Tag: zero to one B2B marketing

Enterprise Messaging Secrets for Startups: Lessons I Took from Salesforce and Twilio

I’m relentlessly focused on how enterprise-grade marketing translates into startup advantage—and how product and go-to-market stay in lockstep as companies scale. I connected with Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. Her journey offers a pragmatic blueprint for building a corporate message that actually drives pipeline, product adoption, and long-term category leadership.
Early-stage teams often over-rotate on launch tactics and underinvest in the corporate narrative. The fix starts with discipline: define the problem you exist to solve, articulate a company-level promise (not just features), anchor it with three or four durable value pillars, and reinforce it with specific proof—customers, outcomes, and metrics. As I’ve seen firsthand, this narrative becomes the backbone for founder-led GTM, product roadmaps, and sales enablement, ensuring every touchpoint—from the homepage to the pitch deck—tells the same story.
What stands out in Sara’s approach is the enterprise rigor behind message development. She takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. That evolution is essential: your Series A message should feel sharper and more outcome-driven than your seed-stage one, and by growth stage, your story should clearly connect product capabilities to business value and category design.
From a product management leadership perspective, I treat messaging as a living system. I instrument it with win/loss insights, run message tests in demand gen and on key sales calls, and feed the learning loop back into positioning and the roadmap. When the message resonates, you’ll see shorter sales cycles, tighter ICP focus, and cleaner handoffs from marketing to sales to customer success. When it doesn’t, it’s a signal to refine who you serve, the problems you prioritize, or the value proof points you bring forward.
For marketers eyeing the CMO seat, one capability rises above the rest: commercial empathy. Build joint accountability with sales around pipeline quality and revenue, not just MQL volume. Establish regular, data-driven reviews where both teams refine ICP, test the narrative, and agree on proof customers. Most importantly, learn how to form collaborative, not combative relationships with sales counterparts. That partnership is how great messaging becomes a repeatable GTM motion.
If you want to continue learning from leaders who’ve built category-defining narratives, you can follow Sara on Twitter at @SaraVarniBright. Use her enterprise playbook as scaffolding, then adapt it to your stage: keep the story simple, outcome-oriented, and relentlessly customer-backed—and let your product and sales motions amplify it in unison.

October 21, 2025
Engineer Your GTM: Actionable Architecture, Refactoring, and Pricing Lessons from Rich Rao

I approach go-to-market like an engineer: define the system, design the interfaces, and be willing to refactor. Reflecting on lessons from Rich Rao affirmed that a rigorous, architecture-first mindset can turn messy GTM motions into a scalable operating system for product-led growth and B2B marketing.

Rich Rao is the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals.

In our discussion, he explains how his engineering background influences his approach to GTM — from an architecture method to the concept of refactoring. That frame resonates deeply with how I run product management leadership at scale: start with the blueprint, then iterate deliberately instead of stacking one-off tactics.

We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. That story captures the zero to one B2B marketing muscle: when constraints are high, the “system design” of GTM matters more than any single channel.

There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons. I’ve seen the same pattern: open-ended free trials often attract the wrong segments, inflate support load, and mask weak activation. Time-boxed or usage-capped trials tied to a clear value metric perform better, reduce churn, and sharpen SaaS pricing strategy.

Here’s how I operationalize an engineering lens in GTM. First, I create an “architecture method” for distribution: define system boundaries (ICP, jobs-to-be-done), interfaces (hand-offs between marketing, sales, and product), and SLAs (lead response, onboarding, success). Second, I instrument everything to observe bottlenecks — then “refactor” GTM like code: remove dead channels, simplify packaging, and standardize the path to value. Third, I treat pricing as part of the design, not a late-stage patch: align paywalls with activation moments, use value-based metrics, and avoid feature sprawl that confuses buyers.

When we need step changes, I run scheduled refactoring sprints: prune legacy offers, consolidate SKUs, and clarify messaging to reduce cognitive load. Just as technical debt slows product delivery, GTM debt (too many plans, inconsistent positioning, orphaned channels) drags conversion and expansion. A quarterly cadence to pay down this debt keeps the system healthy.

The outcome is a repeatable motion: an engineered go-to-market system that compounds learning, supports product-market fit lessons, and scales across segments without breaking. If you lead product or growth, think like an architect, measure like an engineer, and refactor before your funnel stalls — your team, customers, and P&L will feel the difference.

