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The people who make your apps go to Stack Overflow for answers. Here’s how it works.


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.

Stack Overflow is a highly specialized kind of social network with a really unique business model. So I wanted to talk to CEO Prashanth Chandrasekar 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.

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.

On top of all that, Stack Overflow was acquired in June 2021 by Prosus, a big company that also owns a large stake in the huge Chinese company Tencent. I wanted to know how Prashanth made the decision to sell and what happens next for a tool that so many people depend on to build all the software around us every day.

Prashanth Chandrasekar is the CEO of Stack Overflow. Welcome to Decoder.

Thank you, Nilay. It’s great to be here. I appreciate you having me.

Yeah, I’m excited to talk to you. Stack Overflow is very important to a lot of people in the Decoder audience, so we have a lot of questions. I have the usual Decoder stuff and I also have questions from some engineers I know. There’s a lot to get into. Let’s start with the basics for people who might not know how important Stack Overflow is. What is Stack Overflow and how does it work?

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Stack Overflow is the world’s largest software developer and technologist community. We serve close to 100 million monthly visitors from all around the world, which makes us one of the most popular websites in the world. I think we are at the top 50 of all websites in the world by traffic, which is obviously a great honor. 

The reason why it’s so popular is that it has about 50 million questions and answers on every possible technology topic. Everything from programming languages like Python to scripting languages like JavaScript to cloud technologies like AWS and so on. All of that information has been accessed 50 billion times since our inception back in 2008. That is a public community platform, and of course that is free and available to everybody around the world, and that is how people build software applications these days. Any app that is on your phone, as an example, I’m sure Stack Overflow was leveraged by developers to build those. 

On top of that, obviously we have a SaaS [Software-as-a-Service] business, which is a private version of Stack Overflow that companies use internally to share knowledge and collaborate. As a function of us being a very popular website, we also have a thriving ads business. So that is effectively us in a nutshell.

Just to back up, in the most abstract sense, Stack Overflow is a very specific and very focused internet forum. You also sell the forum software to companies so they can have their own internal version of that forum and you put ads on that forum.

Yes. With the internal version of Stack Overflow, we like to think of ourselves as more than a forum because this is more of a knowledge base. It originally started out as a Q&A platform, but now has all sorts of other form factors, longer-form content like articles, et cetera, which is why I don’t think we use that term in particular. 

Stack Overflow for Teams, which is our SaaS product, is leveraged by over 15,000 organizations around the world at a very large scale. Microsoft as an example, has 100,000 employees on our SaaS product, where various employees across the company are collaborating and sharing knowledge using the exact same format that those folks have been using for literally over a decade. There is high familiarity. 

The problem of sharing knowledge with the companies has long been unsolved because the information is just floating around in wikis and so on, and is often out of date. With Stack Overflow for Teams, you have this format that is like a self-driving mechanism with up-votes, down-votes, badges, et cetera, which really allows you to recognize your subject matter experts, prompt users to update information, keep content health really high, and reuse the knowledge within your company. All of that is in the SaaS Stack Overflow for Teams. On our public platform, we have a series of advertising-focused products as I referenced previously.

Is the SaaS business the main revenue driver or is the ads business the main revenue driver?

The SaaS business has now become the primary revenue driver of the company. In fact, when I joined the company as the CEO back in 2019, that wasn’t the case. It was still very early in its inception. Folks that approached me indicated it was a great product-market fit. There seems to be a real interest from large companies that want to leverage this capability, but Stack Overflow was a lot more focused on things like advertising and even talent and job listings back when I joined the company. 

Over the past three years, we have significantly transformed the company to very specifically focus on building out a high-growth SaaS business, all the components that you need in a SaaS business, all the product-led motions, the customer success organizations, the sales development functions, and of course having go-to-market resources join us from many popular SaaS companies from all around the world. So I think we have built a great leadership team, and a great team of really great builders who want to build on this great opportunity as we serve technologists and developers.

Can I ask you a question that I have always wanted to ask the CEO of a SaaS business?

You sell your software to Microsoft on a per-seat basis — and I imagine you use Microsoft Teams or Microsoft software. That is also a SaaS business, and they sell it back to you on a per-seat basis. Does it ever just even out?

Does that money all just go in a circle, where you license them Stack Overflow on a per-seat basis and they sell you Microsoft Teams on a per-seat basis, and that’s just net zero? It feels like a lot of the money in SaaS just goes in a circle.

That is an interesting point. I would say what’s interesting about our business is that the problem that we’re solving is well beyond just the SaaS industry.

No, but with Microsoft specifically, does it even out?

We have a very deep relationship with Microsoft, because we are one of the largest — if not the largest — .NET implementations. The entirety of Stack Overflow is built on the .NET stack. We have been working with them for a long time. We are on the Azure platform as an example. We leverage Microsoft Teams for our customers, as most of our customers use either Microsoft Teams or Slack to integrate with Stack Overflow for Teams. Of course, they are customers of ours in the context of Stack Overflow for Teams and they also advertise heavily on our platform. 

On a net basis, I am not sure if it’s dollar-in-dollar-out, if it is exactly the same number, or who has the better “deal” on that. Generally speaking, though, if you think about our largest verticals — and I mentioned earlier we have 15,000 organizations in our SaaS business — a large chunk of that has to do with financial services companies. Obviously there are technology companies in there, but not every company is a SaaS business. These are companies looking to transform, to solve some really big challenges such as hiring, reskilling, and onboarding technologists, as well as driving these large transformations within their companies, like cloud transformations or data transformations. 

