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The End of Prompt Engineering with Dennis Pilarinos

EPISODE 48

Dennis Pilarinos joins Kevin Henrikson and Jason Shafton to unpack what AI in software development actually looks like beyond the demos, arguing that the real bottleneck is not code generation but context. Drawing on his experience building Buddybuild, working inside Apple, Amazon, and Microsoft, and now leading Unblocked, Dennis explains why source code alone is not enough for either engineers or AI agents to succeed, how historical decisions buried in Slack, Jira, and docs shape production-safe software, where AI-generated code breaks down in legacy systems, what traits matter…

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