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Go Totally Asynchronous: Inside Sidharth Kakkar’s Remote, Autonomous Culture That Scales
Read more: Go Totally Asynchronous: Inside Sidharth Kakkar’s Remote, Autonomous Culture That ScalesI break down how Sidharth Kakkar built Subscript as a fully asynchronous, remote, and autonomous organization—and what product leaders can apply today. You’ll learn how to run weekly company updates without meetings, set goals and deliver performance feedback while avoiding micromanagement, and scale transparency through documentation. I also cover hiring for asynchronous communication skills and…
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Operations vs Algorithms: How I Scale Startups with Data Science, Team Design, and Pre-Mortems
Read more: Operations vs Algorithms: How I Scale Startups with Data Science, Team Design, and Pre-MortemsOperational grit can power the early innings, but long-term advantage comes from data science that scales your best learnings. Drawing on insights from Ian Wong—co-founder and CTO of Opendoor and formerly Square’s first data scientist—I share a practical blueprint for moving from operations-heavy to algorithm-driven. Learn how to hire the right early data scientists, design…
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Airtable’s Journey to Product-Market Fit: Hard-Won Lessons on Building Horizontal Products
Read more: Airtable’s Journey to Product-Market Fit: Hard-Won Lessons on Building Horizontal ProductsIn this first-person breakdown, I explore Airtable’s path to product-market fit with co-founder Andrew Ofstad and extract lessons every product leader can apply. We walk through early prototypes, alpha/beta/launch milestones, and the signals that defined early traction. I dig into how horizontal products find their wedge, refine positioning, and turn curiosity into active usage. We…
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Inside Figma’s 5-Phase Community-Led Growth Playbook to Ignite Organic GTM
Read more: Inside Figma’s 5-Phase Community-Led Growth Playbook to Ignite Organic GTMI break down Figma’s five phases of community-led growth and translate them into an actionable blueprint for startups. You’ll see how to seed a community in stealth, when to emerge, and how to launch where your audience actually lives. I show how to drive trials without forcing immediate switching and how to build an evangelist…
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From Roadmaps to Sprints: Proven Tactics to Ship Software at Scale Without Chaos
Read more: From Roadmaps to Sprints: Proven Tactics to Ship Software at Scale Without ChaosIn this deep dive, I share a playbook for going from product roadmapping to sprint planning without chaos, drawing on insights from a conversation with Retool’s engineering leadership. Learn how to balance consumer vs. enterprise trade-offs, and who belongs in the room to represent product, engineering and design. See how the “try, do, consider” framework…
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My Playbook for the First 10 Hires: Lessons from Steven Bartel on Gem & Dropbox
Read more: My Playbook for the First 10 Hires: Lessons from Steven Bartel on Gem & DropboxEarly-stage hiring is make-or-break, especially when your startup has zero brand recognition or recruiting support. In this first-person breakdown, I share lessons from Steven Bartel, co-founder and CEO of Gem, whose Dropbox experience spans analytics, Dropbox Paper, and hiring during a 25-to-1500 person scale-up. You’ll learn a practical trick for sourcing second-degree network connections, how…
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Founder-Led Customer Success: My Proven Playbook for NRR, Feedback Loops, and First CS Hires
Read more: Founder-Led Customer Success: My Proven Playbook for NRR, Feedback Loops, and First CS HiresFounder-led customer success is a powerful lever for early-stage SaaS growth. Drawing on lessons from Catalyst and InVision, I share how I structure early customer check-ins, the questions that generate high-signal feedback, and why net revenue retention must be owned across the company. I also outline the ideal profile for your first CS hire, how…
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Scaling Your Co-Founder Relationship: Rituals, Decision Rights, and Trust Lessons from Labelbox
Read more: Scaling Your Co-Founder Relationship: Rituals, Decision Rights, and Trust Lessons from LabelboxHow do you scale trust, clarity, and speed between co-founders as your startup takes off? In this first-person breakdown, I explore how Manu Sharma and Brian Rieger of Labelbox aligned skills and values before code, built durable rituals, and shared an executive coach to stay in sync. You’ll learn practical ways to define decision rights…
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Rethinking Quitting: Annie Duke’s Decision Science for Smarter Product Strategy
Read more: Rethinking Quitting: Annie Duke’s Decision Science for Smarter Product StrategyQuitting has a branding problem in startup culture, but Annie Duke’s decision science flips the script. I share how “Quit: The Power of Knowing When to Walk Away” maps directly to product management—using kill criteria, timeboxed experiments, and evidence-driven reviews to avoid sunk costs. You’ll learn practical tactics to reduce bias, coach teams through hard…
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Finding Product-Market Fit Twice: Alma’s bold pivot and tactics to stay close to customers
Read more: Finding Product-Market Fit Twice: Alma’s bold pivot and tactics to stay close to customersFinding product-market fit twice is a rare challenge — and Alma’s pivot offers a blueprint for doing it well. I break down how disciplined customer discovery, structured interviews, and founder-led GTM created signal through uncertainty. You’ll learn how to rally a team through change, stay competitor aware without becoming obsessed, and distinguish marketplace dynamics from…
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Enterprise Messaging Secrets for Startups: Lessons I Took from Salesforce and Twilio
Read more: Enterprise Messaging Secrets for Startups: Lessons I Took from Salesforce and TwilioStartups often underinvest in corporate messaging, but the right narrative can align product, marketing, and sales to accelerate growth. Drawing on lessons from Salesforce and Twilio, I outline how to craft a company-level promise, define durable value pillars, and prove impact with customer outcomes. Treat messaging as a living system: test, measure, and iterate as…
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Engineer Your GTM: Actionable Architecture, Refactoring, and Pricing Lessons from Rich Rao
Read more: Engineer Your GTM: Actionable Architecture, Refactoring, and Pricing Lessons from Rich RaoI approach go-to-market like an engineer: start with an architecture method, instrument the system, and refactor deliberately. Rich Rao’s path across Meta and Google underscores why a blueprint beats ad-hoc tactics, especially in zero to one B2B marketing. Key takeaways include ditching unfocused free trials, aligning pricing with value metrics, and scheduling GTM refactoring sprints…
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