Then of course they are trying to do all of this in a distributed work environment all around the world, with remote and hybrid being the new normal. Those are the problems that we are solving. In fact, I would almost say SaaS companies are not the majority of our customers, because those folks are a little bit further down the line of adopting the latest of the tech stack anyways.

I was just wondering, especially with SaaS businesses that require other SaaS businesses to operate. It feels like we are just at a net zero cost all the time as the whole world goes to SaaS. Every time I get a SaaS CEO, I’m dying to ask this question.

Also, to just quickly add, I think there is probably a core set of tools that every company needs to keep their businesses running, operational, high-scale, and so on. We evaluate that literally every year. We look at what we have inside our company, what we need, and we always talk about being very thoughtful about cost and so on. There is a default next-generation tech stack that has formed. I talk about this all the time. You have cloud platform, you have CI/CD tooling, you have collaboration. 

This conversation is a real-time synchronous conversation, but you also have asynchronous tools like Stack Overflow for Teams. Then you have design tools and so on and so forth. There’s a very specific number.

There are thousands of SaaS companies, but we use maybe 25 or 30 tools. That is a very small subset of the ecosystem.

There are probably thousands of SaaS companies, but we probably use maybe 25, 30 tools very heavily across our functions. That is a very small subset of the ecosystem.

Let’s talk about Stack Overflow, the company, and then I want to talk about where you’re going and how you might grow it. Stack Overflow is a really interesting company. It has these deep internet community roots, and it was effectively started by the community of its two founders. Then it took on investment and it grew. Last year, the whole company was acquired by Prosus, another giant company. You have only been the CEO since 2019, which I guess is still three years ago, but that is reasonably new in the long journey of Stack Overflow. What kind of company is Stack Overflow now? What kind of company did you join and what have you been trying to make it into?

When I joined the company, it had this amazing community and public platform that it was primarily known for. It had a series of products that had gotten it to where it was in 2019, namely the talent job listings product and the ads business, which is obvious because we are a popular website. Then of course it had a very nascent, early SaaS business with Stack Overflow for Teams. 

Back then, the notion when the company first started was that it was very much a place for people to solve a common large problem, which is access to information around technology. It clearly became the world’s largest knowledge base over a decade or so. Beyond that, what we really believe is that there is an element of taking all that knowledge and really driving a sense of learning for technologists and developers. That’s really where we are going.

We want to be the destination for technologists and developers, whether they are current technologists and developers or the next generation. That is our vision for our company. That means opening the aperture to onboard folks, very young folks even, from all around the world. We want them to be able to leverage the platform early, to start building technology applications, on-ramping very rapidly, and learning continuously. 70 percent of developers are learning a new language every year and everybody is learning online. 

Our goal is to make sure that learning is a core theme in how we approach our company in the context of all our products, whether that is through our public platform or Stack Overflow for Teams.Obviously through knowledge-sharing and breaking down silos within companies, we are promoting ongoing learning from each other within the organization. Through our employee branding product, we help technologists engage with companies to learn who is hiring, that way they can go and apply for those jobs. 

Then through our advertising products, especially through something like our Collectives product, we are connecting companies, developers, and technologists a lot more closely together so they have community-curated content that is relevant for very specific topics. 

Let’s use Google Cloud for example. The community can very neatly engage with product folks at Google Cloud, get endorsed answers for their questions, and be recognized as the world’s best Google Cloud developer within that subcommunity. Our job is to make sure we promote this sense of learning — and learning starts with a question, as we like to say. We are the workflow folks, in that we are enabling just-in-time learning when people truly have an issue and want to get unstuck through Stack Overflow.

I’m going to come back to that because that is a big vision and there are a lot of pieces to it, but I want to stay on what I call the Decoder questions for just a minute here. How many people work at Stack Overflow?

We are approaching about 525 or so. We are headquartered in New York, and our European headquarters is in London. Then we have folks literally all around the world in every possible country you can imagine.

You said that Stack Overflow doubled its headcount earlier this year and you are now up to 525. It sounds like Big Tech has slowed hiring, so there is a lot of talent out there. How have you decided where to put those additional folks?

We are very much in an investment cycle. You mentioned earlier that we were acquired by Prosus last year, a phenomenal partner and investor with a very long-term view. We really believe that we are only scratching the surface of what is possible in terms of our impact in the world. We obviously have a phenomenal foundation over the past decade. 

The folks that we are hiring from all sorts of great companies are approaching us because they are hearing about our growth story and how we are building a great public platform and community set of products, as well as our SaaS business. Those folks are effectively coming to our R&D organization and product engineering heavily because we are making some fairly large investments there to modernize our platform, to really make sure we respond to community feedback on the tooling that they need to take this up a few notches and to also invest in our SaaS business and really listen to user and customer feedback to be truly product-led in our approach. 

That includes not only R&D resources, but of course go-to-market resources all around the world. We are hiring account executives in Europe, Asia-Pacific, and the US very heavily across all segments. Then with that comes customer success and marketing resources as well. It’s literally across go-to-market and product engineering or R&D, which are the core parts of companies.

Is it an even split? By doubling to 500-plus, that is 250, 275 people. Is that an even split of engineering and sales people, or is it mostly sales people?

It’s slightly more on the R&D side because we wanted to make sure that we double down on technology investment during this phase in the investment cycle to build the next generation of products. It’s right over 50 percent, so call it 55/45 between R&D and go-to-market.

Is it the same ratio at the company itself, with mostly engineers and then sales? How is the company itself structured?

I would say it’s very similar. I think our engineer organization is our second-largest organization, and then of course we have the entire product design and our community organization. Don’t forget that we have another element in our company that engages directly with our 100 million monthly visitors. So that is an entirely new team that most companies just don’t even have.

