Tech Leadership and Innovation

Stack Overflow CEO sets sights on a billion-user opportunity

Prashanth Chandrasekar, CEO of developers’ favourite Stack Overflow, believes his site can go further.

A businessman using telescope on graph chart. Looking for future company pans

Tech Leadership and Innovation

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Stack Overflow is deeply embedded in the global developer community to the extent that the tagline on its much-visited website has variants of “every developer has a tab open to Stack Overflow”. But its aspirations go even further than the torrent of visits it receives from coders asking questions or sharing expertise. The aspiration: to become another always-open tab on your browser if you’re a technologist, knowledge worker… or maybe even not involved in the digital realm.

But, to begin at the beginning, where is the company now? The numbers are vast, consumer internet-like volumes. It receives over 100 million visits per month and claims to be seen by 80% of developers every week and 50% every day. CEO Prashanth Chandrasekar hails the “network effect” that has seen one question alone (about GitHub since you ask) gain a million views and be upvoted over 40,000 times. It made $40m for the last year in the all-important KPI metric of annual recurring revenue and, 13 years after it was founded, the company remains a big growth story.

That’s thanks in part to Chandrasekar who took the job in October 2019 and helped create a monetisation model that appears to be working. His trick was to rationalise revenue streams down to a premium Stack Overflow for Teams SaaS and context-sensitive advertising. 

Chandrasekar also oversaw last June’s $1.8bn sale of the company to Prosus, a technology investment group primarily focused on the consumer internet and with an interest in education technology. That move has created a buffer for Stack Overflow to invest in the future and its invaluable community.

“Community is at our centre and we’re investing in both the free and paid community,” says Chandrasekar, a former software engineer, investment banker and Rackspace executive. Doing so involves creative ways from gamification upwards to keep them engaged and enthused; it also means walking a fine line between ads that are welcome and those that are irrelevant and/or intrusive. Hence the no video ad rule but if an expert contributor on Lamda gets alerted to a Lamda role, that works well for all concerned, Chandrasekar says. “We want to keep developers and technologists ‘in the flow’ and we never want them to be distracted by an email or a Slack message,” he adds.

Chandrasekar’s vision of Stack Overflow is that this is a company that provides the “context for the code”. He sees his firm offering highly reliable and precise answers to difficult coding questions: a very different world to the wikis he often derides. “Our algorithm has premium on accuracy,” he says. “It’s not a random forum where someone has an opinion on something.”

He also makes a “peanut butter and jelly” comparison between his firm and GitHub, which is the code repository and, speaking of GitHub, we discuss the success of Satya Nadella who, as Microsoft CEO, acquired the company.

“It’s not easy to move a ship of that size,” Chandrasekar notes admiringly, and we agree that it’s interesting that Nadella paints the Redmond behemoth as a developer-centric company. Did Nadella also try to buy Stack Overflow? Chandrasekar declines to answer.

He’s not so shy on the possibility of taking Stack Overflow public one day, however. Although the sale to Prosus means there’s no rush, an IPO would appeal for all the usual reasons of generating awareness, employee equity and so on. “It’s always an option … we’ve always thought about that,” Chandrasekar says.

What about a sideways move into EdTech? Would it make sense for Stack Overflow to become a MOOC, say?

“My belief is companies should focus on what they’re good at,” he says, but he adds that being a best-of-breed doesn’t preclude cutting deals with online academies and an announcement will follow. He hints at further “synchronous and asynchronous collaborations”.

Ultimately, I suggest, Stack Overflow is an example of a niche market winner that can be highly influential but is gated from the off. He demurs, however, saying that while today’s concentric circles may cover developers, technologists and knowledge workers, ultimately there’s scope for answering broader, non-techie questions such as those concerning HR, time off and other daily requests. That could take the company eventually to “one billion users over time” or one in eight of the world’s population.

“There’s a tremendous network effect … there’s a virality in sharing information that’s accurate,” he says, noting examples of where Stack Overflow for Teams is already leaking into non-dev questions.

Yet another advance is in subcommittees the company calls Collectives. These are walled gardens where specialists in a company or technology can create areas of specialisation.

Stack Overflow’s power also gives it a panoramic view based on the survey responses it gleans. The US accounts for 30% of its current audience, followed by India, the UK and Germany. He’s interested to see lower ages in developing countries. “I learned to write my first line of code at 13 or 14 but people are now saying they learned at 10,” he notes. Another vast shift: there seems to be a massive swing towards freelancing with the numbers moving from 9.5% to over 16.5% in just a couple of years.

He’s also seeing a move away from the classic metro locations to smaller cities and towns, the coast and country and he doesn’t buy the notion that eventually we’ll slide back into old habits; not in IT with its 300,000 open jobs postings leaving a buyer’s market for the technically skilled.

But he admits to D&I challenges too, such as the overtly male preponderance among developers and hence Stack Overflow’s community. “It’s a focus for us to make our community look like what the world looks like. We’ve made progress but there’s still a difference…”

He also wants to make Stack Overflow a place that’s friendly and amenable: a Machine Learning “unfriendly robot” is being deployed to remove “acerbic comments”. It’s a tricky line to walk again though because as Chandrasekar notes “an unspecific engineer is probably a bad engineer”.

So Prashanth Chandrasekar has a lot of work on his hands as the context to become the next golden browser tabs warms up yet again.