About
I've spent 25+ years in the middle of major technology shifts. Not the slide deck version — the part where you actually have to make it work.
Across roles at Microsoft and Stripe, I built platforms that are still running: Microsoft Learn, Microsoft Docs, Stripe Docs. Developer experience, documentation, operating models — the kind that keep working after the team that built them has moved on. The pattern is always the same: big strategy meets messy reality, and someone has to close the gap. That's always been the work.
Right now, that gap is AI.
Most enterprises I talk to aren't short on interest. They've seen the demos. They've run the pilots. What they're missing is the bridge between "AI is clearly useful" and "AI is actually integrated into how we make decisions and ship work." That's where I live.
So I built Obaron — an AI Readiness auditor for developer docs. Free Lightning Scan: put in your domain, get a score in 60 seconds. $49 Docs Readiness Audit: 30 pages deep, category breakdowns, a prioritized fix list. AI Readiness, in the narrow sense: how well AI systems can understand, retrieve, cite, and act on your content.
I shipped it in four days. That number is real, and it has context: a working prototype from a year of building while figuring out what AEO even meant, a fluency with AI-native workflows I've been developing since before that, and 25 years of knowing what a shippable thing looks like. The AI made it fast. The experience made it real.
Greatest Hits
- Obaron — AI Readiness auditor for developer docs. You put in your domain, get your AI Readiness Score and a report of exactly what's blocking AI agents from finding your content. Shipped in four days.
- AI All The Things — 45 fix-logs from real agent builds. Not tutorials: the actual error, the wrong fix, and what worked.
- Stripe Docs — helped upgrade the documentation platform for one of the most developer-loved APIs on the planet
- Microsoft Learn — scaled Microsoft's developer learning platform to millions of monthly users
- Microsoft Docs — helped move all of Microsoft's technical documentation from MSDN to the open web
- Xbox Apps — shipped apps on the console people actually played games on
- Windows Phone Apps — shipped apps on the console people... didn't
- Silverlight — the browser plugin era, in all its glory
- MIX Conference — Microsoft's web and design conference which was too cool to continue
- Channel 9 — developer video community before YouTube ate everything
- Unreal Tournament — yes, that one. Made maps. Fragged people. No regrets. Bombing Run!
- Formula Boats — built the website for a company that built actual boats. With fiberglass. The original "shipping"
- US Army — where I learned that systems thinking isn't optional
The pattern: platform work. Not features — the layer that features run on.
Let's Talk
If you're the one who has to make the AI strategy actually work — in the product, in the code, in the room where it has to run — reach out. I want to hear about your specific gap.