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CEO and Board Member of Stack Overflow, the world's most trusted…
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Prashanth Chandrasekar shared thisEnjoyed this SXSW Fast Company panel with Kc Ifeanyi, Sam Jordan and Peter Smart where I shared my perspective on how leaders can navigate the disruptive landscape of AI based on my own learnings of leading Stack Overflow during a very dynamic period --- and how Stack Overflow has pivoted to become the knowledge intelligence layer inside enterprises. Here are the top 5 takeaways: ⚡ Embrace a 'Refounding' Mentality: When a tectonic shift like AI occurs, don't just patch your existing business. You must be willing to revisit your mission and purpose—effectively "refounding" your company to remain relevant. ⚡ Carve Out Autonomous Teams: To successfully pivot, create an autonomous, purpose-built team that operates outside the pressures of the core business. This unit should have its own incentives, autonomy, and a clear timeline to experiment and disrupt from within. ⚡ Stay in the Trenches: For fundamental technological shifts, leadership cannot fully delegate. For a period of time, I personally led product initiatives during our transition to ensure the company moved with speed and focus. ⚡ Adopt a 'Fast, Focused, and Fearless' Mantra: Fast: Rapidly incorporate daily learnings into your strategy. Focused: Ensure you are solving real customer problems, not just using AI for the sake of it. Fearless: Be ready to change your entire business model if the data demands it. ⚡ Maintain a Growth Mindset: Leaders must be comfortable being wrong. Assumptions about AI capabilities will be proven untrue as technology evolves, so you must remain flexible, hold your points of view "loosely," and keep learning to remain resilient.Prashanth Chandrasekar shared thisDid Stack Overflow experience an identity crisis when ChatGPT reared its head? At the Fast Company Grill today, CEO Prashanth Chandrasekar discusses the challenges that the platform faced, and where it's headed next. #FCGrill #SXSW
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Prashanth Chandrasekar reposted thisPrashanth Chandrasekar reposted thisSaturday I got to sit down with Prashanth Chandrasekar (CEO of Stack Overflow), Peter Smart (CXO at Fantasy), and Kc Ifeanyi from Fast Company at the FC Grill during SXSW. Prashanth was really honest about what happened when ChatGPT showed up. Stack Overflow was the place every developer went for answers. Then overnight, anyone could get a code answer from a chatbot. Instead of trying to out-answer AI, they're pivoting toward becoming the verification layer. The place you go to know whether the answer is actually right. That's a completely different business than the one they were running two years ago. Peter made the case that companies need to start experimenting. Test things. Run hypotheses. Stop waiting for certainty. I agree with that in principle. But I pushed back a little because it's way easier to say than to do. Most leaders operate inside incentive structures that punish exactly that kind of behavior. You get measured quarterly. Your board wants metrics. The safest move is always the most visible, most incremental AI application, not the most transformative one. So when we tell leaders to "experiment more," we're asking them to be bold inside a system that rewards caution. If companies actually want experimentation and real hypothesis testing, they have to change the incentive structure first.