Don’t worry, we are going to get to that team. Almost all the rest of my questions are about that team.

Okay, wonderful. We then have the go-to-market team, which is obviously the largest team because you have sales folks of multiple kinds for all of our products. Then we also have customer success folks and all the supporting cast around that. So that’s the order.

How is it structured? Who reports to you? What are the divisions? How does that work?

I have had the pleasure of building what I believe to be a very strong team over the past three years. I effectively built out a new leadership team after I joined, which was interesting. 

Eighty-five percent of my tenure as the CEO of this company has been 100 percent remote because I joined in late 2019, and the pandemic hit in 2020. The leaders that report to me are the chief product officer, the chief revenue officer, the chief technology officer, the CFO, the chief people officer, the chief legal officer, and the chief marketing officer. Those are all the functions that you can imagine reporting to me. All of them have some amazing backgrounds — they are great leaders, very inspirational folks, and have really worked hard to build Stack into where we are today, so I’m really happy about that.

You have been at a variety of companies and a variety of roles over time. You have been the CEO of Stack Overflow for three years now. This is the Decoder question: How do you make decisions? What is your process?

My process is my own style. I am very accessible as a leader. I am very much on the frontline, constantly talking to our Stackers, employees, and customers on a daily and weekly basis. That gives me a lot of context and confidence that I know what is happening on the ground. I have the ability to actually judge whether or not we need to go down path A or path B.

When I make decisions I am constantly listening to not only my own leadership team — which is also doing very similar things by engaging with their people, talking to customers, and talking to Stackers — but I am also doing tons of skip levels, et cetera, so that I don’t get too far away from the real issues. Oftentimes, when you grow very large, you sort of have a tendency to rely on the layers in between.

With that context, I am ultimately empowering my leaders to have an equivalent voice so that they can actually surface the key issues that they believe are causing us to move faster or grow faster. There’s a very deliberate effort that I conduct every quarter. We do a quarterly offsite and ask them very specific questions. What is working? What is not working? What have we learned? How do we hit our overall objective for the year and what is preventing us? What are the biggest challenges we are going to face? 

Those questions ultimately surface very common themes, none of which should be entirely surprising to me if I have done the diligence of working closely with folks on the ground. That should give me confidence to be able to say, “Okay, this is the right decision.” It’s about trusting the people. It’s extending “smart trust” to my leaders so that they can bring up the issues that they believe we need to solve, but also having the context from my own vantage point to be able to discern what the right path is.

Let’s put that into context for a big decision. You became the CEO and you sold the company. How did you decide to sell the company?

It was interesting. When I joined the company, we were really sort of accelerating our SaaS business both in 2019, 2020. We pivoted away from that old talent, job listings business that I mentioned earlier, as we actually closed that business. That was one of the tougher decisions in the company that I made. 

Then the Teams business really accelerated. That business now has every possible bank on the platform, every tech company that you can imagine, big retail companies, Microsoft, you name it. With all these 15,000 organizations, that momentum attracted a lot of attention. We got a lot of inbounds from folks in the first two years, where people were saying, “Hey, we’re hearing about you from companies that we work with and we would love to figure out how we can invest in you.”

We actually did a Series E investment in the middle of the pandemic, which was done all online with hundreds of Zoom calls. As that progressed and we continued to accelerate our Teams business, as the message continued to resonate across the universe of investors, we had people that approached us as we were evaluating what it meant for us to be a public company in 18 to 24 months. We went down that path of saying, “What does it mean for us to go public in the next couple of years?” We put together a plan, which I obviously shared with the board and in collaboration with my team. 

While that was happening, other folks sort of came along and said, “Listen, what if you had the option to do that, but also spend some time in the context of a private company to continue to accelerate at an even grander scale?” We had our investors who were with us for over a decade, so we had everybody from Union Square Ventures, Spark Capital, Andreessen Horowitz, Index Ventures, and then most recently GIC and Silver Lake Waterman, the pre-IPO fund of Silver Lake. All those folks were in our investor base and we had a very unique opportunity with Prosus, which gives us a ton of optionality. 

We can still go public as a company if we want to, or we can continue to stay private if we want to. They are phenomenal investors in companies like Tencent, a huge company. It made a lot of sense for us to continue to grow rapidly, drive that investment cycle that I explained earlier, and have the ability to mature as a company as we pursue becoming a bigger company and potentially going public.

Should we think about this like a private equity deal? It kind of sounds like the shape of one. A big company comes in, they take over, they cash all the investors out, and then you can either go public or keep growing.

It’s pretty close to private equity, the only difference being different private equity firms have different philosophies. I would characterize Prosus as a really great blend of investors and operators. They are active on both dimensions. As investors they are very smart about how they think long-term. They are huge fans of the community and of things like education technology [edtech], which we are obviously somewhat related to since learning and education technology are part of what we do. 

They are also very shrewd operators, in that they have pattern recognition with companies because a lot of them have operated or worked in larger companies. They aren’t just totally and completely taking a financial lens to the conversation. I appreciate both elements of that, and it is different from traditional private equity in that dimension.

All right. I think I have an understanding of the business, how you got to where you are, and how you make decisions. Let’s get down on the ground. Stack Overflow for most people is expressed as a community-based discussion forum where you ask questions and get answers. That is very simple. The reality of any social software at scale — and you have 100 million people at scale — is that those conversations are very contentious, moderation challenges are everywhere, and communities go through fallow periods and vibrant periods. It is a community that you have to manage. You said you set up a team to do so. Talk to me about that team and why you set up that team.

