Organizational Context for AI Coding Agents with Dennis Pilarinos

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Mar 5, 2026

Dennis Pilarinos, Founder and CEO of Unblocked who built parts of Azure and co-founded BuddyBuild. He talks about context engineering for developers and AI agents. They cover where organizational context lives, reconciling conflicting sources of truth, permissions-aware runtime access, and how agent workflows change code review and developer roles.

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ADVICE

Make Context Permission Aware At Runtime

Enforce permissions at runtime so the context engine only uses data the requester can access.
Bind identities across GitHub, Slack, Notion to respect access rules during queries.

INSIGHT

Enrich Noisy Data With Derived Artifacts

Data enrichment is essential because teams rarely keep docs up to date.
Unblocked diffs every PR and embeds those changes to build a richer knowledge graph from existing artifacts.

ADVICE

Use Hybrid RAG With Agentic Tools

Combine lexical and semantic search in a hybrid RAG plus agentic approach to handle temporal and fuzzy queries.
Expose tools/APIs so orchestrators and agents can call the context engine programmatically.

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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 agentic workflows.

Dennis Pilarinos is the Founder and CEO of Unblocked. Previously, he helped build Azure at Microsoft, worked at AWS, and co-founded BuddyBuild, which is a mobile CI platform acquired by Apple. Dennis joins Kevin Ball to discuss context engineering, reconciling conflicting sources nof truth, permission to wear AI systems, the shifting bottlenecks in the software development lifecycle, and what it means to be a software engineer in an increasingly agentic world.

Full Disclosure: This episode is sponsored by Unblocked.

Kevin Ball or KBall, 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.

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