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Prashanth Chandrasekar shared thisEnjoyed my conversation with Cliff Saran of ComputerWeekly.com on Agentic AI workflows in software engineering and Stack Overflow's quickly evolving role via our enterprise product, Stack Internal. We dug into why the "Human-in-the-loop" is no longer optional—it’s the competitive advantage. We’ve entered the "Agentic Era." We’re moving past simple Copilots that suggest a line of code to autonomous Agents that can execute complex workflows. But there’s a catch: if that agent is grounded in stale, unverified data, it isn’t helping—it’s hallucinating. Here are the 5 shifts I’m watching closely as we work with enterprises to build the future of Stack Overflow with our Stack Internal product: ⚡ The Move to "Headless" Knowledge: Stack Overflow is no longer just a destination website. We are becoming the "Intelligence Layer" that cleans and verifies AI output directly inside your IDE and internal tools. ⚡Accepting "Inelegant" Code: AI-generated code is often "inelegant" by human standards, but in an era of pure velocity, "good enough" is becoming the new enterprise benchmark. Our job is to ensure it’s safe and functional. ⚡The "Star Trek" Future: I’ve always been a Trekkie. We are finally reaching the "Replicator" moment where the roles of Engineer, Product Manager, and Designer are merging. The new developer is a Captain orchestrating a fleet of agents. ⚡Solving "Documentation Rot": In the Agentic Era, static docs are a liability. We’re doubling down on "Living Knowledge" that stays in sync with your codebase in real-time. ⚡The Trust Anchor: AI can generate syntax, but humans provide context and trade-offs. That verified human DNA is the only thing that can close the Trust Gap. The goal isn't just to write code faster. It's to build better with the confidence that your AI actually knows what it’s talking about. Are you seeing a "Productivity Tax" in your org, or have you found the secret to AI trust? https://lnkd.in/g9N4fpDg #AI #GenerativeAI #StackOverflow #SoftwareEngineering #AgenticAI
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Prashanth Chandrasekar reposted thisPrashanth Chandrasekar reposted thisHappy SXSW week! Catch us in Austin this weekend at the 2026 Fast Company Grill. We will be welcoming the following leaders and innovators to the #FCGrill stage: Johannes Leonardo CEO Helen Andrews, Stack Overflow CEO Prashanth Chandrasekar, Ben & Jerry's co-founder Ben Cohen, Rare Beauty's Chief Impact Officer Elyse Cohen, Yahoo CEO Jim Lanzone, Away CEO Jessica Schinazi, Roku founder and CEO Anthony Wood, and Shit You Should Care About founder and CEO Lucy Blakiston. View our full list of speakers and four-day programming schedule here: https://bit.ly/4a8R3yN RSVP to reserve your spot: https://bit.ly/4rKD8Vv
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Prashanth Chandrasekar shared thisWe are noticing a clear shift on our public Stack Overflow site. As the world races to leverage the new abstraction layer of AI tools and AI agents for coding and other use cases, they encounter moments where they are stuck and need assistance from knowledgeable experts to progress forward. We are noticing a consistent and steady increase (month over month growth) in the following areas on our site: ⚡ Questions related to the new AI-driven software development workflow ⚡ Complex questions that have not been answered in the past ⚡ Our AI Assist agent which grounds our AI answers in our knowledge base ⚡ Opinion-based / subjective questions focused on advice, best practices, (vs. our traditional, strict Q&A) The need for trusted knowledge / context continues to increase significantly --- we see this in our enterprise business, where AI Agents are being built on top of our Stack Internal platform so that the AI agents are working off high quality, curated, validated, scored and trustworthy context inside the enterprise --- that sits on our platform via our knowledge ingestion and scoring layer, knowledge base, APIs and MCP server. Thanks to our amazing community and our Stackers for their continued contributions to Stack Overflow!
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Prashanth Chandrasekar shared thisOur new and modern experience of Stack Overflow is now available for all users in Beta! Several key updates: ⚡ Our AI Agent is central to the experience and is able to deliver trustworthy answers on any technology topic, rooted in our knowledge base ⚡ New subjective questions and answers (a frequently-requested feature from users) that are beyond our stricter canonical Q&A that delivers experience-based insights and peer recommendations ⚡ A central view of all sub-communities that the user is part of (users often forget we have 185 websites!) ⚡ Several usability improvements on layout, navigation Check it out and give us your feedback: https://lnkd.in/g3Hn-Rb3 Learn more about the changes: https://lnkd.in/gv5USHEq Thanks to our Stackers for working hard on this new design and philosophy for Stack!