The heart of the company is the community. We would not be here without the community that we served. That is by far the biggest reason why I joined the company — the impact that we make around the world. That is the reason why most people join Stack Overflow to work for us. It is truly a once-in-a-lifetime opportunity to serve that many people in a positive way. 

With that opportunity comes a lot of responsibility and complexity to get that right. The great thing that we have going at Stack Overflow is that we are a very objective place relative to other social media sites, which are a lot more subjective. People have a lot of opinions about various subjects, whereas here there is typically a right answer and a wrong answer to a technology question. There may be two answers.

I don’t know if that’s 100 percent true. Are you putting a stake in the ground that there is a right answer and a wrong answer to technology questions?

There could be different ways of solving the problem, but it’s on a relative scale that I am really pointing out.

There’s not a right answer and a wrong answer in politics.

On Stack Overflow, when you are talking about Google Cloud services, there is a generally right way and a generally wrong way.

So you’re saying on the spectrum that you are closer to objectivity.

That is correct. I’m not saying we are not exposed to some of the things that plague large community websites, which I will get to here in a second. But, it was the brilliance of our founders back in 2008 that set this framework up. They set up a rule set which actually established things like, “This is the way in which you ask a great question.” 

“My own experience in Stack Overflow when I first joined was actually a fairly harsh one.”

In fact, my own experience in Stack Overflow when I first joined was actually a fairly harsh one. When I asked a question, I got slapped on the wrist for asking a question that was not perfectly worded. That was a realization for me. I am not a novice user — I learned to build software and started writing code as a 12-year-old when my dad got me a computer from Hong Kong. In that context, it was sort of a jarring experience, but I realized that was the trade-off the founders made to establish this as a very objective place. 

Now, to get to your point around the team, there is a very specific team in terms of community moderation. In addition to that, we have a product team that focuses purely on community products. Those folks build the tools and the automation to make sure that the experience on the public platform is really great. A lot of things we are doing on the subject are like, “How do we make sure that our platform’s a lot more inclusive and welcoming for the next generation of diverse technologists from all around the world?”

As an example, we are rolling out something called Staging Ground, which is almost the equivalent of a shallow swimming pool. People get the opportunity to not get slapped on the wrist like I did a few years ago. They get to ask questions, make mistakes, get friendly feedback, and then are able to go into the deep end of the pool of Stack Overflow with the 15 million questions and answers to ask their first question.

Like practice Stack Overflow.

Practice, exactly. That is one example of what we are doing with our inclusive approach. 

We are also doing something called the Unfriendly Robot, which is literally machine learning [ML] technology that skims all the content on Stack Overflow to look for any comments that maybe aren’t appropriate. The intention may have been to get it right, but if it came across as fairly harsh, then Unfriendly Robot goes in, skims based on patterns, and flags that to both the moderator community as well as the companies so that we can go remediate those and make sure people are appropriately engaging on the platform. Those are two specific examples where we are doing that. 

Within our Stack Overflow Teams product, we have completely removed the ability for people to even downvote answers, as an example. With your colleagues, within your company, it is more likely that you don’t want to just downvote your colleagues’ answers. It’s a lot easier to do that on the public internet when you have hundreds of millions of people all around the world. With your teammates, we wanted to make it even more friendly, so we basically only included upvote. 

Those are very specific examples where we have really tried to make sure that Stack is a lot more of an inclusive place, a lot more welcoming of the next generation of technologists, and people feel comfortable to engage on it.

What are the metrics you use to track that? What is the graph that goes up or down that tells you whether things are a success in that area?

Every month we specifically look at the community satisfaction score. That survey goes out to a lot of people in the community. That is one metric we look at. Thankfully, it’s in a very good spot at the moment, thanks to our collective efforts. 

In addition, we also look at moderators’ satisfaction scores, which is a really strong proxy for us for the health of the community. If the moderators — who are these few hundred people that are making sure that the community is really solid — feel like they are being empowered with the tools that they need to succeed and to be able to serve the broader community, then we know we are sort of on the right track. Even that is in a generally very good spot. As I said, the technology investment cycle is to invest into the community to make sure they have the right tools to be able to do their work even more efficiently.

How are those two metrics proxies for, “This is a welcoming place and we are initiating the next generation of technology leaders in an inclusive way”? You can build a very small, closed, homogenous community where everyone is really happy, but that is not telling you whether you are adding people or that you are welcoming to new people.

Great question. Obviously we want to make sure that people responding to our surveys are coming from a cross-sectional group of people that represent truly what the industry should be like, relative to the world. Even beyond those two surveys, we conduct our Stack Overflow developer survey that goes out to the entire millions of people on our public platform. Typically 100,000 people respond to that survey every year. In a very crystal-clear fashion, we ask these questions specifically on things like diversity, equity, inclusion, and belonging, to make sure that we have true representation in our community and the people who are using our public platform reflect the world.

We have a ton of work to do both in terms of our public platform as well as the technology industry at large to increase representation across multiple dimensions when you think about diversity. I think that is an ongoing effort by us to make sure that we are constantly focused on that subject. We have several initiatives that are driving that, but in general, we are looking at demographic data when people respond to our surveys, in addition to looking at just the score at a holistic level.

What are the demographics of the current user base?

The gender distribution between males and females on Stack Overflow, and generally in the technology industry, is low relative to what it should be. Sometimes there is a survey data discrepancy that is interesting with the number of people who actually feel comfortable responding to the surveys and the types of folks who actually contribute and ask questions. There are a lot of people who lurk on Stack Overflow, who get the answers but are not active contributors. 

