How Stack Overflow is competing with AI - Jody Bailey (CPTO, Stack Overflow)

AI has changed the way developers work—and Stack Overflow is right at the centre of that shift. In this episode, Jody Bailey, CPTO at Stack Overflow, shares how the platform is adapting to AI, protecting its community, and embracing new revenue streams. We explore how LLMs are reshaping developer behaviour, why canonical answers still matter, and what it takes to keep trust, quality and community alive in the age of instant AI-generated code. If you’re working on dev tools, building with AI, or just wondering how to keep your product relevant through disruption, this one’s for you.

Key takeaways

• AI is both a disruptor and an enabler
• Engagement is shifting, not disappearing
• Community remains the core asset
• AI doesn't kill quality—it challenges it
• Prompt engineering is the new entry-level skill
• Innovation is iterative—even with AI
• Stack is designing for tomorrow’s engineers
• Jody’s vision is long term

Chapters
00:00 – intro to Jody Bailey and his role at Stack Overflow
03:30 – impact of AI and shift in how developers search for answers
07:45 – Stack’s new business model: licensing data to LLMs
10:15 – protecting community-contributed data and enforcing attribution
13:20 – changing nature of search and the role of AI
17:00 – trust, verification, and the evolving user experience
21:10 – internal AI experiments and lessons learned
25:00 – balancing community, learning, and AI-powered answers
28:20 – new skills required for developers in an AI world
31:40 – evolving engineering roles and the future of team structures
36:10 – making Stack Overflow accessible for the next generation
39:50 – what Jody’s most excited about for the future

Featured Links: Follow Jody on LinkedIn | Stack Overflow | ‘Yes, Artificial Intelligence Has A Creative Side, Sort Of’ feature at Forbes

Our Hosts
Lily Smith enjoys working as a consultant product manager with early-stage and growing startups and as a mentor to other product managers. She’s currently Chief Product Officer at BBC Maestro, and has spent 13 years in the tech industry working with startups in the SaaS and mobile space. She’s worked on a diverse range of products – leading the product teams through discovery, prototyping, testing and delivery. Lily also founded ProductTank Bristol and runs ProductCamp in Bristol and Bath.

Randy Silver is a Leadership & Product Coach and Consultant. He gets teams unstuck, helping you to supercharge your results. Randy's held interim CPO and Leadership roles at scale-ups and SMEs, advised start-ups, and been Head of Product at HSBC and Sainsbury’s. He participated in Silicon Valley Product Group’s Coaching the Coaches forum, and speaks frequently at conferences and events. You can join one of communities he runs for CPOs (CPO Circles), Product Managers (Product In the {A}ether) and Product Coaches. He’s the author of What Do We Do Now? A Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.