// Podcast

Context Window

AI, Insurance & The Humans Behind It

// What to expect

Context Window is Dearborn Labs' podcast for the leaders, operators, and founders working at the intersection of AI and enterprise operations. Each episode is a candid conversation with the people actually putting AI into production inside legacy industries like insurance — what's working, what isn't, and what it really takes to move from pilot to production.

// Latest Episode

Episode 10: Why the Biggest AI Winners Won't Be the Ones We Expect
NOVEMBER 12, 2026•DURATION: 64 MIN•EPISODE 10

Why the Biggest AI Winners Won't Be the Ones We Expect

Patrick Charles, Global Head of P&C Programs at SiriusPoint, on why there's no doubt we're in an AI bubble, why he still believes AI will change insurance the way the internet did, and why his team says no to most of the MGAs that come knocking.

// Weekly Despatch

New episodes drop regularly. Follow us.

Bring us the workflow you’ve already tried to fix.

A decade of running an AI-native carrier, pointed at one of your workflows for four weeks.