Prashanth Chandrasekar on writing the script of the future

In the latest Inside Intercom episode we chat to Stack Overflow’s CEO about how their communities are shaping the world.

At this point, it’s clear that Marc Andreessen was entirely accurate with his now famous quote. But that sort of transformation doesn’t just happen on its own – it is the culmination of the tireless work and effort of millions of engineers and developers, building new things and overwriting old tools.

If there is one place where these countless makers gather as a modern community, it is Stack Overflow. Created in 2008 as a question and answer site by Jeff Atwood and Joel Spolsky, it has grown to become one of the primary technology communities on the web, and by far the largest corner of the Stack Exchange Network of sites, which collectively has more than 120 million monthly users.

Our Director of Engineering Jordan Neill spoke with CEO Prashanth Chandrasekar , who took the reins at Stack Overflow in October 2019, about his vision for the community of builders he says are helping to write the script of the future.

Our conversation with Prashanth covers some great topics including why community is at the very heart of what Stack Overflow is doing and how they balance the needs of the product and the community that use it. If you’re short on time, here’s some quick takeaways:

1. Prashanth talks us through his early years in Silicon Valley and how he has transitioned to straddle the product and business sides of the tech industry.
2. With over 120 million monthly users across their suite of sites it’s no surprise that community is at the core of what Stack Overflow do.
3. With such a big community it’s important to balance the needs of the product with those who use it.
4. Prashanth believes that through their work connecting technologists, developers and programmers they are helping write the script of the future.
5. As a company like Stack Overflow grows it’s important to make sure you continue to build with your community and not for it.

If you enjoy the conversation, check out more episodes of our podcast. You can subscribe on iTunes, stream on Spotify or grab the RSS feed in your player of choice. What follows is a lightly edited transcript of the episode.

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Growing up in India’s Silicon City

Jordan: We’re so delighted to have you on the show, Prashanth. Let’s start at the beginning: You wrote your first line of code when you were a teenager, and you’ve said that technology has been part of your DNA for the longest time. Can you give us a brief overview of your background?

Prashanth: Thank you, Jordan. I appreciate you having me on this podcast, and I’m really a big fan of Intercom. It’s a great company and a great product. I was born and brought up in Bangalore, India, which is called the Silicon City of the world, or at least to India-servicing the world, maybe. And in many ways, that has been part of my thought process and upbringing and my education. It was part of the early phase where India became a software powerhouse, helping the world all around accelerate their technology roadmaps. 

A lot of my education early on was either through informal methods, from something as simple as my Dad getting me my first computer when I was very young to learning to code in Logo and Basic and C++ and so on. Then ultimately when I came to the US for college, I studied computer engineering. It was basically a blend of computer science and electrical engineering, which is quite fascinating in the context of today’s IoT conversation. I continued that journey with more software programming languages like Pearl and Java and so on. I also worked at a couple of companies where I was a software developer. So, that’s always been the foundation through which I learned. And I’m very grateful for the problem-solving orientation of that education, both formal and informal. 

Over the years after that, I’ve transitioned to be somebody who straddles the product side and the business side and technology side. I have always had technology as the underlying theme, whether that’s learning about technology companies in the context of consulting or financial services. Or operating in one like Rackspace, where I was right before Stack Overflow. I would say technology has been a huge influence in general to me, but in a broader sense it’s obviously a huge, huge driver of progress in this next big era of ours.

Jordan: That’s great. And you’ve been the CEO of Stack Overflow since October of last year. How have you approached the role?

Prashanth: Stack Overflow is just an iconic SaaS brand with such a fantastic mission that has such a broad impact around the world, right?

Jordan: Absolutely.

“We like to say that we’re the life force of the internet behind the scenes”

Prashanth: Something like 120 million people show up to our websites every month, and that’s certainly not an insignificant number. The impact that we create around the world is just absolutely fascinating – and it’s one I couldn’t pass up when I was approached about this role when I was at Rackspace. And all my teams at Rackspace were always huge fans of Stack Overflow, because of all the engineering teams and the product teams and so on. And everybody benefits so massively in terms of acceleration of their projects and their code writing.

