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Spinning up an agent is like hiring a brilliant engineer on day one: capable of almost anything, completely in the dark about how your organization actually works. That gap is expensive, and most teams are only starting to feel it.
Dennis Pilarinos, founder and CEO of Unblocked, has been thinking about this problem longer than most. His argument is that the hardest part of software engineering was never writing code. It was always the context layered around it: the architectural call buried in a Slack thread, the incident postmortem that quietly changed a naming convention, the tribal knowledge that lived in someone's head until they left. AI made that problem viscerally visible. Agents burn tokens chasing answers that experienced engineers already carry.
Dennis and Rob dig into what it actually takes to compete on context beyond just indexing source code, why the pull request is quietly becoming the uber class of the modern SDLC, and why the tokenomics reckoning that's coming for engineering leaders might finally give us the through-line from AI spend to business outcomes that the industry has never had.
Dennis built developer tools across every major platform shift of the last 20 years, from the .NET framework at Microsoft to AWS, mobile CI at Buddybuild, and now agentic infrastructure at Unblocked.
- Why agents are "disgustingly inefficient" without organizational context
- The limits of source code alone, and what fills the gap
- How the pull request is changing form and function in an agentic world
- Context-powered code review and what it surfaces that standard tools miss
- Connecting AI spend to business outcomes: closer than ever, further than we think
- The 3-5% of engineers who are "AI-pilled" and what they've already figured out
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