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
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
Why Communications Deserves a Seat on the Exec Team: Hard‑Won Lessons from Square

Communications isn’t a PR afterthought — it’s a strategic lever that shapes product perception, credibility, and go-to-market outcomes. When I look at the companies that out-execute their peers, they elevate comms to the executive level, align it tightly with product strategy, and treat it as a system — internal and external — not a series of press moments. That’s the lens I brought to a deep dive on startup communications with one of the sharpest operators in the field.

After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley’s School of Law, Aaron now runs Background Partners, a communications consulting firm.

In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on:

Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. I’ve seen comms drive strategic clarity across product, GTM, and people operations — and when it reports into the CEO alongside product and revenue, you get tighter narratives and faster decisions. Early-stage founders often think an agency will manufacture momentum; in reality, founder-led storytelling, disciplined messaging, and consistent execution are far more effective (and cost-efficient) than outsourcing too early.

The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. In the zero-to-one phase, comms should align the company around a sharp narrative, build trust with early users and talent, and reduce confusion in the market. Media coverage can be a credibility accelerant, but it’s rarely a dependable pipeline channel. Treat it like air cover for your product-led or founder-led GTM, not a replacement for it.

A 3-question framework for simplifying your company message early on. The most resilient narratives fit on a single slide and answer three things crisply: What problem do we solve? Why now? Why us? I map this directly to product positioning and roadmap priorities so every launch, customer story, and executive communication reinforces the same core promise.

How to prep for interviews and deal with difficult lines of questioning. Great media training looks a lot like great product reviews: anticipate the hard questions, practice concise answers, and bridge back to your core message without dodging. I keep a living Q&A doc, run red-team drills with my staff, and record mock interviews to tighten delivery, tone, and body language. When challenged, acknowledge, answer, and anchor — it earns credibility.

How to think about commenting on events in the news, or message layoffs to the team. Not every headline requires your voice; when you do comment, ensure it’s authentic, relevant to your mission, and aligned with your stakeholders. For sensitive internal communications — especially layoffs — specificity, empathy, and accountability matter most. Explain the why, the what, and the what’s next, and ensure managers are equipped to support their teams in real time.

Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen. The explosion of owned channels, the speed of social, and the blurring of internal and external narratives mean your messaging framework must be simple, repeatable, and durable across audiences — customers, candidates, investors, and employees.

We also recommend checking out his two excellent Medium posts:

–What’s Your Hour in ‘Silicon Valley Time’?

No, you don’t need to hire an agency

You can follow Aaron on Twitter at @zamosta.

Inspired by this post on First Round.

October 21, 2025
Decentralized Community Masterclass: Bottom‑Up Growth, Creator Partnerships, First Hires

I recently sat down with Ben Lang, Head of Community at Notion, to unpack how a decentralized, bottom‑up community can power durable, compounding growth. In my day-to-day leading product, I’ve seen community-led growth move markets—hearing the detailed playbook behind it brought the strategy into sharp focus for operators and founders alike.

Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today.

But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees.

In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on: Tackling community organically from the bottom-up, and why you shouldn’t go top-down; What companies are best suited to a centralized vs. decentralized community approach; Partnering with YouTubers and other creators; His advice to founders on finding your own first community hire.

Here’s my biggest takeaway on the bottom-up vs. top-down decision: bottom-up wins trust before it asks for anything. When you enable passionate users to teach, build, and share—then get out of their way—you unlock authentic advocacy that no paid campaign can replicate. Practically, this looks like community-led onboarding (templates, live office hours, and user-run meetups), lightweight governance (clear brand and safety guardrails), and a creator toolkit (assets, sample briefs, and success stories) that fuels developer evangelism and product discovery without stifling creativity.

On centralized vs. decentralized approaches, fit matters. Centralized communities shine when your product is compliance-heavy, your ICP requires curated expertise, or you need consistent, high-signal feedback loops. Decentralized communities thrive when your value compounds through remixing and sharing—think modular templates, integrations, and a vibrant ecosystem of product creators. My operating rule: start centralized for quality and learning, then progressively decentralize as playbooks harden and local leaders emerge. Instrument the handoff with clear roles, lightweight certifications, and community health metrics (activation, contribution velocity, and sentiment).

