The End of Prompt Engineering with Dennis Pilarinos

from Founder Mode · host Kevin Henrikson and Jason Shafton

EPISODE 48Dennis 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 most when hiring in an AI-native era, and why the workflows teams rely on today, including pull requests, may look very different in the near future.CHAPTERS00:00 – Why AI coding tools fail without context04:03 – Building Unblocked to solve the missing layer in engineering12:11 – Where AI-generated code breaks in real production environments20:33 – Hiring for curiosity, ownership, and success in an AI-native world27:18 – Founder lessons from aviation, uncertainty, and staying groundedLINKSConnect with Dennis PilarinosUnblocked • LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

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This episode was published on March 19, 2026.

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