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James Dillard
Product leader and operator with experience at Stripe and YouTube; recently spent three months embedded at Roo Code working on AI-native product and team practices.
Best podcasts with James Dillard
Ranked by the Snipd community
Oct 27, 2025
• 1h 3min
#81: I spent 3 months at an AI-native startup where every role ships code | James Dillard (Product Leader, ex-Stripe & YouTube)
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James Dillard, a product leader formerly with YouTube and Stripe, shares his insights from three months at Roo Code, an AI-native startup. He reveals how a 10-person team redefines coding norms, with every member contributing to the codebase regardless of role. Dillard discusses overcoming initial fears in coding, the evolution of pull request workflows with AI, and the integration of customer insights into rapid prototypes. He emphasizes the importance of training and experimentation for organizations looking to adopt an AI-native approach.
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