All our efforts, as I was mentioning earlier, are in the spirit of making sure people feel very comfortable engaging in the community, and that takes some work for sure. I would say that the mix between males and females on Stack Overflow is something we are focused on.

You came into this CEO role during a somewhat contentious time for this community. It seemed like the user base itself needed a culture change, not just the company at large. There was a code of conduct that was announced about a year before you became CEO. Famously it included the line, “Be nice.” It seems like you have left a lot of that behind. You have imposed this new community team and you have made a lot of changes. When you think about the goals you have for the community, my thesis for all large community sites is that in order to grow, you have to moderate more. As you add more and more people, scale demands more and more content moderation. Is that what you are seeing? It sounds like that is what you are having to do in various ways.

You mentioned a few things that I think are important. First thing is that we need to have the right people with the right experience to be able to do this work. We brought on board a really talented chief product and community officer who helped us think through the framework for how we think about the community in the context of our products and how we make sure that there is a unified approach to when we engage with the community. 

It’s not that we have a public resource on one side and a big, bad business on the other side. It’s all in the spirit of the same user. The user is the developer and is the technologist. Everything that we do should be in the spirit of serving that developer and technologist. Communicating that vision to those users and technologists was one of the most important things to disarm people, to say, “Listen, there is not a nefarious agenda focused on this. This is all about serving you.”

Then it’s about bringing on folks for that community team that we have built out very meaningfully. We brought on a very talented person, another VP of the community team. That person joins us from another leading site that does not exactly what we do but very similar to what we do. That has been a huge boost, because again, lessons learned from other companies that have been in the deep end of the ocean around this sort of stuff have been great to make sure that we don’t make the same mistakes over time. 

We spent 2020 and a good chunk of 2021 really stabilizing the community sentiment. To your point, when I joined the company, there was a lot of vocal feedback. I walked into a fairly…

Right. Moderators were quitting.

It was a very controversial time. Through this articulation of the vision, it has taken a while to rebuild trust in many ways, to say this is what our true intention is, by appointing the right people to fulfill promises that we started making. My belief is based on the scores that we have looked at. I am constantly talking to community members all the time and, of course, with our team. We have done that. We want to continue to focus on that. 

Now we are in a phase where it’s not only stabilizing, but we want to really delight our community. It is going from a fairly noisy situation to stabilization to now delighting. Those are the three phases, and we are in the last phase of that. That is to say, how do we make sure that we give our community members all the things that they really need to be able to find this super useful? That is what has led us to our vision of making it the destination for both the current and next generation of developers and technologists. All the things that we want to build are in that spirit. We are going to go well beyond what the site has been over the past 14 years as a Q&A site. We want to be a lot more focused on running all sorts of experiments, including things like edtech content, through some of our partner companies.

If we are actually solving developer problems in the moment, can we not extend that? Can we not extend their learning even beyond that moment of answering a question? Can we provide them with an appropriate course from Udemy, Pluralsight, et cetera? “If you just looked up a question on Amazon Web Services Lambda, here is an advanced AWS serverless course that you can take right after you answer that.” They make a mental note because it’s the best way for them to be prompted to learn, when they are actually in the issue. Those are small examples of saying that we are very much in the delight part of our journey with the community and we really will be taking that up a few notches here.

I feel obligated to say that Prosus has a big stake in Udemy, which was just mentioned. It’s all part of the same conglomerate. Let me ask you just a philosophical question. You said that generally there is a right answer in technology problems. I think there are some people who would just disagree with you flat-out. Maybe I’m not that person. Maybe I don’t have the background to disagree flat-out, but I know people who would flat-out disagree with you on that point.

What you are proposing is almost a philosophy of engineering. You come and ask a question, and then Udemy teaches you something related to your question. You end up with one way of doing things because you are the biggest resource. Philosophically, is that the vision? People enter with questions and then learn how to answer their questions in the deep end of Stack Overflow, which has a very rigid etiquette. Then they get pushed into courses at partner companies that teach everyone how to do things the same way. Is the vision to standardize how things are built like that?

“We are a lot more objective than we are subjective. That’s the point.”

That’s a good question. I want to make sure that I’m clear when I talk about the framework of right and wrong. I’m talking about a super macro level, relative to opinion-based social media sites. That is the point that I was making earlier on. The spectrum is really the point I’m making — we are a lot more objective than we are subjective. That’s the point. 

Now with regards to a public platform, we are not trying to be very draconian like, “Hey, this is the right way to do it and the only standard to do it.” I will give you a very specific example. We have 50 million questions and answers. Community users have the ability to sort the answers they are receiving as part of their search results, in terms of the most voted. Let’s say there is a question asked 10 years ago about JavaScript, where somebody answered and it has been upvoted thousands of times. That can be the answer that they look at, or they can also sort it by what we call trending. That means that it is the more recent way of solving the exact same problem; 10 years later somebody came up with the answer, and that is a much more elegant solution than it was 10 years ago.

We have an entire effort focused on things like outdated answers, to say, “Hey, this answer may still be appropriate, but it’s sort of stuck in circa 2010. But in 2022, this answer is even more elegant and you could solve the problem this way because people have progressed in solving the problem.” 

In that context, there are obviously multiple ways to solve a technology problem. Absolutely, there can be a better, more efficient way. That is human progress. That is why every year we see a new technology language, a programming language, come to the top of the list on our survey. One day it’s Rust, the next day it’s Svelte. If that didn’t exist, what’s the point? 

We want to continue to build on inefficiencies from prior abstractions of programming languages. It could be a memory issue, or it could be the elegance of writing code and how effective and how pithy you can actually make that. All those things are driving people to discover newer, better frameworks and scripting languages that solve previous inefficiencies. That is just technology progress. So for us, we welcome that. We absolutely talk about that. That is very much core to what we do. We encourage that development within the technology universe. Hopefully that answers your question.

