) Do I present a differentiated approach that’s easy to verify? 4) Do I offer credible proof (customer evidence, metrics, or a quick pilot)? 5) Do I secure a concrete next step tied to value realization? If any answer is shaky, the narrative—not just the delivery—needs work.

If you’re creating a new category (and trying to create a new budget), the bar is higher. Anchor on the economics of change: identify the trigger events that make the problem urgent, quantify the value unlocked, and pre-negotiate where budget can reallocate from (sunset tools, process inefficiencies, or adjacent line items). Provide a one-slide business case and a time-bound pilot so stakeholders can say “yes” without political risk. This is product management leadership in the wild.

For inspiration, I often point to the playbooks used building Atrium: instrument your process with activity and outcome metrics, run tightly scoped pilots to surface early leading indicators, and codify a crisp one-page narrative that any seller (including you) can deliver consistently. Treat every call as a mini-experiment and adjust the message weekly based on data, not vibes.

Don’t overlook the power of building a customer advisory board. Hand-select design partners who feel the pain viscerally, and co-develop the narrative with them. Their language becomes your message; their metrics become your proof. This closes the loop between discovery and go-to-market and accelerates signal on what resonates.

Finally, operationalize feedback. Tag call snippets by objection type, correlate deal progression with talk tracks, and track conversion by segment to learn where the pitch truly lands. Founder-led GTM thrives on short learning cycles: ship a narrative, measure outcomes, refine, repeat. Do this for four to six weeks and your pitch won’t just feel tighter—it will convert.

The shift from building to selling is supposed to feel uncomfortable. Lean into it with structure, heart, and discipline, and you’ll turn early chaos into a repeatable motion. That’s how you earn the right to scale.

October 21, 2025
Hard‑Won M&A Playbook: Lessons from Daniel Debow on Selling Three Startups

Founders often ask me how to navigate startup acquisitions without losing focus on product, customers, and culture. I view M&A as an extension of product strategy: it’s about creating long-term value, not just closing a deal. That’s why I study practitioners who’ve done it repeatedly and well—and few have a clearer track record than Daniel Debow.

I draw on insights from Daniel Debow, a VP of Product for Demand at Shopify. Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007.

From my vantage point leading product teams, Daniel’s journey underscores a core truth: the moving parts of an M&A process as a startup demand the same rigor we apply to product discovery and go-to-market execution. When I’m advising founders, I concentrate on aligning strategy, timing, and relationships so the outcome—whether you sell now or later—remains squarely in your control.

First, I assess conditions at potential acquirers with the same discipline I’d use to qualify enterprise customers. I look for executive sponsorship, a clear product adjacency, an integration path (org and technical), and real ownership of outcomes post-close. If I don’t see resourcing commitments, aligned incentives, or a P&L that will house the asset, I assume the environment won’t be “founder-friendly.” On the flip side, established companies that want to be more founder-friendly should make the sponsor and decision-maker map explicit, publish their integration playbook, define success metrics early, and commit to retaining key builders.

Next, I differentiate between clear buying signals and the companies that are just “tire kicking.” Buying signals include rapid access to senior decision-makers, diligent technical and security deep-dives, direct discussions about deal structure and integration, and proactive work on a joint customer narrative. Anti-signals include vague interest without a timeline, refusal to share org charts or decision rights, and perpetual “one more meeting” cycles led only by corp dev. When signal strength drops, I reset expectations or pause the process to protect the team’s focus.

Relationships make or break outcomes, so I build meaningful relationships with executives of all types, not just corp dev teams. I cultivate trust with the GM who owns the P&L, the product and engineering leaders who will operate the asset, the sales leader who needs a story customers will buy, and the finance lead who models the upside. I share roadmaps, customer win stories, and integration hypotheses, then ask for honest pushback. This turns diligence into joint problem-solving and sets the tone for post-acquisition execution.

Finally, I’m deliberate about techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team. With investors, I align on valuation guardrails, role clarity in negotiations, and information sharing protocols. Internally, I limit the circle early, establish a single source of truth (a lightweight data room and weekly update), and script what we’ll tell managers if rumors surface. If and when a deal becomes likely, I plan retention, customer communication, and integration milestones concurrently so momentum carries through day one.

The through line in all of this: treat M&A like a high-stakes product launch. Validate intent, qualify the buyer, insist on ownership of outcomes, and protect your team’s energy. Drawing on Daniel’s example, you can structure an acquisition process that preserves optionality, increases deal quality, and—most importantly—sets you up to scale the impact of what you’ve built.

Inspired by this post on First Round.

October 21, 2025