October 2025
- AI Strategy (317)
- Generative AI (106)
- IT Leadership (33)
- Leadership (76)
- Product Management (344)
- Product Management Leadership (308)
- Uncategorized (32)
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Scaling With Heart: Self-Aware Leadership, Tough Calls, and 10x Team Performance
Scaling an organization starts with scaling yourself. In this first-person reflection, I share how I build self-awareness, have hard conversations with empathy, and separate hiring errors…
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My playbook: Intuition vs data, big swings, and product-led growth lessons from Slack
Decision-making in product isn’t binary. I outline when to trust intuition versus data, how to manage pace against accuracy, and how to balance big swings with…
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Hard-Earned Lessons from Loom: Product Strategy, Alignment at Scale, and Hiring That Wins
I break down how Loom’s operating system illustrates best-practice product management, alignment at scale, and cross-functional performance that moves the needle. You’ll learn how to use…
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From Zero to One in B2B Marketing: My Proven SaaS Playbook for Growth, Hiring, and Attribution
Going from zero to one in B2B marketing demands focus, founder-led GTM, and rapid learning. I break down how to start early-stage SaaS marketing, allocate resources…
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Supercharge Your Engineering Org: Alignment, AI, and Productivity from Adobe to Etsy
Engineering speed is a function of alignment, not heroics. In this first-person breakdown, I unpack how modern engineering teams can scale productivity with outcomes vs output…
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Building Products in a Post-LLM World: Hard-Won Lessons, Skeptic Busters, and Team Playbooks
I break down how to build products in a post-LLM world with a pragmatic playbook you can put to work immediately. You’ll learn how Sprig’s journey…
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Inside Rewind AI’s Playbook: PMF Breakthroughs, Bold Twitter Fundraise, and the Future of AI
I explore Rewind AI’s path to product-market fit, the cultural habits that enable fast validation, and the bold Twitter-first fundraising strategy that rallied users and capital.…
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From Founder-Led GTM to Repeatable Product-Market Fit
A practical system for turning founder-won deals into a narrow ICP, measurable customer value, and a go-to-market motion others can run.
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Open-Source Commercialization: A Developer-Led Playbook
A practical framework for deciding what stays open, what customers pay for, how to price it, and when developer adoption should trigger sales.
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Goal-Setting for AI Products: How I Plan, Prioritize, and Confidently Ship in a Nonlinear GenAI World
Planning AI roadmaps is fundamentally different from traditional software. I share how I set outcomes-first OKRs, balance research and product development, and scale safely without over-planning.…
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Engineering Leadership That Scales: Strategy, Velocity, and Org Design from Carta, Stripe, Uber, Calm
High-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…
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Inside Bard’s Playbook: How to Ship AI Fast, Build Ethically, and Outlearn Competitors
Building 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…
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Developer-First Growth: From Fast Activation to Revenue
A practical playbook for turning fast developer activation into team expansion, coherent packaging, and durable enterprise revenue.
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An Operating System for AI-Era Product and Engineering Leaders
A practical model for turning faster AI-assisted output into reliable customer outcomes through clear bets, evals, decision rights, and learning loops.
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Enterprise GTM: Build One System From Pipeline to Expansion
A practical operating model for connecting qualification, champions, pilots, onboarding, value realization, renewal, and enterprise expansion.
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From Product-Market Fit to Expansion: A Sequencing Model
A practical model for proving product-market fit, choosing the right expansion path, protecting the core, and scaling adjacencies with evidence.
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What Makes or Breaks Executive Hires: My Lessons on Fit, Red Flags, and Measuring Success
Executive 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…
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How to Create a B2B Category and Scale the GTM Motion
A practical operating model for choosing category creation, proving a practitioner wedge, designing monetization, and scaling from PLG to enterprise.
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Persuasive Leadership for Founders: My Take on Wes Kao’s Playbook to Influence and Win
Founders and product leaders don’t need more noise—they need persuasive clarity. In this first-person breakdown, I share how to align your message with your natural style,…
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When a Focused Product Wedge Is Ready to Become a Platform
A practical framework for deepening a winning wedge, extracting reusable platform primitives, and expanding without weakening product-market fit.
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Browse topics
- AI Strategy (317)
- Generative AI (106)
- IT Leadership (33)
- Leadership (76)
- Product Management (344)
- Product Management Leadership (308)
- Uncategorized (32)
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