Democratizing Software Development on Stack Overflow with Prashanth Chandrasekar

About Prashanth Chandrasekar

Prashanth Chandrasekar is Chief Executive Officer of Stack Overflow and is responsible for driving Stack Overflow’s overall strategic direction and results. Prashanth is a proven technology executive with extensive experience leading and scaling high growth global organizations. Previously, he served as Senior Vice President & General Manager of Rackspace’s Cloud & Infrastructure Services portfolio of businesses, including the Managed Public Clouds, Private Clouds, Colocation and Managed Security businesses. Before that, Prashanth held a range of senior leadership roles at Rackspace including Senior Vice President & General Manager of Rackspace’s high growth, global business focused on the world's leading Public Clouds including Amazon Web Services (AWS), Microsoft Azure, Google Cloud Platform (GCP) and Alibaba Cloud, which became the fastest growing business in Rackspace’s history. Prior to joining Rackspace, Prashanth was a Vice President at Barclays Investment Bank, focused on providing Strategic and Mergers & Acquisitions (M&A) advice for clients in the Technology, Media and Telecom (TMT) industries. Prashanth was also a Manager at Capgemini Consulting where he managed Operations transformation engagements and consulting teams across the US. He holds an MBA from Harvard Business School, an M.Eng in Engineering Management from Cornell University and a B.S. in Computer Engineering (summa cum laude) from the University of Maine. Prashanth is married and has two children.


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Transcript

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Announcer: Hello, and welcome to Screaming in the Cloud with your host, Cloud Economist Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

Corey: Welcome to Screaming in the Cloud. I'm Corey Quinn. I'm joined this week by relatively recent Stack Overflow CEO, Prashanth Chandrasekar. Prashanth, welcome to the show.

Prashanth: Thank you, Corey, a pleasure to be here. Thank you for having me.

Corey: Your history is fascinating. Before you joined Stack Overflow as the first non-founder CEO, to my understanding, you came out of a relatively lengthy tenure back at Rackspace.

Prashanth: That's right, yeah. So, Rackspace, just a tremendous company and experience, just, I'm so grateful for that as part of my career and, just really having, kind of, worked with a tremendous number of amazing people at the company down in Texas, and around the world. Yeah, so in my journey at Rackspace was all about how do you redefine the company in the context of a fairly competitive landscape in the cloud? If you remember, Rackspace, originally it started in the context of a managed hosting company well before I joined there. 

And when I joined in 2012, we had our own public cloud, the OpenStack Public Cloud, and going head to head against Amazon Web Services, which was our primary competitor, and as we know today, obviously AWS is the leading public cloud capability and still growing. Just a massive, massive success by Andy Jassy and team. And so, back in 2014 or so, our company decided that we wanted to effectively not compete based on infrastructure and just based on a price war, which is obviously going to go to zero, which didn't make any sense. And that—

Corey: Yeah, who could lose money the slowest and be the last person standing.

Prashanth: Yeah, indeed. And then, Amazon being the company that it is relative to Rackspace, it’s relative size, it didn't make a lot of sense for us to compete based on that dimension. So, what we had to do is some soul searching to determine what we were truly good at. And we decided that we were really good at what we call fanatical experience—or fanatical support, what we used to call it back then—and that was all about providing services. And so, that's what we ended up doing, saying why were we so specific about providing services only on our cloud or our infrastructure? Why wouldn't we do it on any kind of infrastructure, much like we would support Linux or Windows, in the operating system context? 

So, that's when we made a strategic decision in the company, one of the most important decisions in the history of the company to support Amazon Web Services, and then soon after, Microsoft Azure, and Google Cloud. And so, that was just a, I would say, a huge pivot for the company. And I was part of the founding team that did that, and then also helped lead that business to a multi-hundred-million-dollar business over the course of just a few years. And that ultimately was called the Managed Public Clouds business at Rackspace. 

And that was, I would say, was a tremendous experience in building something very rapidly, scaling it by rapidly, enabling a lot of people both on the product engineering side plus also the go-to-market side. So, just an all-around, a great experience that I'll never forget.

Corey: Oh, absolutely. It's fascinating talking to you, just because for those who aren't privy to all of the ins and outs of my various career twists and turnings, you and I went to undergrad at the University of Maine in Orono, at the same time. And that is the last time we ever really had anything in common. You wound up graduating summa cum laude with a BS in Computer Engineering. You got a master's in Engineering and Engineering Management from Cornell, and then an MBA from Harvard Business School. 

