Live from re:Invent…it’s Stack Overflow!
Ryan is joined by Stack Overflow’s CEO Prashanth Chandrasekar and Director of Data Science Michael Foree on the floor at re:Invent to discuss all they’ve seen and heard at the event, from the future of AI agents to the trust issues the enterprise has around AI and the impact of AI and robotics on the job market.
Episode Notes:
This episode was recorded at AWS re:Invent 2025! Check out Ryan’s recap of events from the floor on our blog.
Connect with Prashanth on LinkedIn.
Connect with Michael on LinkedIn.
TRANSCRIPT
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Stack Overflow users don't trust AI. They're using it anyway
Stack Overflow CEO Prashanth Chandrasekar was last on the show in 2022 — just one month before ChatGPT launched and upended literally everything for Stack Overflow in a deeply existential way.
He called a company emergency, reallocated about 10 percent of the staff to figure out solutions to the ChatGPT problem, and made some pretty huge decisions about structure and organization to navigate that change — all of it pure Decoder bait.
Links:
2025 Developer Survey | Stack Overflow
The people who make your apps go to Stack Overflow for answers | Decoder
OpenAI, Stack Overflow partner to bring technical knowledge to ChatGPT | The Verge
Stack Overflow feeds programmers’ answers to AI whether they like it or not | The Verge
Stack Overflow cuts 28 percent of its staff | TechCrunch
AI-generated answers temporarily banned on Stack Overflow | The Verge
Stack Overflow’s strike is over, but problems persist | Jon Ericson
A new era of Stack Overflow | Stack Overflow
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Credits:
Decoder is a production of The Verge and part of the Vox Media Podcast Network.
Decoder is produced by Kate Cox and Nick Statt and edited by Ursa Wright. Our editorial director is Kevin McShane.
The Decoder music is by Breakmaster Cylinder.
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#254 Prashanth: Why Developers Still Trust Stack Overflow in the Age of AI
This episode is sponsored by Oracle. OCI is the next-generation cloud designed for every workload – where you can run any application, including any AI projects, faster and more securely for less. On average, OCI costs 50% less for compute, 70% less for storage, and 80% less for networking. Join Modal, Skydance Animation, and today's innovative AI tech companies who upgraded to OCI…and saved.
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In this episode of Eye on AI, host Craig Smith speaks with Prashanth Chandrasekar, CEO of Stack Overflow, about how one of the internet's most trusted platforms for developers is adapting to the era of generative AI. With over 60 million human-curated Q&A pairs, Stack Overflow is now at the center of AI development — not as a competitor to large language models like ChatGPT, but as a foundational knowledge base that powers them.
Prashanth breaks down how Stack Overflow is partnering with OpenAI, Google, and other LLM providers to license its data and improve AI accuracy, while also protecting the integrity of its community. He explains the rise of OverflowAI, how Stack Overflow for Teams is fueling enterprise-grade co-pilots, and why developers still rely on expert human input when AI hits its "complexity cliff." The conversation covers everything from hallucination problems and trust issues in AI-generated code to the monetization of developer data and the evolving interface of the web.
If you want to understand the future of developer tools, AI coding assistants, and how human knowledge will coexist with autonomous agents, this episode is a must-listen.
Subscribe for more deep dives into how AI is reshaping the world of software, enterprise, and innovation.
Stay Updated:
Craig Smith on X:https://x.com/craigss
Eye on A.I. on X: https://x.com/EyeOn_AI
(00:00) Intro
(02:31) Prashanth's Journey from Developer to CEO
(05:18) Why Stack Overflow is Different from GitHub
(08:51) The Power of Community and Human-Curated Knowledge
(12:53) Stack Overflow's Data Strategy for AI Training
(17:26) Why Stack Overflow Isn't Competing with OpenAI
(20:36) How Stack Overflow Powers Enterprise AI Agents
(26:13) OverflowAI, Gemini, and the Future of Dev Workflows
(30:09) Inside Stack Overflow for Teams
(33:29) Safeguarding Quality: The Fight Against AI Slop
(38:32) Licensing, Attribution, and Protecting the Knowledge Base
(43:19) Business Strategy in the Age of Generative AI
An AI future free of slop
Read more about Stack Overflow’s future here.
Learn more about HumanX here. Missed it this year? The event takes place again on April 7-9, 2026 in San Francisco. Early birds can register here.
Follow Prashanth on LinkedIn or explore his posts on our blog.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The people who make your apps go to Stack Overflow for answers – here's how it works
Today I'm talking to Prashanth Chandrasekar the CEO of Stack Overflow – a highly specialized kind of social network, with a really unique business model. If you don't know Stack Overflow is a major part of the modern software development landscape: it’s where developers come together, ask questions, and get answers about how to build software, including actual code they can use in their own projects. It’s basically a huge question and answer forum. More than 100 million people visit Stack Overflow every single month. The company also sells Stack Overflow as an internal forum tool that big companies can use for their own teams: Microsoft, Google, Logitech—you name it, they’re using Stack Overflow to coordinate conversations between their engineers.