The role has been really phenomenal. The impact that we drive is a big part of why I’ve joined here. It’s great to be able to transform this company now to this next era of its evolution as it creates the next generation of products and solutions for our core customers, who are effectively developers and technologists. Everything we do is in service of them, and all the products that we’re building are in service of them. So it was really about how to build a sustainable company and a product that’s focused on those things and to make sure that the future of this company is even greater than it is today.

Jordan: It seems like Stack Overflow is ingrained into the engineering culture across the world. Being a fan and being familiar with the product and the community, how did that influence your decision in taking on the CEO position?

Prashanth: Yeah, there are only a few companies, if you think about it, that have that much of an impact. Marc Andreessen is an investor of ours, and he talks about how software is eating the world. He’s been saying that for a while, and that’s absolutely true, right? There’s not an industry that you can think of where that is not the case. Everything has an element of digitization. You hear this in the buzzword of digital transformation, and that’s very true. And as a result of that, if you think about who’s actually doing the work to make that happen, they’re effectively software developers and technologists who are in the trenches writing code, influencing what technologies to pick – whether that’s cloud technologies like Amazon Web Services or Microsoft Azure or Google Cloud – and then building the various piece parts to go build out very customer-centric applications.

I can’t think of any company beyond Stack and maybe a couple more that operate as core parts of the ecosystem that drive the statement that “software is eating the world” in a very productive way. We like to say that we’re the life force of the internet behind the scenes. You know, we don’t get the credit as much publicly. But we’re heavily used on a daily basis by developers and engineers and so on. So, that’s really why, being a fan of the impact of the company, it just felt too compelling of an opportunity for me to not pass up.

Community at the core

Jordan: You talked about Stack Overflow having 51 million monthly visitors. 

Prashanth: Yeah. It’s 50 million users monthly users on Stack Overflow and 120 million users every month across all our other Stack Exchange websites and Stack Overflow. That includes our technical sites like Server Fault and DevOps and so on. So, it’s really 120 million. And then the core Stack Overflow website is 50 million.

Jordan: Wow, that’s even more than I had in my head. How is it leading a company where the community is presumably as important to you as the product itself?

“For us to be able to think about the future of this company, it’s very important to think about the community at the heart of the company”

Prashanth: This is an important question you’re asking. After a lot of discussions, when I joined the company I spent a bunch of time talking to every single Stacker, as we call them, or an employee in our company. I talked to a whole bunch of community members, talked to a whole bunch of paying customers of ours. And ultimately the conclusion that I came to was that, for us to be able to think about the future of this company, it’s very important to think about the community at the heart of the company. It is truly the heart of the company. We wouldn’t be the company we are or the organization we are without the community. That’s a core part of who we are, and then there is an ecosystem of communities plus products.

So we actually very much think about the community as part of the product value-proposition of the company. If you think about it, the community is the first product that the company launched, right? Meaning the infrastructure or the community platform where the community can actually interact and rule and all of those things. It is very much a product.

And we have really thought about that very deeply to say, “How do we really treat it as where you treat any other SaaS company?” You have a roadmap, you listen to customers, you iterate on that roadmap and you take feedback from multiple different dimensions – and then you keep building in response to feedback. You do that very rapidly, and you do that with very highly iterative cycles. And so that’s really the approach we’ve taken to the community as well. We think of ourselves as a product-led company and the community is definitely a component of that notion of the company. And again, we’re creating an ecosystem of various communities, whether they’re specific to any of the technical sites that we have.

“Companies benefit on the flip side because they have happy employees, and they are able to attract great talent”

Then of course, there are other products we are building in the service of developers and technologists, whether they’re talent products to help them get jobs. Companies benefit by being able to attract great talent, and then ads help developers get exposed to developer-centric products, which allows them to collaborate very rapidly within companies using the same format and methodology as a public Q&A website. And again, companies benefit on the flip side because they have happy employees, and they are able to attract great talent.

Jordan: And how is the Stacker version of community different from other communities – and maybe even different from the other SaaS industry insights – you have?

Prashanth: The first part of that question is the logic and the brilliance of the algorithm and the actual [product] the original founders, Joel Spolsky and Jeff Atwood, created. That has persisted for 12 years. It’s not perfect, but at the same time, it is quite brilliant in that it has sustained a great system of making sure that you have great and always correct answers up top, where people are able to answer questions, in a very high-impact way. The methodology of using upvotes and downvotes and badges – and making an ecosystem of those capabilities – is very, very unique.

