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Your AI looks 80% done. In reality, it's 20% done, and the last mile is a cliff. Greg Whalen, CTO of Prove AI, breaks down why CTOs are getting blindsided by AI, why vibe coding creates a false sense of progress, and what most teams are missing when it comes to AI telemetry and observability.

Greg has led engineering at global scale as CTO of ZendIt, GM for Amazon WorkMail at AWS, and was an AI researcher at Columbia's NLP group. Now he's building Prove AI to help enterprises move from "mostly working" to production-grade AI systems.

We dig into: why AI isn't just another tool in the toolbox, the morning coffee debugging nightmare, how agents exploit other agents for restricted data, why thumbs up/down tells you nothing about outcomes, the vibe coder vs. super principal divide, why CTOs need to "get back in the ring," and why being a first mover beats waiting for convergence that isn't coming.

Prove AI → https://proveai.com

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