Creator partnerships—especially with YouTubers and niche educators—act as force multipliers. Treat creators like product partners, not channels: co-develop curricula, share early product roadmaps where appropriate, and equip them with data-backed talking points and reusable assets. Build a transparent value exchange (rev share, affiliate programs, early feature access), define success upfront (reach, engagement, and downstream activation), and keep content evergreen with updates tied to releases. The result is a repeatable growth loop that blends PLG, social proof, and zero to one B2B marketing.

For founders hiring the first community leader, optimize for a builder-operator hybrid: someone who has shipped programs, written docs, hosted events, and can close the loop from insight to iteration. Look for evidence of creator empathy, editorial judgment, lightweight product instincts, and the ability to scale through systems (templates, playbooks, and tooling). Define outcomes, not activities: measure community-led pipeline, activation lift, retention improvements, and the velocity of high-quality user feedback feeding product management leadership.

The throughline is simple: community is a product. Design it with the same rigor—clear ICPs, onboarding, retention hooks, and feedback loops—and it becomes a durable moat. Whether you lean centralized or decentralized, start bottom-up, enable your best users, and let creators help you tell the story the market actually wants to hear.

October 21, 2025
From Doubt to Dominance: Vanta’s Bold Bet on Startup Security and Product-Market Fit

I’m drawn to product stories where conviction outruns consensus, and few examples illustrate that better than Christina Cacioppo and the journey behind Vanta. As a product leader, I pay close attention to the early decisions that compound into category leadership, especially in B2B SaaS and founder-led GTM.

Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).

After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s.

But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea.

From a product-market fit standpoint, this is a masterclass in sensing a rising constraint before it becomes urgent. Betting early on SOC-2 compliance for startups signaled a strong thesis about where the market was headed and created a durable wedge into startup security. That’s the kind of proactive product discovery and strategic foresight I try to instill in teams.

It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice.

Founder-led sales often bridge the gap between problem insight and market traction. Watching this arc—from zero selling experience to big-time enterprise deals—reinforces a truth I’ve seen repeatedly: intimate problem ownership beats polished sales scripts in the early innings.

She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A.

These choices map to a disciplined product management playbook: prioritize trust and outcomes, validate retention before scaling top-of-funnel, and use cash flow break-even to preserve strategic optionality. In practice, that’s how you earn leverage with both customers and capital—and it’s a powerful way to de-risk growth while accelerating product-market fit.

If you’re building in B2B SaaS, the takeaways are clear: anticipate regulatory and buyer shifts, compound credibility with early lighthouse customers, encourage word-of-mouth growth by over-delivering on the core job-to-be-done, and let fundraising serve the strategy—not define it. In my experience, this is how category winners are made.

October 21, 2025
Build a High‑Velocity PLG Growth Engine: Measurable Tactics from Notion and Slack

I gravitate toward conversations that blend analytical rigor with genuine customer empathy. In my role leading product, I’m constantly looking for repeatable ways to operationalize product-led growth and transform word-of-mouth into measurable business outcomes. That’s why I was eager to study how Notion approaches growth in practice, and what I learned aligns closely with the systems we build to scale sustainable, metrics-driven growth.
Rachel Hepworth, Head of Marketing at Notion.
Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily.
Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers.
Here’s how I translate those lessons into a practical, product-led growth playbook you can put to work.
First, high-speed feedback cycles are non-negotiable. In a PLG environment, learning velocity compounds. I instrument experiments end-to-end (from top-of-funnel through activation and retention), ship in small batches, and review impact daily. Rapid iteration across acquisition creatives, onboarding flows, and in-product prompts turns anecdote into evidence and evidence into compounding gains. The flywheel is simple: ship, measure, learn, repeat—faster than your competitors.
Second, identify early indicators of which sign-ups are most likely to convert to paid customers. I score intent using a blend of source quality, setup depth, activation milestones, and collaboration signals. Think about actions like completing a core “aha” workflow, inviting teammates, or integrating with a critical tool—these leading indicators help forecast conversion far better than lagging metrics. With this in place, you can route high-intent cohorts into tailored onboarding, sales-assist, or customer education paths that lift conversion and retention.
Third, evolve your top-of-funnel metrics as the product and motion mature. Early on, breadth matters—optimize for qualified traffic and net-new sign-ups. As the engine matures, shift your focus to quality and efficiency: channel mix, activation rate, cost to acquire activated users, and downstream expansion signals. I treat metrics like a portfolio—retire vanity metrics, promote predictive ones, and ensure each KPI ladders to revenue, not just reach.
Finally, clarify how marketing, product, and sales co-own the funnel in a PLG company. Marketing leads demand generation, channel orchestration, and education that primes users for success. Product owns activation, in-product conversion, and expansion mechanics that turn usage into habit and habit into revenue. Sales (often sales-assist) engages where complexity, security, or procurement require a human touch. When each function owns a distinct stage—and the handoffs are instrumented—the go-to-market strategy becomes both scalable and measurable.
The throughline is simple: build a growth marketing engine that respects customer love and word-of-mouth while holding the bar on measurement. With fast feedback loops, predictive intent models, evolving top-of-funnel metrics, and crisp cross-functional ownership, product-led growth stops being a slogan and starts becoming your operating system.

