AI agents have taken on a growing share of software development work, so much so that the hardest

problems are shifting away from code generation 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, agenic workflows. Dennis Pilarinos is the founder and CEO of Unblocked.

Previously, he helped build Azure at Microsoft, worked at AWS, and co-founded Buddy Build,

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 and 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 co-founded and served as CTO for two companies,

founded the San Diego JavaScript meetup, and organizes the AI inaction

discussion group through latent space.

Check out the show notes to follow KBall on Twitter or LinkedIn, or visit his website,

kball.l. LLC.

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