Whereas I failed out of undergrad, discovered my high school diploma was not accredited, so on paper, I've been walking around with an eighth-grade education that no one can ever take away from me. The path not taken as it were. But you've had a fascinating career trajectory and now have landed as the first non-founder CEO of, whether we think of them as a cloud company or not, I would argue that the cloud would not exist without Stack Overflow in its current form.

Prashanth: Yeah, no, by the way, on the background, yes it's just a fantastic coincidence that we both went to the same undergrad schools. And obviously, listen, everybody has their own path to their own, kind of, finding their own true purpose, and what they end up doing in life. So, nothing's right or wrong. It just happens to be what the paths that we chose. So, I would say, I think that yeah, Stack Overflow throughout my time at Rackspace was just such a loved entity and a loved community. All my technical teams always historically used Stack Overflow. We've always known about it. I’ve known about the company for a long time. And then, more towards the end of my time at Rackspace, I was approached about the role, saying that, “Hey, this great foundation exists.” 

So, this community still has something like 50 million users that come to the website every month, just on Stack Overflow. If you include Stack Exchanges, another 70 million folks that show up at the Stack Exchange websites. That's about 120 million people that show up every month. We have something like 150,000 new signups on Stack Overflow every month. So, this is a tremendous amount of scale at, 12 to 10 years after founding the company. And that foundation is just, I would say, there aren't a lot of companies that actually have that, sort of, a phenomenal foundation. 

And on top of that you had these great products that the company was beginning to build and had built over the past few years. Talent product, which is our job listings product where big companies can post their jobs on our website. And obviously, we have the world's developers on our website, about 25 million, all of them are—they pretty much use Stack Overflow on a daily basis. So, they're able to match jobs and applicants. And then you've got the ads business that basically is an ability for big companies to showcase their developer-centered products. So, think about, for example, in the case of Google Cloud it could be BigQuery, and how ads on that so that developers can leverage the product. 

And then, finally, the latest SAAS product that we have is called Stack Overflow for Teams product, which is just a tremendous way to share knowledge and collaborate within companies across their development teams, their product teams, their security teams, IT teams, etcetera, to make sure that they have the latest and greatest content internally around their feature releases, and code snippets, etcetera, and all be available for Teams like go-to-market teams and other teams that need to be very close to the core information. And that product has really been a tremendous growth engine for Stack Overflow. So, we've seen that business double year over year. And we've got companies like Microsoft that have something like 70,000 users on Stack Overflow for Teams. 

So, that whole story and why Stack Overflow it’s kind of an inflection point in its history. It's helped build the cloud, to your point, by enabling developers around the world to really rapidly build out capabilities across AWS, Azure, and Google, but also now helping them become even more efficient as part of their development workflow, and adding value like in helping them find jobs and awareness about various products. So hopefully, that's a helpful overview for you.

Corey: Oh, it absolutely is. It's always interesting when you see a company that is effectively a household brand has a management or leadership shakeup in different ways. For example, when Google acquires something and the immediate knee jerk reaction is oh, no, they're going to kill it. When Stack Overflow effectively changed leadership, it was—the biggest reaction I had, as a full Stack Overflow developer myself is, “Oh my God, there might turn off copy and pasting, and then where will I be?” So, just for the record, there is no current plan to disable copying and pasting on Stack Overflow, Stack Exchange, or any of the affiliated halo sites.

Prashanth: Oh, my goodness, no. I think that we want to do more things for our community, not less things, and we want to make life easier for our community members versus the opposite, so absolutely not. And so, just if you think about a lot of what we're planning on doing this year, one of our top priorities is community engagement and inclusion. So, we really are trying to make sure that we get more and more developers, and hobbyists, etcetera, and people are writing code earlier and earlier in their lives. 

We were trying to make sure that they feel extremely welcome to leverage the community, to utilize the resources there. How do we have even more productive ways to intersect our public community Q&A platform and our private Stack Overflow for Teams product, so that there's even more developer workflow integration, so people don't context-switch, etcetera. All those things are in the spirit of making sure that life is easier for community members like you. Because today, most people like you go to Google, type in a question about, whatever, could be a Python question, or Amazon Web Services question, and you land on Stack Overflow—

Corey: Or copy and paste an error message directly in and cut out the middle person. For whatever reason, that seems to be a less common approach than it really should be, given how many problems it seems to solve for.