October 21, 2025
Mastering Product-Market Fit with the REV Model: My Battle-Tested Category Playbook

Product-market fit is measurable — and the REV (revenue, engagement and value) model is one of the most practical ways I’ve found to quantify it while aligning product, go-to-market, and category strategy.

I’m continually inspired by how Artem Kroupenev, VP of Strategy at Augury, operationalized this thinking to scale a new category. Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing.

Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in. Those lessons map closely to how I build and scale products today.

Here’s how I translate these ideas into a practical playbook you can apply right now: Augury’s storyboard-based approach to product vision, how to sell to a limited pool of customers, the REV (revenue, engagement and value) model for measuring product-market fit, and when founders should start exploring creating a new category to operate in.

Augury’s storyboard-based approach to product vision resonates with how I align teams and customers. I start with narrative storyboards that depict the current pain, the first “magic moment,” and the end-to-end value realization. These storyboards become a shared contract between product, sales, and customers — clarifying what must be true for adoption and value. They also drive ruthless prioritization: if a feature doesn’t move a storyboard frame closer to value realization, it waits.

When the market has a limited pool of customers, precision matters more than volume. I’ve found success by sequencing accounts into tight cohorts, running deep discovery with forward-deployed product teams, and setting explicit learning goals per cohort. Lighthouse wins matter, but only if they’re repeatable — so I anchor early deals to a clear “who/what/why” ideal customer profile and instrument the entire journey from pilot to expansion to prove repeatability.

The REV (revenue, engagement and value) model gives me a crisp, triangulated view of product-market fit. Revenue shows willingness to pay and expand (e.g., pilot-to-paid conversion, logo retention, net revenue retention). Engagement reveals product stickiness (depth, frequency, and breadth of usage; time-to-first-value; activation and expansion milestones). Value proves that outcomes are real (business impact metrics tied to the customer’s objectives, such as cost savings, yield improvement, or risk reduction). I don’t rely on a single metric; I set threshold targets for each dimension by cohort and track deltas over time to see whether the product is getting easier to sell, faster to adopt, and more valuable to customers.

I also treat REV as a lifecycle score. Early on, I’m comfortable with weaker revenue signals if engagement and value are strong and accelerating — that’s a prompt to invest in packaging, pricing, and sales enablement. Later, if revenue is strong but engagement lags, I pause new segments and sharpen onboarding, “aha” moments, and workflows until usage curves show healthy compounding. The point is to let each dimension guide the next set of investments.

On category creation, timing is everything. I only lean in when evidence shows the existing labels constrain the value story, the product reliably produces unique outcomes, and customers start using our language organically. That’s the moment to name the problem space, codify proof (case studies and benchmarks), rally an ecosystem, and publish a crisp narrative that explains what’s new, why it matters now, and how success is measured. Attempt it too early and you confuse buyers; do it once REV signals are strong, and you accelerate market pull.

If you’re leading in industrial manufacturing or building hardware–AI–SaaS solutions, these principles are especially vital: storyboard the vision to align complex stakeholders, sell with intent to a limited customer pool, and instrument the REV score to prove outcomes at every stage. Even in pure SaaS, the same playbook applies — the mechanics are different, but the signals of fit are universal.

My challenge to your team: within two weeks, storyboard your core value journey, define three to five REV metrics per lifecycle stage, and review them by cohort. You’ll not only see where product-market fit truly stands, but you’ll also know exactly what to do next — whether that’s sharpening onboarding, revisiting packaging, or laying the groundwork for a category you can own.

