Organizational Context for AI Coding Agents with Dennis Pilarinos

AI agents have taken on a growing share of software development work, so much so that the hardest problems are shifting away from cogeneration towards something new. Context. The challenge is now contextualizing why systems work the way they do, how architectural decisions were made, and the sources of truth that exist outside of the code base. As teams adopt agentic tools, gaps or inconsistencies in context have emerged as a primary reason why software fails to meet production standards. Unblocked is a startup focused on solving this context gap. Their context engine aggregates and reasons over organizational knowledge spread across source code, pull requests, documentation, chat systems, and production telemetry. By acting as a context engine for both developers and AI agents, Unblocked aims to improve AI code quality and review, reduce interruptions, accelerate onboarding, and enable safer, more effective agentic workflows. Dennis Pilorinos is the founder and CEO of Unblocked. Previously, he helped build Azure at Microsoft, worked at AWS, and cofounded BuddyBuild, which is a mobile CI platform acquired by Apple. Dennis joins Kevin Ball to discuss context engineering, reconciling conflicting sources of truth, permission aware AI systems, the shifting bottlenecks in the software development life cycle, and what it means to be a software engineer in an increasingly agentic world. Kevin Ball or k Ball is the vice president of engineering at Mento and an independent coach for engineers and engineering leaders. He cofounded and served as CTO for two companies, founded the San Diego JavaScript Meetup, and organizes the AI in action discussion group through Latent Space. Check out the show notes to follow Keball on Twitter or LinkedIn, or visit his website, keball.llc. Dennis, welcome to the show. Thanks very much. Thanks for having me. Yeah. I'm really excited to learn about what you're up to. But let's start a little bit with you. So can you give our listeners a little bit of your background and what led to Unblocked? Sure. I'm Dennis Pilrinos. I'm the founder and CEO of Unblocked. I've been building developer tools for the better part of twenty years. My career started in earnest at Microsoft, where I was one of the earliest people to think about shifting on premise computing APIs to cloud hosted APIs. So it was part of the team that built a lot of the Azure platform. I worked in AWS. I started a company called BuddyBuild, which is a CI platform for mobile app developers, which is acquired by Apple. So about three years after we started it, I've worked at Apple for about a year and a half. And basically through that series of, like, lived experiences and life experience, we took a lot of that to go and build Unblocked. And so Unblocked helps engineers get the context that they need to get their jobs done. So that's really kind of my background and a little bit about what we're trying to do at Unblocked. Yeah. So let's talk about that word …