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

Ep 19: Community Is the New Moat: Stack Overflow’s Second Act with Prashanth Chandrasekar