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Prashanth Chandrasekar reposted thisPrashanth Chandrasekar reposted thisThere's a trust gap between developers and AI, and your team's knowledge is the only way to bridge it. Last week at #DeveloperWeek2026, our Chief Product and Technology Officer Jody Bailey took the stage for a keynote on the power of knowledge and context in AI software development strategies and how companies like Uber, Xerox, and HP are using Stack Internal, our knowledge ecosystem, to accelerate AI initiatives and supercharge their productivity. DeveloperWeek https://lnkd.in/eekZDYSe
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Prashanth Chandrasekar shared thisExcited about our momentum in Enterprise AI via Stack Internal. We are building with our enterprise customers to become the knowledge intelligence layer that captures critical, trustworthy context from humans and AI Agents inside the organization, so that it can be used for various Agentic AI use cases. In this 3rd mini video, our VP of Engineering, Peter O'Connor, describes Stack Overflow's bi-directional MCP server that allows technologists within companies to engage with and write automatically to Stack Internal from their AI coding assistant or wherever they spend time (e.g., Slack, MS Teams, IDE, etc.). Part 1: https://lnkd.in/gBSJESD9 Part 2: https://lnkd.in/g7QPaNGM Stack Internal: https://lnkd.in/e_5H7GPQ
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Prashanth Chandrasekar reposted thisPrashanth Chandrasekar reposted thisFor the last few years, fears of AI replacing human tech workers has colored much of the discourse around this new technology. But during his conversation with OpenAI's Romain Huet, our CEO Prashanth Chandrasekar shared one key truth about the AI tech revolution: AI—and the technologies around it—will create an infinite demand for human-generated code, creating more jobs for developers. Eira May take a closer look at how AI will drive new developer jobs, and what this work means for the developer community. https://lnkd.in/ezUMwPpt
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Prashanth Chandrasekar liked thisPrashanth Chandrasekar liked thisDid Stack Overflow experience an identity crisis when ChatGPT reared its head? At the Fast Company Grill today, CEO Prashanth Chandrasekar discusses the challenges that the platform faced, and where it's headed next. #FCGrill #SXSW
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Prashanth Chandrasekar liked thisPrashanth Chandrasekar liked thisAgility has become a survival skill for companies in the age of AI. During a Fast Company Grill panel at #SXSW this year, our CEO Prashanth Chandrasekar shared how enterprises can avoid the common missteps of the AI race and stay resilient during this once-in-a-generation technology shift. https://lnkd.in/egK3Ad7W
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Prashanth Chandrasekar liked thisPrashanth Chandrasekar liked thisPart of our team — Alex Semeniuk and Oleg Lysiak — spent a few days at SXSW, connecting with founders, builders, and product leaders from across the tech and AI ecosystem. The event was full of conversations, panels, and community events. We joined discussions with industry voices such as Prashanth Chandrasekar and Mati Staniszewski, who shared their perspectives on the future of software development and AI. SXSW week also brought together an incredible community across side events like Startup Mania, Capital Factory Backstage & Startup Crawl, Funded House®, Midwest House, and the European Founders x Funders Happy Hour. Great energy, great people, and many inspiring conversations. Thank you to everyone we had the chance to meet and talk with!
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Prashanth Chandrasekar liked thisPrashanth Chandrasekar liked thisWant to learn how Stack Overflow is evolving in the age of AI? Meet us April 6-9 at HumanX in San Francisco! 🤖 We'll be at Booth #705, where you can learn how Stack Internal is shaping the future of enterprise AI. Learn more about Stack Internal and set up a meeting with us at #HumanX2026: https://lnkd.in/e9VWUrx4
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Prashanth Chandrasekar liked thisPrashanth Chandrasekar liked thisDevelopers beware: while AI tools allow just about anyone to create working applications, they actually pose a growing risk for businesses. Our Senior Director of Engineering, 👨💻 Ben Matthews, writes for Digitalisation World about the dangers of bad AI generated code, from security risks to burnout and bottlenecks to longterm financial drain. https://lnkd.in/eK5JYRU4
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