Why AI Coding Agents Keep Guessing | Context Gap & Code Intelligence with Dennis Pilarinos

Summary Dennis Pilarinos has spent nearly two decades building developer tools at Microsoft Azure, AWS, and Buddybuild (acquired by Apple). Now CEO of Unblocked, he's tackling the critical problem holding back agentic AI development: context intelligence. Why do AI coding agents keep guessing? Because they lack the organizational and business context behind the code. In this episode, the Overcommitted hosts dig into how developers and AI agents can truly understand the "why" behind codebases, not just the "what"—and why this matters for code quality, productivity, and shipping reliable tools. Links Dennis' email: dennis@getunblocked.com Unblocked: https://dub.sh/IeI82Vx Dennis on X: https://x.com/dennispilarinos Dennis on LinkedIn: https://www.linkedin.com/in/dennispi/ Hosts Overcommitted: https://overcommitted.dev Bethany Janos: https://github.com/bethanyj28 Brittany Ellich: https://brittanyellich.com Erika Eggemeyer: https://github.com/eggyhead