Other communities have forums, and they share content and all those sorts of things – and there are so many different examples of both success stories and failure stories. But for us, we’ve been very fortunate that the system that was put into place by the founders has been everlasting. It is proving to be very, very useful. And that’s really what drives the ecosystem.

And Stack Exchange is very much an extension of the same thing in many ways. It’s a little bit more conversational versus Stack Overflow, which is very binary in nature, if you will. Zero, one. But that ethos is carried all the way through to the other websites. And even if you take nontechnical websites like the Workplace as an example – which is one of our communities about how we help new people enter the workplace and how they can navigate various careers challenges or things they encounter at work – there is still the basic ethos of what I described around the voting system and what they believe is the right answer. But of course there’s a level of discretion and judgment associated with that. But the rule set makes sure it’s objective and that the right questions are asked and that specific answers are provided to persist across these websites.

Product-led vs. community-led

Jordan: And how much of this is the products guiding this versus the community guiding this? I’m thinking of your team’s products and how you ensure that that works even in a private community.

Prashanth: It goes back to my earlier point about how we very much think about the community platform. You’re creating the Q&A platform plus the terms of how we want to govern the community or how the community governs itself. The moderator councils and all the other elements that we’ve got in place are a huge part about building what the community looks like. We’re not building for the community, we’re building it with the community. So it’s a very core principle for us that the community has to have the ability to define in many ways what this looks like, so that they build it along with our help and where we’re very much hand-in-hand with them as part of that.

“We’re not building for the community, we’re building it with the community”

Obviously there’s a core thesis and core brilliance associated with the system that I described earlier from the founders. But that’s been informed over the years by community members by what we call meta users. And the meta community was a huge part in originally helping define this and over the years has been a huge influence on driving the creation of this. And then more recently since I’ve come on board, we have really tried to reignite our conversation in a positive way with the meta community to really include them back into the feedback loops, to make sure that we continue to progress the logic in the community and how we build this in the future.

That extends to private teams, because a lot of the consumers of private teams are going to be the members of the community that are sitting within companies that have loved the external public community model. And there are many nuances of the private experience that they help define through the same feedback loops we have established now on the private side. On the public side, it’s the meta community and other broader feedback loops. Specifically, it’s what we call actually “The Loop”, which is a large-scale survey that we run. But internally, we also do things like customer-value boards and other things along with the people that are using on the private side.

Helping write the script of the future

Jordan: You talk about governance. Do you see the community and product as distinct entities that require different types of management or as complementary halves of the same coin?

Prashanth: The ways in which we work with the community and the ways we want to deliver on commitments are very similar to how we think about bordering on commitments to customers on our products. That’s why we’ve thought very much about the community platform, the Q&A platform that we built over the years as very much a core product. By taking a product orientation to the community, we’re able to really hold true to commitments. I publicly publish a roadmap as an example, and I make sure that people know what the commitments are, and then we hold ourselves accountable to that roadmap.

And that roadmap is informed based on active conversations with a core group of community members – in this case, the meta community. Since I’ve come on board, we’ve done a huge push to make sure that we reengage the meta community, which in transparency over the past couple of years has not been as engaged. We have not been as engaged in that community as we would love to have been. So now we have reignited that in a positive way, and we hope that that continues. And that allows us to have a great feedback mechanism and really help build the community with the community. And it’s never disconnected with the actual requirements.

“By taking a product orientation to the community, we’re able to really hold true to commitments”

Jordan:That’s great. You talked about publishing a roadmap. How do you think about the evolution of software flow in the future? It’s so ingrained in our culture that I don’t see it going anywhere, but how do you make sure that it doesn’t become like MySpace or Bebo and run out of steam as a community?

Prashanth: It relates to our mission and our long-term vision for this company. Ultimately, the mission for us is, “Helping write the script of the future by serving developers and technologists.” And that’s very much my earlier point around us being the life force of the internet behind the scenes. Everybody is writing code for their companies and their particular industries that are disrupting the incumbents in their spaces or trying to be more relevant in the context of the future.