The platform has a long reputation of elitism; Prashanth himself is a developer and he told me his own first experience on Stack Overflow was a negative one. In fact, he took over as CEO about three years ago, after a pretty serious moderation controversy that saw several longtime Stack Overflow moderators quit. I wanted to talk to Prashanth about how it works, how the company makes money, and how to grow such a specialized user base while still being welcoming to new people.
Links:
Software-as-a-Service (SaaS)
Stack Overflow Sold to Tech Giant Prosus for $1.8 Billion
Stack Overflow helps millions of developers do their jobs every single day. Its new CEO says the next stage of its growth is selling to businesses.
Big Tech's hiring freeze unlocks rich talent pool for U.S. startups
Stack Overflow raises $85M in Series E funding to further accelerate SaaS business
Chris Dixon thinks web3 is the future of the internet — is it?
Stack Overflow Has a New Code of Conduct: You Must 'Be Nice'
Code of Conduct - Stack Overflow
Eight great sites that offer online classes
The other side of Stack Overflow content moderation
Everything you need to know about Section 230
Transcript:
https://www.theverge.com/e/23185361
Credits:
Decoder is a production of The Verge, and part of the Vox Media Podcast Network.
Today’s episode was produced by Creighton DeSimone and Jackie McDermott and it was edited by Callie Wright.
The Decoder music is by Breakmaster Cylinder. Our Sr Audio Director is Andrew Marino and our Executive Producer is Eleanor Donovan.
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Building Technical Communities at Stack Overflow with Prashanth Chandrasekar - #526
In this special episode of the show, we’re excited to bring you our conversation with Prashanth Chandrasekar, CEO of Stack Overflow. This interview was recorded as a part of the annual Prosus AI Marketplace event.
In our discussion with Prashanth, we explore the impact the pandemic has had on Stack Overflow, how they think about community and enable collaboration in over 100 million monthly users from around the world, and some of the challenges they’ve dealt with when managing a community of this scale. We also examine where Stack Overflow is in their AI journey, use cases illustrating how they’re currently utilizing ML, what their role is in the future of AI-based code generation, what other trends they’ve picked up on over the last few years, and how they’re using those insights to forge the path forward.
The complete show notes for this episode can be found at twimlai.com/go/526.
SaaStr 399: Four Steps to Scaling to $250M, While Keeping Community at Your Center with Prashanth Chandrasekar, CEO @ Stack Overflow
Building the world's largest and most trusted software developer and technologist community and going from 0 to 120 million users happened rapidly for Stack Overflow. Hear four steps from its CEO, Prashanth Chandrasekar, on how your product-led startup can grow its community and its revenue.
Video and blog post: https://www.saastr.com/four-steps-to-scaling-to-250m-from-stack-overflow/
Stack Overflow's CEO reflects on his first year
You can find a more in depth discussion of these topics on our blog. Prashanth shares his ideas about the importance of community and what it means to be a product led company.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Democratizing Software Development on Stack Overflow with Prashanth Chandrasekar
About Prashanth Chandrasekar
Prashanth Chandrasekar is Chief Executive Officer of Stack Overflow and is responsible for driving Stack Overflow’s overall strategic direction and results. Prashanth is a proven technology executive with extensive experience leading and scaling high growth global organizations. Previously, he served as Senior Vice President & General Manager of Rackspace’s Cloud & Infrastructure Services portfolio of businesses, including the Managed Public Clouds, Private Clouds, Colocation and Managed Security businesses. Before that, Prashanth held a range of senior leadership roles at Rackspace including Senior Vice President & General Manager of Rackspace’s high growth, global business focused on the world's leading Public Clouds including Amazon Web Services (AWS), Microsoft Azure, Google Cloud Platform (GCP) and Alibaba Cloud, which became the fastest growing business in Rackspace’s history. Prior to joining Rackspace, Prashanth was a Vice President at Barclays Investment Bank, focused on providing Strategic and Mergers & Acquisitions (M&A) advice for clients in the Technology, Media and Telecom (TMT) industries. Prashanth was also a Manager at Capgemini Consulting where he managed Operations transformation engagements and consulting teams across the US. He holds an MBA from Harvard Business School, an M.Eng in Engineering Management from Cornell University and a B.S. in Computer Engineering (summa cum laude) from the University of Maine. Prashanth is married and has two children.
Links Referenced
Twitter
Rackspace
Stack Overflow
Stack Exchange
Scripting the next era of Stack Overflow
Three months ago, we interviewed Prashanth during his first week on the job. Now, with a full quarter of work under his belt, our new CEO reflects on what we accomplished over the last decade and lays out his vision for where Stack Overflow, as a company and community, will be heading over the next year and beyond.
Paul explains why engineers prefer to give blunt feedback, even in a public setting.
Sara drops some hints about our plans for the future of the Stack Exchange network. One of these big goals is to better integrate knowledge from these with the activity that happens on Stack Overflow, so that the knowledge being shared on Server Fault or Super User can easily be found by users on Stack Overflow, and vice versa. Stay tuned for more details and feel free to share your thoughts for what would work to improve the user experience.
Prashanth talks about the forces reshaping the developer landscape: cloud services, machine learning, container orchestration, and more. How can we help new developers, both hobbyists and professionals, find what they need on our sites, and empower them so they feel comfortable asking questions and providing answers.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.