Prashanth: Exactly, yeah, so that happens more often than not. And we just believe that it should be a lot more seamless of an experience for users like you. And that's why we're integrating in the community we integrated with GitHub last year. For our Stack Overflow for Team product, we have integrated with Slack and Microsoft Teams, and we're about to announce our integration with JIRA and GitHub Enterprise. So, there's just a lot that we're hoping to do to make sure that the developer workflow is highly integrated, and ultimately, we’re indispensable as part of that.

Corey: I would say that, for better or worse, whether or not companies know that they're dependent upon Stack Overflow, they absolutely are, in that it is saved so many person-years of time, in the past decade or so—however long it has been in business, it feels like forever, but I understand that it's not the awareness of the passing of time is a slippery thing—but it has been a transformative place to solve things. I mean, I will say that I've dabbled a little bit as a part of the community and found it wasn't really for me, and for the best of all reasons, namely that giving an answer should not be a facile one- or two-line response. There's expected to be some depth, and some exposition, and explaining not just what the right answer is, but why it's the right answer. And when I'm trying to do this late at night, from a phone in a hurry, that doesn't really lend itself to the same thing. I mean, I rarely have the attention span to finish writing a complete tweet, let alone a full deep technical dive into something. So, that high community standard is absolutely one of the differentiating virtues of the entire community.

Prashanth: Yeah, no, spot-on on that. There is a very—you've got to give up to founders just a tremendous amount of credit. Both Joel and Jeff Atwood have built this system that is sustained for so long, and despite what could be perceived maybe harsh realities of downvotes or, kind of like, a very binary experience or a very specific experience, it works. It just works. And that's the whole point of it is to make sure that people get the right answer very quickly, and they're on their way. And that does come with some downsides with regards to, sort of, the friendliness element and with, if you're a newcomer, you might feel—may not be, kind of like, the easiest way for you to get going. 

I remember when I was dabbling myself in the community, even before I joined the company, I would say, it was, sort of, a harsh reality of actually participating as a brand new member. It's not the easiest way to get started. So, we are testing and iterating on several ways to make sure that we are a lot more welcoming, and making sure that people don't feel intimidated. One of the more recent things we've done is actually make sure that people asking great questions also get as many points relative to answering questions. And then, we also are making sure that we remove negative comments and we've actually made some tremendous progress over the past quarter on that. Almost half the negative comments relative to the prior period of measurement. So, we are doing many things to make sure that, despite the very objective binary kind of system that's in place, we are making sure that we are making it more welcoming for new users.

Corey: You've also made significant changes in the past year around how you're handling diversity conversations, representation from different groups in the community. And what’s, I guess, fascinating to me is how public you've been about some of this. It hasn't been something that you give lip service to it once a year, and then it vanishes. We're starting to actively see changes in the community happening and percolating out. You haven't been trumpeting it from the rooftops, but you also haven't been secret about it or working non-transparently to get there. It's fascinating and I'm curious as to how that's, I guess, how that came to be, and how we can start seeing that in more companies.

Prashanth: Yeah, no, I think, we just believe that Stack Overflow, given, kind of like, the level of influence that we have around the world, we are very much a platform, a community platform that represents our users, the user base across the world. So, the world's developers leverage our platform, but we have a long way to go in terms of even making sure that everybody signs up for an account and is active, etcetera. So, there's going to be work to do, and part of when we do our developer survey, for example, a yearly developer survey, it's just very, very interesting for us to see some of the results there. Some of them stood out to us, whether that’s, hey, most developers are—80 percent of the developers are coding as a hobby. 

And there's a diversity element there. Like how do we make sure that even newbies or people that are new to programming feel included as part of this? Or the fact that you have people that are less than 17 years old, 18 years old, we're talking about at least 50 percent of the people that we polled were, globally, less than 18 years old. So, we’re talking about an age demographic inclusion metric that's very important to say how do we welcome youngsters into the flow of making sure that they are participating? 

