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 Google

• What it takes to lead a “people transformation” during industry disruption

• The future of developer communities and the rise of agentic AI in the enterprise

• Why he believes community is more important than ever in the AI age

A must-listen for anyone building in AI, developer tools, or enterprise SaaS.

00:00 – Intro and Prashanth’s journey from Rackspace to Stack Overflow
05:30 – Rebuilding the team: leading a people and culture transformation
10:40 – How Stack Overflow built its enterprise SaaS motion
18:00 – The pivot from community and ads to enterprise and recurring revenue
27:00 – Lessons from leading through change: hiring slow, acting fast
27:30 – The OpenAI partnership and data licensing strategy
33:00 – Stack Overflow’s role in the AI tech stack
41:00 – How enterprises like Uber are building internal copilots using Stack Overflow data
45:00 – The economics of high-quality data and premium licensing
49:00 – The agentic AI opportunity in the enterprise
54:00 – How AI is changing software development and product velocity
1:00:00 – Why community will matter even more in the age of AI