Jeff Winter 6/26/26 Jeff Winter 6/26/26

What Matters Most When Scaling AI in 2026

The hardest part of scaling AI is not deciding what matters, it is diagnosing what matters most right now.

Jeff Winter 6/25/26 Jeff Winter 6/25/26

Why AI Strategy Feels Like the World’s Hardest Escape Room

AI strategy feels a lot like an escape room: everyone walks in confident, the clues are scattered across departments, the clock is ticking, and suddenly the hardest part is not the technology but figuring out how the business actually gets out.

Jeff Winter 4/10/26 Jeff Winter 4/10/26

Automation Vs. Agency Vs Autonomy

There is a massive structural difference between a system that executes a rule and one that chooses a path, and mixing them up is an expensive mistake.

Jeff Winter 11/20/23 Jeff Winter 11/20/23

Pilot Purgatory

Uh oh, the 'Pilot Purgatory' card has been played at your company. What is your next move?