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Engineering Leadership That Scales: Strategy, Velocity, and Org Design from Carta, Stripe, Uber, Calm
Read more: Engineering Leadership That Scales: Strategy, Velocity, and Org Design from Carta, Stripe, Uber, CalmHigh-growth engineering orgs succeed by pairing a clear strategy with compounding platform bets and outcome-focused execution. In this deep dive, I break down practical patterns I use: how to write principles that drive decisions, structure strategy docs that translate into action, and measure velocity with DORA and SPACE. I share a nuanced approach to policy…
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Inside Bard’s Playbook: How to Ship AI Fast, Build Ethically, and Outlearn Competitors
Read more: Inside Bard’s Playbook: How to Ship AI Fast, Build Ethically, and Outlearn CompetitorsBuilding AI products demands speed and responsibility. I unpack the Bard blueprint—how principled constraints, early public learning, and tight product theses enable rapid iteration without sacrificing ethics or trust. You’ll learn why live context and modality matter, how to set launch thresholds for LLM features, and where grounding and UX often beat sheer model size.…
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Winning with Open Source and SaaS: My GTM Playbook, Monetization Tactics, and Founder Fit
Read more: Winning with Open Source and SaaS: My GTM Playbook, Monetization Tactics, and Founder FitOpen source and SaaS can thrive together when community trust, product design, and go-to-market are orchestrated as one system. In this reflection, I break down lessons on monetizing open source, using developer evangelism for category creation, and sequencing founder-led GTM. You’ll see why consumption-based pricing and enterprise-grade features unlock scalable revenue. I also highlight how…
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Master Modern Entrepreneurship: Build Lean, Start Young, and Obsess Over Customers
Read more: Master Modern Entrepreneurship: Build Lean, Start Young, and Obsess Over CustomersModern entrepreneurship rewards teams that learn faster than the market shifts. In this first-person playbook, I share how to build lean, start young with disciplined experiments, and obsess over customer discovery to drive product-market fit. I unpack why many startups stumble, how to correct common misreads of Lean Startup and MVPs, and how founders can…
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The New PLG Playbook: Avoid the Trap, Win Enterprise, and Break the $10B Ceiling
Read more: The New PLG Playbook: Avoid the Trap, Win Enterprise, and Break the $10B CeilingProduct-led growth can stall when user value doesn’t translate into enterprise outcomes. In this first-person playbook, I show how to avoid the PLG trap by aligning value to executive OKRs, cultivating champions, and operationalizing the seed, land, and expand framework. I explain why Dropbox had almost no company value and unpack why Dropbox is worth…
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From Zero to One: My Playbook for Building a World‑Class Sales Org (Lessons from Figma)
Read more: From Zero to One: My Playbook for Building a World‑Class Sales Org (Lessons from Figma)Building a world-class sales org starts long before headcount—it starts with clarity. In this first-person playbook, I share how I assess readiness for a sales function, choose the right first hire, and integrate them to amplify learning across product and go-to-market. You’ll learn how to transition from founder-led sales, shape an early sales motion, and…
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From Vertical Focus to Power Users: My Playbook for Product-Market Fit and Founder Mindset
Read more: From Vertical Focus to Power Users: My Playbook for Product-Market Fit and Founder MindsetI share a practical playbook for achieving product-market fit by focusing on a tight vertical, building with a community of power users, and making faster, evidence-based decisions. You’ll learn how to design for time-to-first-value, use sprints to reduce work-in-progress, and measure outcomes over output. I also unpack how founder psychology shapes strategy and how frameworks…
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The Human Side of Engineering Leadership: Practical Plays to Build Creative, High-Performing Teams
Read more: The Human Side of Engineering Leadership: Practical Plays to Build Creative, High-Performing TeamsEngineering leadership thrives when clarity, trust, and maker time meet operational excellence. In this first-person playbook, I share how to protect deep work, ship at scale, and align product, design, and engineering around outcomes. You’ll learn practical tactics to curb micromanagement, foster healthy debate, and make declarative decisions that unlock autonomy. I also break down…
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Customer Success Masterclass: How I Design, Build, and Scale a World‑Class CS Org
Read more: Customer Success Masterclass: How I Design, Build, and Scale a World‑Class CS OrgCustomer success is an engine for growth, not an afterthought. In this masterclass, I share how I formalize CS at the earliest stages, the hiring sequence that avoids common fail-cases, and the metrics and rituals that drive outcomes vs output. You’ll learn how I decide who owns renewals, where CS fits in the org, and…
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How to Find Your Product Wedge: Battle‑Tested SMB SaaS Lessons from Square, Gusto, and My Playbook
Read more: How to Find Your Product Wedge: Battle‑Tested SMB SaaS Lessons from Square, Gusto, and My PlaybookFinding a product wedge is the fastest path to product‑market fit in SMB SaaS. In this first‑person playbook, I unpack how companies like Square and Gusto use form‑fitting solutions to win early, then expand horizontally with discipline. You’ll learn when to choose vertical versus horizontal strategies, how to apply The Three Horizons Model, and why…
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The Secret Lever Behind Replit’s Hypergrowth—and the Product Playbook You Can Reuse
Read more: The Secret Lever Behind Replit’s Hypergrowth—and the Product Playbook You Can ReuseI break down how Replit turned a frictionless coding experience into a compounding distribution engine—and why that’s the secret lever product leaders can reuse. My take covers AI’s impact on the “software creator” role, the lessons behind early fundraising setbacks and near YC rejections, and a monetization strategy that prices depth, not curiosity. You’ll learn…
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Scaling Enterprise AI That Sells: Battle-Tested Playbooks for PMF, Champions, and Agentic AI
Read more: Scaling Enterprise AI That Sells: Battle-Tested Playbooks for PMF, Champions, and Agentic AIScaling enterprise AI takes more than a great demo—it demands trust, governance, and measurable outcomes. I share battle-tested playbooks on finding champions, structuring pilots for ROI in under 30 days, and building full-stack generative AI systems that are dependable under load. You’ll learn telltale signs of true product-market fit, how to scale LLMs with guardrails…
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