Or even more specifically around gender diversity. And if you look at that there's, it's heavily lopsided in terms of males and females. And we say, I think approximately in only 11 percent of our US survey respondents were women this year, it was a slight improvement from last year, about 9 percent last year, but still very, very small. And if you think about that, it's not representative of the world's developers. I grew up in India, and just within that country alone, the number of women developers that are emerging into the workforce, this is a fascinating number. And obviously, I moved here for college and joined you in Maine when I was 17, but the point is, it’s just an important statement and, kind of, a piece of work that we need to make sure that we are representing what's truly in the world. 

And so, we are very committed to making sure that diversity and inclusion is a top priority for us. This starts, by the way at our own company. Like the people that we hire, my own leadership team. So, we’re making a very conscious effort to make sure that we are very much reflecting our community in a way that is fully representative of the true user-bases out there, to make sure we lead by example. And you will see us do many things this year to make sure that we made progress on this key initiative that will keep you posted on.

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Corey: How do you wind up effectively balancing between two very important but almost inherently oppositional goals. One, to wind up continuing to drive change within the community and make the product offering and discourse, frankly, better, versus the other side of avoiding the Digg or what seems to increasingly be the Reddit trap where a redesign drives the community members away, or—anytime you start changing a community, there's a large group of people out there, and often I'm one of them who despises change, or anything that smells of change because we delude ourselves into thinking that the world will hold still long enough.

Prashanth: Yeah, phenomenal question. I think that a couple things to note here. I think one is, we are very much convinced that it is important for us to make sure that we seek input from a very broad set of folks, just like our developer survey that I mentioned. We've got new mechanisms in place, like The Loop survey, which we've launched, which really expands the number of voices that we have in terms of the voice of the community, so to speak, so we really understand what people want, to make their experience even better. And so, that change or set of changes—because historically we have completely relied on just mechanisms and forums like Meta, which is home to our tremendous power user base and the folks that—such highly valued members of our community. 

But it does represent a very specific portion of our community and doesn't necessarily include the entire population that we want to really hear from. So, that is important. We want to make sure that we are making sure that we make changes to the question asking process, Questions Asking Wizard, Unfriendly Robot, and others. And this is really led to some really strong results. So, more people are asking questions without seeing a dip in the question quality. And we cut the number of negative comments nearly in half without seeing any sort of reduction in the overall comments. And ultimately December was our best month ever in the history of our company in terms of new signups. So, there are things that we are doing that are resulting in, I would say, positive traction.

 Now, to your point, not everything is easy to be managed and terms of change. So, we have to articulate—we need to do a much better job, by the way, as a company—of articulating how and why we're including these new mechanisms, what is the role of existing mechanisms like Meta? Because they're obviously very valuable for us, as we continue to evolve the community. How do we make sure that our power users are part of the journey of helping us get to the overall goal of making this community even more impactful? Because clearly they care about that. So, there's a lot we’re going to manage around that. But I think that we are very committed to making sure that we have a robust listening process, to make sure we listen to our community, and also to have bi-directional feedback. And to make sure that folks like me and others are going to be very active, to make sure that the community is always in the room and we have a key conversation. We're going to make that happen.

Corey: One thing that—I don't know if it was a problem or a change that I was somehow tripping over based upon asking stupid questions, but it seemed for a while that every third time that I googled for a particular error message, the top result was always something on Stack Overflow. And that was always a conversation that was closed as off-topic or marked as a duplicate, yet somehow it was always at the top of Google search results to the point where it became a recurring joke. I don't see that happen nearly as much anymore, to the point where when I do it feels like it's almost an oddity in its own right. Is that something that was a change on your end? Was that just I learned to Google for better questions? Or was there a flare-up in that that suddenly just wound up getting fixed, but everyone thought that was how it was supposed to be?

Prashanth: Yeah, this is interesting. This is about basically improving our code of conduct and educating our moderators and power users. So, it's making sure that we are very specific about how we improve on a day to day basis. We make sure that people are evolving how they actually operate in the community and how we bring along the community for that ride. So, that's effectively what you're seeing there. And to make sure that our moderators are enabled with the right sort of information, and they are really trying harder to make sure we help new users and beginners, and not to be too zealous about our gatekeeping so that people are more welcoming here internally.

Corey: It definitely seems to have had a meaningful impact. Now, I have to assume that there's more to your company, as far as revenue models, as far as what you folks do, than providing the answer to me frantically googling while on a phone screen, “How do i FizzBuzz?” What are you folks beyond the community, which is the way most of us tend to interact with you?

