ThinkingApril 4, 2026

The 5-Company View: Patterns I See as a CAIO

This essay is in progress. Check back soon.

When you're the CAIO for five companies at once, you see the same conversations play out in different industries with the same outcomes. Here's what I see.

The Same Five Conversations

Where AI Actually Lands

The CAIO Superpower

What This Means for Founders