Episode 239: Navigating the AI Shift at Stack Overflow with Jody Bailey

27 Aug 2025 • 38 min • EN
38 min
00:00
38:10
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Jody Bailey, the Chief Product and Technology Officer at Stack Overflow, joins Melissa Perri to discuss the integration of AI and product strategy in one of the world’s largest online communities for technologists. Jody shares insights on how Stack Overflow is navigating the rapid technological advancements and adapting to maintain long-term trust within its community. They delve into the challenges and opportunities AI presents and how it influences product management at Stack Overflow. Curious about how AI is reshaping the product landscape and how Stack Overflow is positioning itself in this new era? Tune in to discover how Jody Bailey is leading the charge at the intersection of technology and community. You'll hear us talk about:06:52 - Building Trusted AI Knowledge for Enterprises Jody Bailey describes Stack Overflow's enterprise solution that maintains a positive feedback environment and identifies subject matter experts. He emphasizes the need for a trusted knowledge layer to manage and distribute proprietary information within organizations.13:43 - Leveraging Core Strengths in the AI Era Jody discusses how Stack Overflow is focusing on its core strengths, such as human connection and technical information, to position itself as a vital source for technologists in a world increasingly turning to AI tools for quick answers.19:52 - Trust, Adoption, and the Limits of AI in Development Work The conversation covers the importance of trust in Stack Overflow's community and how the platform ensures transparency and reliability, especially when integrating AI into its offerings. Jody highlights the need for a balanced approach to using AI without compromising on human interaction and knowledge. Episode resources: Jody on LinkedIn: https://www.linkedin.com/in/jodybailey/ Stack Overflow: https://stackoverflow.com/ Check out Monday dev: http://monday.com/dev Check our courses: https://productinstitute.com/ Timestamps: 00:00 Coming Up 02:18 From retirement to Stack Overflow 06:52 Building trusted AI knowledge for enterprise 12:19 Redefining Stack Overflow’s strategy for the AI era 19:52 Trust, adoption, and the limits of AI in dev work 26:08 Keeping junior roles relevant in an AI future 32:22 Internal transparency and advice for ambitious leaders

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