It does a little bit. I am interested in how you add members to the Stack Overflow team and to the community team. To understand that there is a new, more modern way to do something in JavaScript requires you to understand it. It’s a community built around very specialized pieces of knowledge. Do you have to hire in those specialized pieces of knowledge? It strikes me that the world’s foremost AI expert probably wants to be writing some AI code as opposed to moderating the AI code that gets posted to Stack Overflow. How do you juggle that? How do you balance that? How do you make that sale?

I think there are three components there. One is the people that work at our company. Then you have the contributors on Stack Overflow who are both the users and the consumers. Then you have the moderators, who are effectively in between the company and the community of consumers and contributors.

Do you pay the moderators?

We do not. They are nominated, voted-in members of the community, and typically they are volunteering to do the role because they understand in many ways that it is going to be a huge public service to move the world forward. 

As for the expertise on AI, it is less important for us to have a moderator that is the expert in AI on the AI Stack Exchange site. I recently met with one of our most prolific Stack Overflow users, Jon Skeet. He has an extremely high number of points. If you look him up, he is in the top couple users. Somebody like him is taking time out of his day to be able to contribute to this community, because that is in the DNA of a developer. We have all been there at 3AM trying to debug code, so we understand the frustration of doing so without any peer help. 

The fact is that you have these experts on Stack Overflow, the world’s best AI developer is on Stack Overflow or the world’s best Google Cloud developer on Stack Overflow. They are the ones making sure that they are helping out their fellow developers and technologists based on their own learnings of struggling through using whatever capability to build things. That is the mechanism. It’s less about us hiring the right experts. We are not meant to be a research house of people. It’s all about the community. The scale that we get is because the experts in our community are able to help each other out, because of that fundamental DNA trait that they have to help each other out.

What is the incentive for the moderators to do all this work? To moderate and deal with other people is very much a social job. It must be exhausting. What is the incentive if you don’t pay for them?

It’s quite intangible, but at the same time it very much pulls on the heart strings of who we are as people. It’s that emotional connection and the gratification you get from literally helping millions of people. We measure that and we tell users, “This question you answered has been accessed millions of times and has solved millions of people’s problems.” That is irreplaceable. You can pay somebody $20 for an answer, but that doesn’t get you very much. I think it pollutes the environment by looking at it from a commercial lens.

The point is that the gratification that developers get by helping people all around the world is the reward and the incentive. They are getting recognized as the expert on whatever subject matter they are focused on, whether that is within the public platform or for Teams, within their company. An introverted engineer sitting in another part of the world is answering all the JavaScript questions within this company. That person was never known to be an expert on JavaScript until Stack Overflow for Teams was able to give that person recognition. That is how they operate. They like to be behind the scenes helping people versus speaking up in meetings. I think that is the biggest motivation for people to have interest and energy to do this.

That is the motivation to contribute. What is the motivation to moderate?

It’s similar in that it keeps the system going. You want to make sure that the algorithms and the principles of the site are being adhered to. You don’t want to make this the Wild Wild West. It has to work. The only way that the “right answer,” despite the earlier conversation, surfaces is by adhering to these principles, so that you are not getting off-putting comments and that people feel welcome. It’s like, “Hey, you are representing this community of 100 million people to make sure that the system is propagating, moving forward, and helping the next generation of developers.” People are going to solve their problems faster and faster. 

They are also the interface with our company to provide us with input and feedback on what we should be building for this next generation of the site. From their standpoint, I think moderators, along with our Meta community, have a phenomenally influential role on Stack Overflow. Meta on Stack Overflow is another really fantastic place for us to engage directly with our power users to get feedback on a lot of things that we are building, or considering building, based on input that we see from our surveys. Those are the motivations.

One of the things I hear from the product people and executives at consumer social networks is that consumer behavior shifts on a dime, and they have to invent new products to capture whatever sharing dynamic might exist today. Instagram has to copy Stories. Stories has to copy TikTok. Everyone has to copy BeReal tomorrow. That is the dynamic of consumer social software.

Mark Zuckerberg famously said something about how there’s one sharing dynamic that takes over for a generation, and they had to go buy that company; that’s why they bought Instagram. They were not able to buy TikTok, and I think they have to furiously compete with TikTok now. Stack Overflow is not that thing. I don’t think Stack Overflow has Stories. I don’t think you are going to turn it into TikTok… Are you going to turn it into TikTok?

No, definitely not. We are going to continue to stay on that objective end of the spectrum.

Do you track the incentives to contribute and the incentives to moderate? Have they changed? It seems like even if the format isn’t changing — it is still mostly text — the incentives and social dynamics of the community definitely change, especially as you scale and try to make it more diverse.

There are obviously a lot of movements these days. If you think about concepts like blockchain or the “Web3” area, a lot of that is based on trying to make sure that people get recognized for the contributions they are making. It could be in the context of a creative individual who has a new song that they created — and of course we can talk all day about that subject. The point is that we are tracking all elements of recognition and what the next generation cares about. What do they find valuable? We are absolutely doing that research.

I think what is fundamental is the characteristics of this population. You said it really well up top. This is a very specific group of people. Technologists and developers are just a very special group. What motivates and drives them is exceptionally different from the general populace of people. I think that is why the incentive system is not a one-size-fits-all where in a very instinctual fashion we layer in some new recognition system. What has been working and the reason it has been working with the network effects that have existed is because of all the things I have mentioned to you. It is part of the DNA and the inherent set of motivations of people in this community. Are we tracking it? Absolutely, because that is just our job. Are we going to make any sort of fell-swoop decisions? No, we will do a lot of research before we go down those paths.

