Stack Overflow CEO Prashanth Chandrasekar on embracing AI

Since it was founded in 2008, Stack Overflow has become the go-to source for IT developers looking to share their knowledge and solve coding problems. In 2015 it secured $40 million in Series D funding, which helped push it into the top 50 sites on the web.

At the peak of its popularity, the company was attracting around 50 million monthly active users, with around 150,000 questions being posted to the site every month.

However, since 2019 – other than a slight spike during the pandemic, where isolated developers looked to the site for support – there’s been a steady decline in the number of questions being posted. At the end of 2022 this was hastened by the launch of ChatGPT.

In this Q&A, ITPro speaks to Stack Overflow CEO Prashanth Chandrasekar about the challenges Stack Overflow currently faces and how the company is navigating the huge disruption caused by generative AI tools.

There’s been a big focus on developing enterprise partnerships within Stack Overflow, especially with AI companies. How did that come about?

On the enterprise side, we have noticed a tremendous amount of interest in our data, which has been proven to be very useful because most of the big AI companies have leveraged it to get their products out. Early on, when we put up anti-scrapers and really said look, you've got to work with us more officially, most of them came back and said they'd love to work with us. And so that's what we've done.

How are you adjusting to generative AI at Stack Overflow?

The statement we use inside the company is “Go to wherever the users are”. So the idea is that we integrate into all these different places. With a lot of these partnerships that we have with Google, OpenAI, Microsoft,GitHub – all these folks – we're integrating into their tools. Then if the [generative AI] tool is unable to give you the answer that you need, you're bringing people back to the site, so the community can answer those questions.

Has your focus on enterprise created tension within the broader Stack Overflow community?

I don't think there's a real tension between the two. That's just how our business model is set up. But they're not in opposition to each other. The number of questions that we started seeing on the site definitely went down. They went down because the simple questions that were being asked previously on the site, which were always getting closed out or tagged as duplicates, no longer get asked. People tend to use some other AI tool to do that. And that's actually not a bad thing.

Over the years Stack Overflow has gained a reputation amongst developers for its over-zealous moderation and its often-chilly reception to new users. Is this being addressed?

We have now changed that and we want to serve developers of all kinds. We're not some sort of elitist place, where it's supposed to just be the best programmers in the world. That doesn't make a lot of sense. It's all about how we embrace the new folks who are interested in this space, open it up so that they are all learning from each other.

Can you tell us how the last couple of years have been for Stack Overflow?

I would say we've been on a definite journey, taking what was a very stark event in November of 2022 [the launch of ChatGPT], which could have been a very big headwind for the company, and turning it into a tailwind. We’ve expanded the scope of our community, which was previously just a knowledge base of about 60 million questions and answers, formed for the past 16 years. And we have been actively expanding the scope, going from a knowledge base to a community for technology enthusiasts.

How have you made Stack Overflow more welcoming?

We have now opened up multiple ways in which beginners can actually use the site and get a friendlier experience. So, for example, the question asking experience now involves AI, with every question being run through an AI assistant, which is powered by Google Gemini. If a question is a duplicate you're going to get a friendly response from the AI assistant. You're not going to get humiliated in front of the world.

So this is a major shift for Stack Overflow, which has traditionally been geared towards professional developers?

Previously our focus and core audience was developers. And that developer was probably more experienced, especially on the contributor side, because the standards were very high. Now the explicit role for us is that we want to serve the technology enthusiast. So that's very different, but we believe there's going to be a lot more technology enthusiasts in the future. And the barrier to entry when writing code keeps dropping, because everybody can now vibe code using AI tools.

We are expanding into more community features. Looking at questions like how you get humans to connect on the site. And how do you make sure that we are helping them with their learning and with their careers. Because there’s going to be disruption to technology jobs as a result of AI, so we need to consider how we can help them with things like reskilling and embracing AI tools as they move forward. And, in a world of AI slop, we need to remain the most accurate and trustworthy knowledge base.

One of the major issues surrounding AI tools being trained on Stack Overflow expertise is the matter of contribution. Is this something you’re looking at?

There's quite a bit of discussion about contribution at the moment, which is how do we make sure we recognize folks appropriately when their content is used in any of these AI tools? When people came to an answer via Google, the view count of that answer would keep going up. So we would often say, for example, “Hey Dan, your answer from six years ago has been viewed a billion times. Congratulations!” There should be something similar for AI tools.

How are you approaching the task of communicating such a major shift?

We are actively thinking about our brand, to reflect what I just described, which is to move from a knowledge base to a community. The question is, is there value in being part of a tech enthusiast community, where you share with each other, learn with each other, and grow your careers together? This community will see a huge expansion in this next generation. And so, for us, it's about making sure that we respect the views of our original users, but also lean into the future, because that's where the world's headed.