Knowledge
The Catalog
A working library of skills, lessons, and artifacts from 12 years of shipping products.
Featured
Building an AI Knowledge Platform After 7 Years of Failure
Thirty systems, seven years of failure. I built an enterprise AI knowledge platform by starting where nobody else did — with the people.
Enterprise Data Strategy: 22 Datasets in 8 Weeks
A team spent three years landing one dataset. I changed the question — meet the data where it is, not where you wish it was.
From Zero Personalization to $300M in Monthly Volume
Seventy million users, every one treated the same. We didn't need a grand strategy — we needed a series of small, fast wins.
All Entries
Winning the Argument Is the Easy Part
I built the scoring model that chose our vendor. Leadership picked the one they knew. I pushed back and won. Then they watched me for months.
Building With AI: Why the System Matters More Than the Prompt
Most people write prompts. I build systems — 12 skills, 11 agents, 127+ automated lessons. The difference is product thinking, not engineering.
The First 30 Days Playbook: How I Diagnose Any Organization
Not 'listen and learn.' A diagnostic playbook for walking into any organization and building a product vision with a prototype in 30 days.
The Product Builder Era: Why PMs Must Ship to Survive
The PM role is splitting into builders who ship and coordinators who won't survive. After 12 years, I'm watching it happen.
AI-Assisted Development: A Practitioner's Honest Guide
I've used AI coding tools daily for over a year. Here's what actually works, what doesn't, and why 'vibe coding' is both real and misleading.
Being the Whole Product Function for a Small Team
When you're the only product person, you don't get to specialize. Here's what owning strategy through shipped product actually looks like.
Bridging Product and Engineering — The Translator's Playbook
You don't need to be the best engineer in the room. You need to understand enough to stop wasting their time.
The Build vs. Buy Decision Has Nothing to Do With Technology
I've evaluated a $500M data center investment and a free-tier hosting choice in the same career. The framework is the same. The stakes aren't.
What I've Learned Mentoring Hundreds of Product Managers
The most common mistake junior PMs make is trying to know it all. The fix is simpler and harder than they expect.
How to Run a Discovery Sprint That Actually Ships
Most discovery sprints produce insights. Mine produce working prototypes. Here's the difference.
When Leadership Wants the Wrong Thing
Your VP has a pet feature. Your data says it's wrong. Here's how I've navigated this without burning bridges — and the one time I almost did.
The Real Problem Is Never in the Brief
The brief describes the comfortable problem. The real one is political, structural, or both — and naming it means someone has to change.
The Tiger Team Playbook
Small team, clear mission, no interference. Here's how I've stood up tiger teams that ship in weeks what larger teams couldn't deliver in years.
Trust Is Built on Honesty, Not Polish
My peer review literally said 'Jon is sometimes too honest.' I took it as a compliment. Here's what I've learned about the trade-offs.
What I Learned From Getting a Product Estimate Wrong
I underestimated treating content as code. Estimates were wrong, scope was too big, and I had to make the hardest trade-off in product.
How LLMs Turned Customer Feedback Into Actionable Insights
63% negative response rate. 200-page reports nobody read. An LLM-powered pipeline cut NRR to 22% and surfaced $160M in savings.
The Prototype Always Wins the Argument
A COVID chatbot I built in days went to production. A data center ML model I championed saved $1.6M a year. In both cases, the prototype ended the debate.
Product Discovery: Why Listening First Is the Fastest Way to Ship
I asked questions for weeks that made people wonder if they'd hired the right person. Four promotions later, those questions were the reason.
How to Get a Zero-to-One Initiative Funded in a Large Org
My first proposal at a large org got stuck in review for months. I never made that mistake again. Here's what I do differently.