One hundred million people all developing software is not a monolith. You brought up Web3, so I have to ask you about it. Web3 developers or evangelists are one kind of culture. People love it or they hate it; there does not seem to be a back-and-forth. I am assuming Stack Overflow has crypto-related discussions, forums, and questions and answers.

How do you keep that apart? How do you make sure that the community is doing its work without the people dropping in to say they are all stupid or doing scams? You don’t have one community, you have thousands of communities, and that one in particular is contentious, right? It’s controversial. How do you keep those things apart? How do you manage that?

We have close to 170 websites. Beyond StackOverflow.com, we have all these stack exchange websites that include, in that particular topic, everything from Bitcoin to Ethereum to Cardano, and each of those have stack exchanges. There is also a Solana one. All these sorts of topics that have been in the news most recently. Despite what is happening with the crypto universe and the sort of boom and bust, what is very evident from our data is the number of questions. Much like cloud and machine learning, which have gone up by 50 percent year over year in the past decade, blockchain questions and all these related subjects have gone up 80 percent year over year in the past 10 years. 

You are right in that there is a lot of content being generated on Stack Overflow on these subjects, but they are very technology-focused subjects and questions. They’re not opinions about whether we believe this is a trend or not, or any of those sort of subjective conversations that belong on a social site or on TikTok or anywhere else that people are talking about things. They are, “How do you build an application using this new framework?” 

What is so good about the intersection is the fundamental building blocks of a Web3 application are very similar to the fundamental building blocks of a Web2 application. I’m talking about things like Python or Node.js. You can see the data. There is a correlation where we see the number of Python questions go up relative to the number of machine learning questions, for example. 

Similarly with blockchain, there is a correlation. That is how we stay “out of the noisy conversation” about a fairly polarizing environment where people love it or people hate it. We just focus on the technology and if people want to experiment, our job is to enable them to experiment through common knowledge.

Do you have to build different kinds of products for different communities? I just imagine the needs of the Web3 development community or the Solana development community are different from the needs of the Rails development community.

Yes, at some level that is true, but at the level at which we are operating, which is to provide this forum or knowledge base, the fundamental principles and rule sets still apply across these. So we are not really changing the way we do it. If anything, we have heard a little bit more about input from these newer Web3-oriented communities saying they want to be able to engage even more on a real-time basis beyond the asynchronous type of way. That has been interesting feedback. 

They want more around those lines. That is an interesting new piece of input relative to pre-blockchain era, if you will. Other than that, I would say generally speaking the principles apply across the board. 

As I talk to other executives at other community sites, Section 230 comes up over and over again. It is the big looming dark cloud over all internet moderation, over all online speech. Politicians from both parties love to wield this threat of doing something with Section 230 to get the moderation they want. This affects every site with user-generated content. It affects our comment system. It affects all the way up to the scale of Facebook. It must affect Stack Overflow too. Is this something you think about?

It sort of depends on what element of that. Our community guidelines and our licensing basically govern most of what we are doing on the subject. I think that with regards to making sure that there is no inappropriate content on our website, the good news again is that we are on the scale of being objective and subjective. We are in a place of objectivity. The appropriateness of the content is moderated by the community principles and guidelines.

Section 230 is the law that says you are not liable for what your users post in Stack Overflow. If you take 230 away and there is some liability for you for what Stack Overflow users are posting, that could be the end of the business, right? You would now be liable for the code that gets posted to Stack Overflow. Is that something that has caused your general counsel or your policy person to sit down and say, “Look, this law going away could potentially be the end of this business”?

I don’t know if it’s something that we actively discuss as an existential threat to our business. Based on the intention of the users plus the content on our website, it is unlikely for us to have some nefarious activity on our website because this is about the fundamentals of Python, right? How nefarious can that get?

Pretty nefarious, I would think. If I post some malware to Stack Overflow and someone else uses it, I could potentially sue them, but I cannot right now sue you.

Right. I think it is something that we will watch. It’s something for us to pay attention to, but at the same time, given the nature of our website, what we do, what the intention is behind it, and our community guidelines, it’s not something that we feel is going to be a big issue in the near term.

Let’s talk about the content itself. We have talked a lot about moderating the community. What gets posted to Stack Overflow is often code. There are studies saying, “Oh, there are mistakes in the code that ends up in shipping applications. Hey, be careful with Stack Overflow, you don’t want to inherit a mistake that somebody made years ago that you’re just pulling down.” Again, there are studies that say this happens all the time. Do you actually moderate the answers, the code that gets posted, or do you leave that totally to the community?

It’s almost entirely up to the community. The company is constantly making sure that we have the right frameworks, principles, Creative Commons licenses, those sorts of things, to make sure that there is transparency in what people are using, what they are posting, what they are signing up as, and their privacy. We don’t sit and scan people’s code snippets that they are posting on the website. We don’t do that.

Do you think the stakes of that get higher with Web3? There are a lot of scams and a lot of weird exploits in Web3. Do you think the stakes go higher with the money that is flowing through the code that gets posted to Stack Overflow?

In that context, yes. People have a lot to lose in that scenario if they are leveraging something that has nefarious behavior. You have seen examples over the past 18 months where people have been completely smoked out in those scenarios by the community. That is the power of the group, to make sure people don’t take advantage of the situation.

In terms of growth, you have talked about growing, you have talked about the SaaS business growing. The most basic way to think about Stack Overflow is that you ask a question and you get an answer. It works — the communities are there to provide answers. That is why the products are successful. Most people ask questions to Google.