That is an extremely compelling mission that gets us all up and charged up every morning. So we’re very much a mission-driven company from that standpoint. Now, your question around the sustainability of what we’re doing – and how do we make sure that Stack Overflow is an everlasting entity – relates to a long-term vision of the company. The vision for the company is very much to be the most trusted and leading ecosystem of communities and products that help both developers and technologists to solve the really, really complex problems they have – and to be the best place to do that in the world. 

That really fuels us as well in the context of building things every day in the spirit of that statement, and to make sure that the products we build are very relevant and very useful to accelerate developers and technologists. Obviously efficiency is the name of the game there, and people hate being distracted and context switching and not having access to information in real time.

We also want to make companies more competitive as a result of that by allowing them to hire great people, promote their products and ultimately retain their people. Because those – meaning developers, technologists – find their work environment through a product like Teams. It’s highly efficient to collaborate within their company in concert with everything else that they’re doing. So that’s really in my mind, Jordan, how we’re thinking about a very long-term sustainable path for Stack Overflow.

Building with – not for – community

Jordan: Cool. At a community-oriented company like Stack Overflow, there can be a tension between the company leadership and the community. In some senses, both can lay claim to an ownership. What’s your thinking on that tension?

Prashanth: This is my earlier point that we never want to build for the community. We are always building with the community. Over the past couple of years, I think we would admit that the company hasn’t stayed as close to our original power user base or specifically the meta community. So what we have done over the past six months is really try to reestablish a high level of trust and then a foundation for feedback and a foundation for conversation.

We’ve done a lot of different things on this topic. We brought on a new Chief Product Officer on my team who is a direct leader and a direct report of mine. Her name’s Teresa Dietrich, and she is responsible for the community. She sits on the senior leadership team, directly reporting into me. So the community is very much a day-to-day conversation in our hallways, and now I suppose, in our Zoom rooms. But in general, it’s very much a core part of how we operate.

As we ingrain the conversation, and as we work with the community, we’ve had so many conversations with the various community members and groups or individual settings to make sure they very much are building this with us, versus being disconnected. I’m optimistic that the progress we’ve made just in a very short period of time will continue, and we will not find that bifurcation. It’ll very much be a joint effort.

“In general, I think community is an underestimated element of how people think about their companies”

Jordan: Thinking about this tremendous and positive impact that Stack Overflow has had on the developer community, what changes can other leaders implement to start to foster a strong community around their own products?

Prashanth: It’s a great question. I was going to speak about this at the SaaStr conference this year, but obviously it got pushed out because of COVID-19. In general, I think community is an underestimated element of how people think about their companies. A lot of people focus on brand, and they focus on products and so on, but the community is such a beautiful element of making sure that you can create something that is so powerful. 

We follow a few different principles: having a shared identity, making sure that people can actually gravitate towards a certain topic, making sure that we have great product feedback loops with the community, making sure there’s a bi-directional framework, making sure that there’s enough of an incentive system so people are able to contribute and get rewarded for those things – and so on.

By establishing a few of those core principles and then ultimately building with the community versus for the community, all those things will allow leaders to establish fairly powerful communities within their own ecosystem products. Most tech companies are building their communities on Stack Overflow, in our public community. Now they’re doing that with internal communities, with our private Stack Overflow Q&A product. 

So other leaders and other companies should really think about community as a core part of their principles and how they think about what’s most important to focus on beyond brand and product and so on.

Jordan: Thanks so much, Prashanth, for joining us on the Inside Intercom and sharing your insights. We’re heavy users of Stack Overflow ourselves, so we’re excited to see how you keep building it. Where can our listeners follow you and keep up with your work?

Prashanth: For Stack Overflow broadly, we have obviously our Twitter handle and we have our LinkedIn handle. Both are @StackOverflow. And then you can find me primarily on LinkedIn under just my name, Prashanth Chandrasekar. I’ve not been a big Twitter user over the years but I do maintain that as well @pchandrasekar. But I would say LinkedIn has been my primary place to communicate on all things.

Jordan: Brilliant. Thank you, Prashanth.

Prashanth: Thank you, Jordan. We appreciate everything you’re doing at Intercom.