Stack Overflow has been the home for developers for over a decade — but the rise of AI is changing everything. In this episode, we talk to Prashanth Chandrasekhar, CEO of Stack Overflow, about how he’s reinventing the company from an ad-based community platform to an enterprise SaaS and data licensing business at the center of the AI ecosystem.We discuss:How Stack Overflow’s data powers models from OpenAI and GoogleWhat it takes to lead a “people transformation” during industry disruptionThe future of developer communities and the rise of agentic AI in the enterpriseWhy he believes community is more important than ever in the AI ageA must-listen for anyone building in AI, developer tools, or enterprise SaaS.00:00 – Intro and Prashanth’s journey from Rackspace to Stack Overflow05:30 – Rebuilding the team: leading a people and culture transformation10:40 – How Stack Overflow built its enterprise SaaS motion18:00 – The pivot from community and ads to enterprise and recurring revenue27:00 – Lessons from leading through change: hiring slow, acting fast27:30 – The OpenAI partnership and data licensing strategy33:00 – Stack Overflow’s role in the AI tech stack41:00 – How enterprises like Uber are building internal copilots using Stack Overflow data45:00 – The economics of high-quality data and premium licensing49:00 – The agentic AI opportunity in the enterprise54:00 – How AI is changing software development and product velocity1:00:00 – Why community will matter even more in the age of AI

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