Obviously Google is a client of yours and you have Google-related forums. Does Google take search results away from you? Do you think of them as a gatekeeper or as a partner? It just seems like any place where there are answers to questions is a place that Google might expand its remit to cover.

We think about Google as the fundamental way in which people access Stack Overflow. I think over 90 percent of our usage, maybe slightly even more, comes from somebody going to Google, asking a question. The first answer is typically from Stack Overflow because of the community-voted answer, and then they are showing up at our website, versus people doing it within Stack Overflow’s own search. Now with Stack Overflow for Teams, they are leveraging asking a question within Slack or Microsoft Teams and the answer is going to pop up from Stack Overflow for Teams because it is integrated.

Stack Overflow isn’t the primary point of contact? You either ask Google or you ask some other piece of workplace software.

“Our job is to make sure that we are the system of knowledge.”

That’s correct. Our job is to make sure that we are the system of knowledge. And the system of engagement can be whatever their workflow is. We know that the system of engagement for people generally is that they are in their chat ops software like Slack or Microsoft Teams, or they are going to Google. All arrows point back to Stack Overflow as a source of knowledge. We want to make sure that the information is accurate. How they get to it is… we just want to be in the flow of their work.

 That is why we do not really push back on that or try to change that workflow in any way. We are working on things like, “How do we make that even more simple? How do we remove steps from that to make sure that people have even more instant access to the information at the right place at the right time?” That is why with Stack Overflow for Teams, there is a lot of experimentation around that subject. That is why it integrates with GitHub, Jira, Microsoft Teams, Slack, Okta, and all these other things. And there is a lot more coming.

Is that the safer side of your business, the enterprise side, the SaaS business? Any business — and I will freely admit that this is potentially our business too — where all the users come to you from Google is a business that is at the mercy of Google. It sounds like with the SaaS business, the enterprise business where you are integrated into people’s workflows at work, you have stable revenue and all that stuff, is safer than the public Google-facing business. Is that how you think about it? Do you think Google is going to make a Stack Overflow clone and send all the traffic to that?

I can’t comment on Google’s plans, but I would just say that for us, I don’t know if it’s safer. I would say it’s more that we want to capture all elements of people’s workflows so that they are getting access to Stack Overflow information when they want to access it. We have just kicked off a very large student ambassador program at 250 campuses where we are getting all this feedback from young folks. That is how they access it. They are going to Google, they ask a question, and that is how they get it. We want to be there when they do that. When they graduate from college and they go into companies, we want to make sure they leverage Stack Overflow for Teams. 

Even if they go to Google, most of our customers now have people redirecting their Google searches through a proxy redirect back to Stack Overflow for Teams. Then within that, people are enabling a private and public version of Stack Overflow within their companies, so they have the read-only public version up top and the private Stack Overflow for Teams at the bottom. It’s about not disrupting the workflows. It’s mostly how companies have that within their organizations. And outside, if people use Google, they use Google. We basically want to be wherever people are to give them information.

All right, I have one last big-think question. You have access to all the data and you see where all the heat is. What is the next technology set to explode based on what you are seeing on Stack Overflow?

That’s a loaded question. I would say every year we see the evolution of technologies. If you had asked me this question about a year ago, the proliferation of Web3 technologies on our website was very high, and that hasn’t really stopped. I would say the number of requests coming in for new stack exchanges to be opened up on Stack Overflow were very heavily focused on Web3 in the past couple of years. We saw a lot of proposals. 

In programming languages, it is one of those things where we start out with binary code, with zeros and ones assembly code, and it basically has been abstracting ever since over the multiple years and decades. Every year there is something — as I was mentioning earlier on — that is being compensated for. There is a memory issue or there is elegance, or something else.

Each of these languages are building on each other with higher and higher levels of abstraction, which is why we are now getting much closer to providing people with a lot of elegant ways to solve problems while writing code — even all the way to things like no-code and low-code, where you actually see it is super easy for people to be able to leverage coding in general. I don’t want to provide a specific answer. I just think that every year there is absolutely a new leader making up for the last year’s set of deficiencies.

Last question. This comes from our own engineers at Vox Media. What lessons have you learned about community building and inclusion that other people can use when they are developing communities like this so we don’t make the same mistakes?

It is making sure that there is always a way to make sure you are balanced. The world is not binary. Even though I said there is a right answer and a wrong answer, I think that my own leadership style is non-dualistic in approach. Just because we are an objective website, doesn’t mean that we cannot be inclusive of newer folks looking to ask questions with the right intention. They are just asking a question. They are trying to figure out how to solve their problem, they may not know all the rules, et cetera. There is a way. You have to be deliberate by investing in discovering what the way is. In our case, we have done things like Staging Ground and the Unfriendly Robot to augment that experience to make it possible for folks.

I think it’s appropriate for us to end this discussion by saying that in my own personal philosophy, there aren’t actually just two extreme answers to a problem. The answer is typically always in between or in the middle, so to speak. It’s ironic, me mentioning this as the Stack Overflow CEO, where everything is truly right or wrong. The answer, especially as it relates to humans, is that there is typically no right or wrong answer. It’s typically somewhere in between. That is my approach. I think that if there is feedback coming from users that this is what they specifically need for things like diversity and inclusion, we want to make sure we are absolutely listening to that. We stay flexible with that and we invest in the capabilities to make sure these folks feel a lot more welcome on platforms like ours.

Prashanth, thank you so much for coming on Decoder. We will have to have you back soon.

Thank you, Nilay. I appreciate all your questions.

Decoder /

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