tyler-gray:~$ whoami

Hey, I'm Tyler Gray.

Product strategy at Microsoft.

Pricing, packaging, and business models.

I shape what gets built.

Now I'm learning </> to build it myself.

// A working notebook. Product teardowns, pricing frames, and what I'm learning by experimenting with AI.

Projects

Side projects, teardowns, and experiments — a strategist exploring and learning about AI by getting hands-on.
2026 Coming soon
A

AI Monetization Decision Tree

AI Monetization Interactive

An interactive decision tree that walks you through AI monetization options — answer a few questions about your product and get to a recommended approach.

2026 Coming soon
F

Flight Turbulence Forecasting

Aviation Forecasting Monetization

Reverse-engineering how turbulence forecasts are generated, and exploring whether there's a product (and a business) hiding in better, more accessible predictions.

2026
A

Azure Case Study

Design UX Case Study

A deep dive into UX improvements and strategic opportunities for Azure's portal and compute offerings.

Writing

Notes on product strategy, personal stories, and what I'm learning from experimenting with AI.
On Overthinking A personal story about getting out of my own head
May 29, 2026
Personal
Coming soon
Tearing Down the GitHub AppMod Agent How it works, what's interesting, and what I'd take away from it
May 28, 2026
AI
Coming soon