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From Prototype to the Pentagon: My Playbook for Winning DoD Customers and Mission Fit
Read more: From Prototype to the Pentagon: My Playbook for Winning DoD Customers and Mission FitWinning customers inside the Department of Defense demands a different playbook than commercial SaaS. In this first-person guide, I share how I achieve mission solution fit, map complex buyer pathways, and align demos to acquisition milestones. You’ll learn how to build trust through forward deployed engineers, avoid common accreditation and integration traps, and craft a…
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Inside Figma’s Product Playbook: Taste, Simplicity, and Storytelling for Extraordinary PMs
Read more: Inside Figma’s Product Playbook: Taste, Simplicity, and Storytelling for Extraordinary PMsDiscover how Figma weaves taste, simplicity, and storytelling into a repeatable product playbook. I break down practical patterns for going from zero to one, prioritizing with conviction, and expanding into multi-product without losing coherence. You’ll learn how to hire and deploy the right talent for “0 to 1” versus “1 to 10,” and how to…
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Inside dbt Labs’ $4.2B ascent: category creation, open source, and monetization playbook
Read more: Inside dbt Labs’ $4.2B ascent: category creation, open source, and monetization playbookThis is a candid product leader’s breakdown of how dbt Labs went from three free-tool users in 2016 to 30,000+ enterprise users and a $4.2B valuation. I unpack the consulting-to-software pivot, the open-source philosophy, and the community-led strategies that made the category inevitable. You’ll learn how to time fundraising only when “things started to break,”…
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Inside Clay’s $1.25B Playbook: Unconventional GTM, Pricing Strategy, and Enterprise Wins
Read more: Inside Clay’s $1.25B Playbook: Unconventional GTM, Pricing Strategy, and Enterprise WinsClay’s $1.25B valuation was earned through a disciplined blend of product-led growth and enterprise rigor. I break down how scrappy community-led tactics, reverse demos, and a self-serve engine fueled early adoption. Credit-based pricing—and rejecting the usage-based model—made value predictable for buyers while preserving upgrade paths. A big bet on content and brand shortened cycles and…
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Just Now Possible Preview: How Real Teams Ship AI—Workflows, RAG, Agents, Evaluation
Read more: Just Now Possible Preview: How Real Teams Ship AI—Workflows, RAG, Agents, EvaluationGet a behind-the-scenes preview of Just Now Possible, a show that goes deep on how real teams ship AI features. I share practical stories about product discovery, gen AI for product prototyping, and evaluation strategies that drive outcomes—not just output. You’ll hear how teams use workflows, agents, and RAG to solve customer problems and evolve…
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Building AI Products That Work: My Playbook for LLM Strategy, Evals, and Orchestration
Read more: Building AI Products That Work: My Playbook for LLM Strategy, Evals, and OrchestrationAI products don’t win on clever prompts—they win on orchestration, observability, and repeatable outcomes. In this first-person breakdown, I share how I design LLM features with prompt decomposition, layered evals, and rigorous risk mitigation. You’ll learn why “thumbs up/thumbs down” won’t cut it, how to log traces for reliable debugging, and when to choose AI…
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From Disruption to Breakthrough: How Stack Overflow’s AI Pivot Became a Product Playbook
Read more: From Disruption to Breakthrough: How Stack Overflow’s AI Pivot Became a Product PlaybookGenerative AI rewrote the developer playbook overnight—and Stack Overflow’s response is a masterclass in product management leadership. Ellen Brandenburger’s team rapidly prototyped conversational search across four iterations, prioritized attribution and transparency for developer trust, and used simple SME-driven scorecards to measure accuracy, relevance, and completeness. When the product didn’t meet the bar, they sunset it—then…
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Mastering AI Evals: Real-World Discovery Tactics to Ship Quality, Safe, Reliable AI
Read more: Mastering AI Evals: Real-World Discovery Tactics to Ship Quality, Safe, Reliable AIClever prompts don’t guarantee reliable AI—evals do. In this first-person recap, I outline how to use golden datasets, synthetic data, and real-world traces to measure what matters. You’ll learn when to choose code-based checks versus LLM-as-judge, how discovery sharpens evaluation, and why criteria drift makes continuous maintenance essential. I also share how to tie evals…
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Inside Braze’s Blitz to $500M CARR: Bold PM Lessons on Going Global and Outsmarting Rivals
Read more: Inside Braze’s Blitz to $500M CARR: Bold PM Lessons on Going Global and Outsmarting RivalsBraze’s sprint to $500M in CARR offers a masterclass in product management leadership, mobile-first strategy, and category creation. I unpack how early insights, a TechCrunch Hackathon origin, and disciplined platform bets turned 1,000 beta signups into 2,200+ paying customers. You’ll learn why “terminal value” product market fit matters, how to “fish in every pond” without…
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How Guideline Rewired 401(k)s: First‑Principles Strategy, Gusto Edge, and Product Wins
Read more: How Guideline Rewired 401(k)s: First‑Principles Strategy, Gusto Edge, and Product WinsGuideline’s approach to modernizing 401(k)s offers a blueprint for product leaders tackling regulated, legacy markets. By building from first principles, integrating deeply with payroll partners like Gusto, and prioritizing transparent pricing and auto-enrollment, the team drove real outcomes and trust. Hitting $120 million in ARR by June 2024 validates the strategy and the execution discipline…
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What Makes or Breaks Executive Hires: My Lessons on Fit, Red Flags, and Measuring Success
Read more: What Makes or Breaks Executive Hires: My Lessons on Fit, Red Flags, and Measuring SuccessExecutive hiring is a make-or-break decision that demands clarity on fit, scope, and measurable outcomes. In this deep dive with Eeke de Milliano, I unpack the ‘buy or build a leader’ decision, common red flags in executive hiring, and how to instrument success early. You’ll hear practical tactics for leadership transitions, stakeholder alignment, and avoiding…
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Scrappy Outbound to ‘Hyperbolic’ PMF: How a COVID Pivot Fueled Owner’s Explosive Growth
Read more: Scrappy Outbound to ‘Hyperbolic’ PMF: How a COVID Pivot Fueled Owner’s Explosive GrowthOwner’s rise from near-zero runway to a $33M Series B is a blueprint for customer-obsessed execution. I unpack how scrappy outbound, embedded discovery with small businesses, and a decisive COVID pivot unlocked “hyperbolic” product-market fit. You’ll see what actually worked to acquire customers, why a measured move to multi-product matters, and how to balance sales-led…
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