How Stack Overflow’s new CEO plans to kickstart enterprise growth

Stack Overflow has long been the Q&A site of choice for developers. But while that’s what most people know the company for, it has also built out a jobs site and Teams, its private Q&A service for enterprise clients, over the years. Now, it’s looking to capitalize on that and kickstart growth of Teams, especially, under its new CEO, Prashanth Chandrasekar.

Chandrasekar, a former investment banker and Rackspace exec, took over as Stack Overflow’s CEO. Teresa Dietrich, who was previously at McKinsey New Ventures, joined him at the beginning of the year as the company’s chief product officer. Ahead of today’s Teams product update, which mostly includes a number of new integrations, I sat down with Chandrasekar and Dietrich to talk about the company’s plans for the future and the role Teams will play in that.

Chandrasekar tells me that Stack Overflow itself, even after 12 years, has about 50 million monthly users. In addition, another 70 million each month visit the rest of the Stack Exchange sites around culture, science and other topics.

The Stack Overflow jobs product accounts for about half of the company’s revenue, he also noted. “That’s the very steady business that has existed for all of the entire duration of the company’s life,” he said. Ads and the Teams product split the remaining 50%, but it’s the two-and-a-half-year-old Teams service that is seeing the strongest growth now, with revenue nearly doubling year-over-year. “Our expectation is that in the next couple of years, it’ll become the primary business for us,” he said, adding that this is also why he took this job.

“The company has always done a great job creating these products and the community continues to thrive,” Chandrasekar said. “But at the same time, there was a recognition that for us to really scale this in the context of a true SaaS company, you need several fundamental components we had to put in place.”

The first task was to bring in someone who had experience scaling organizations, which is why Chandrasekar was hired. He also brought on Dietrich as CPO, as well as new VP of Customer Success Jeff Justice (formerly with Dropbox), and will soon announce a new chief revenue officer. “All these components we’ve put in place so that we can actually be a high-scale SaaS company,” said Chandrasekar. “That’s really where we’re headed.”

“I like solving complex problems and I think this sort of product ecosystem is a nice complex problem to solve in that we have B2C with our public platform and advertising, B2B2C with talent and then B2B with Teams,” Dietrich said when I asked what attracted her to Stack Overflow.

“I joined because I thought the challenge of building technology products with technologists, for the biggest technology community in the world to be sold to technology companies or technology employers, was like the pinnacle of all my background and my experience — and the scale and the scope with which Stack Overflow was already doing it — plus the opportunity down the line — was really compelling and it felt like that was at the right level of complexity and the real sort of ambitious opportunity for us down the road from here.”

As the company looks to ignite this kind of SaaS growth, it has to keep its existing community happy, something Dietrich is keenly aware of. She said the goal is to ensure that there is a virtuous cycle between the different lines of business, the public platform and, by extension, the community. But she also wants to bring more diversity into the community, which is currently 90% male, for example.

“When I think about inclusion within Stack Overflow, I think about a couple of things,” she said. “We have one paradigm which is QA. How could we have other paradigms that are still tight but actually are different ways for people to provide their expertise and increase their reputation? How do we not only reward the behavior of just having expertise but how [do we] reward behavior that is about collaboration and bringing other people along in apprenticeship of other people in this community.”

From a business perspective, though, the company’s focus is clearly on Teams. Chandrasekar said the playbook for successful SaaS companies has been around for years now, and he plans to draw from that and his experience at Rackspace.

Just like a younger startup, Stack Overflow “definitely” seeks to raise new funding to fuel its growth, said Chandrasekar. “Luckily, through just the tremendous hard work of the team, we did not have to raise a tremendous amount of capital in the last few years. The last round was in 2015, our Series B round, and we have obviously top VCs on our board, but the goal is to raise our next round before the end of the year.” He said the objective is to accelerate the company’s enterprise traction now that it sees positive signs around these products.

That process, he said, will also include a more aggressive international expansion for those products. There, too, the talent product is doing quite well. Looking ahead, Chandrasekar said he’s thinking about how Stack Overflow for Teams can reach non-technical teams.

“We’re beginning to see an expansion of the use cases beyond technical teams, much like that perhaps Slack had during their early days. This capability of just being on the same page with evergreen content that doesn’t have to be answered again and again, is very relevant for organizations beyond the core development organization,” he noted, and Dietrich added that she believes there is an opportunity here to build a product for all knowledge workers.