October 21, 2025
How a 3-Time Founding Team at Pilot Unlocked Product-Market Fit Faster—My Proven Playbook

I’m often asked how elite teams compress the journey to product-market fit. One story I keep returning to is Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. For the past six years, she’s built Pilot alongside her two co-founders, Waseem Daher and Jeff Arnold — and what makes this trio extraordinary is that they’ve stuck together across three startups.

As repeat founders, the team learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. Yet there were mistakes that prevented those products from becoming an outsized success. From a product management leadership perspective, I see a clear evolution in how they approached problem selection, product discovery, and go-to-market.

With Pilot, they prioritized picking an acute problem and a huge market to tackle. That simple but rigorous reframing matters: identify a customer segment with a painful, high-frequency workflow; quantify the market; and ensure a compelling “why now.” This is classic founder-led GTM discipline and the essence of practical product-market fit lessons.

They also embraced a deliberately tedious build process for v1: looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them. In my experience, this “do the job, then automate” approach functions like forward deployed engineers for founders — embed with the real workflow, capture edge cases, then translate that knowledge into the system of record.

Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. That willingness-to-pay signal, coupled with pull-based requests for adjacent capabilities, is exactly what I look for before scaling zero to one B2B marketing or hiring beyond the founding team.

My playbook from this story is straightforward: choose a narrowly defined, acute pain in a massive category; run founder-led discovery inside the customer’s workflow; ship code alongside the service until the workflow is reliable; price early to validate value; and align outcomes vs output OKRs so the team optimizes for customer impact, not feature volume. Do this, and you convert messy service learnings into a repeatable product engine.

Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you. For product creators, that choice — and the discipline to live in the customer’s workflow early — is the difference between meandering and momentum.

October 21, 2025
Open-Source GTM Masterclass: Pricing, Packaging, and Paywalls with Grafana Labs’ COO

I sat down with Douglas Hanna, Chief Operating Officer at Grafana Labs. Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization.
Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model.
In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company. That focus on disciplined go-to-market execution resonates with my own experience building product-led motions that respect the community while establishing clear, sustainable paths to revenue.
We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing: I found these principles especially actionable for open source monetization, SaaS pricing, and zero to one B2B marketing.
“When to commercialize a feature vs. switch to a hosted version of a product” — In practice, I look for telltale signals: features that impose heavy operational burden (security, scale, multi-tenant reliability), generate significant infrastructure or support costs, or require advanced governance. That’s when a hosted version can deliver outsized value. For individual features inside the core, I favor commercialization only when the value metric is unambiguous and the user experience remains seamless for the community. The key is a clear migration path from self-managed to hosted, with pricing aligned to usage or outcomes.
“Tried and tested frameworks for pricing and packaging” — I anchor on a few staples: value metrics that correlate with customer outcomes, willingness-to-pay testing, and the 3C lens (customer, competition, company). For packaging, a tiered “good/better/best” model helps segment needs, while usage-based or consumption pricing can unlock elasticity for developer-led adoption. I’ve seen price fences (SSO, RBAC, advanced analytics, scale limits) work well when they map to enterprise readiness rather than core functionality.
“How Grafana Labs thinks about what to put behind a paywall” — I share the same philosophy: keep community-loved, foundational capabilities open to preserve trust and growth, and place enterprise-grade scale, compliance, and governance behind the paywall. This often includes SSO/SAML, audit logs, granular access controls, advanced alerting, longer retention, and premium SLAs. The litmus test is whether the paywalled capability primarily serves larger teams’ risk, reliability, and control requirements.
“How the GTM team was built over time” — The sequencing matters. Early on, lean into product-led growth with strong developer evangelism, documentation, and onboarding. As adoption accelerates, add sales-assist, solutions engineering, and forward deployed engineers to convert complex use cases. Over time, layer in customer success, pricing operations, and ecosystem partnerships. Hiring profiles evolve from generalists to specialists, but the connective tissue remains a tight loop between product, community, and revenue.
Throughout our discussion, I appreciated the rigor in tying pricing and packaging decisions to measurable value, while safeguarding the open-core experience. That balance is the difference between short-term monetization and durable category leadership in observability.
You can follow Douglas on Twitter at @douglashanna.
If you’re building or scaling an open-source business, these GTM patterns provide a pragmatic blueprint: lead with community, monetize enterprise needs, and align pricing to real-world usage. It’s a playbook that rewards trust, clarity, and iteration — and it’s one I’ve seen drive repeatable growth when executed with discipline.

October 21, 2025