Prashanth: Yeah, thanks, Corey, for that question. I think that Stack Overflow is mostly known for the community that we have established over the past decade. So, the 50 million folks that show up to our website every month. There's the additional 70 million that to our Stack Exchange websites, and then 150,000 people that sign up every month for new accounts. But what's not well understood and perhaps not as recognized is the fact that we are a true company, a SAAS company. And so, very much like how GitHub had its own enterprise journey, we've been on that journey for a few years, it's a couple years. And that's one of the reasons why I'm also on board, which is to make sure that we really build a sustainable and long term and successful business at Stack Overflow in addition to, obviously, the core mission of making sure that we really help our developers and our technical workers. So, in terms of the products, we have our Talent business, which is really—we have something like 40,000 jobs were posted on Stack Overflow for jobs in 2019. Just matching against close to a million searchable profiles of developers who are interested in being contacted by job on Stack Overflow Talents. So, that's our first business, the talent business, it's a big area. 

And we have a second business which is called the advertising business, which is something like a million developers found new and useful tools, after seeing a company advertise on one of our sites this past year. So, think about Microsoft advertising about Microsoft Azure, or Google advertising about BigQuery, those sort of examples. And then, our third product is our true SAAS product called Stack Overflow for Teams, which really allows developers and product folks, etcetera, to really collaborate and ship products really fast within their organizations. And so, we've had hundreds and thousands of engineers who have leveraged our product in 2019. As an example, Microsoft has something like 70,000 developers on Stack Overflow for Teams. 

So, those products are just the beginning of, I would say, our commercial journey, and some of those products, especially the Stack Overflow for Teams, is growing at a very rapid rate. And we have all the fortune 100 companies, really some phenomenal logos like Bloomberg, and Microsoft and a whole bunch of other fast-growing startups like Expensify, etcetera, that are all leveraging Stack Overflow for Teams, and are just amazing use cases internally in these companies. So, we're really tagged against the future of work, if you will. So, we integrate with Slack and Microsoft Teams, and very soon with GitHub Enterprise and JIRA, to make sure that we're really part of the developer workflow so that we help developers are faster and faster as they ship products.

Corey: As you take a look across the larger ecosystem and community, what do you think is the most misunderstood about the company in the common case?

Prashanth: Yeah, it's a great question. I would say, it's probably the notion that Stack Overflow is a community, and it's really not—people don't truly understand that—so the other products that we have that are also tremendously valuable. I think most people just know us about the community and assume that we don't have a revenue model, when in reality, we have a very robust revenue model that's, in many ways, just about to really explode in a good way. So, that's just, I would say, the biggest, I would say, lack of understanding. And I think the other part is, I think people just don't realize the scale at which we operate. I think people just don't understand that we are pretty much, I would say, the life-force of the internet. I mean, everybody—[laughs] there is not a single developer in the world that does not use Stack Overflow. I mean, that is not a kind of, a brash claim. I think that it's hard to come across a developer that has not used our website, one way or the other. It is the new way, or if you will—

Corey: Well, many of us may not admit it, but absolutely we use it.

Prashanth: Exactly. And so, I think that is, I would say, it's the unsaid, kind of, statements and most people—I don't know if everybody realizes that, realistically.

Corey: Yeah, well, what would you do if you had this problem in an interview? Well, I'd google it. Well, what if Google is down? That's okay. I already know Stack Overflow’s address. We're good. It becomes one of those fun exploratory things. I guess, what are you seeing or concerned about as a CEO who is not a founder of the company, effectively their first external CEO, what's top of mind as you step into what are admittedly some very big shoes.

Prashanth: Yeah, so I've had—a lot of what I've done so far as to really listen to all our employees, our community members, and our customers, of our products, and constantly, every week, I’m talking to a large number of them on a regular basis, just to really make sure that I have the full context to really make the right decisions in terms of the types of products that we build, what we need to evolve as a company, etcetera. So, a lot of work where I think what we're trying to accomplish, I think, even in my first 90 days of the company, one of my observations is that I think a lot of, while the external community and the tech industry has very rapidly evolved if you think about the cloud, and you know this better than anybody, which is between Amazon Web Services, and Microsoft Azure, and Google Cloud, and concepts like Kubernetes, container orchestration, Lambda with Serverless. 

There's just a whole world where infrastructure and DevOps and software engineering, software frameworks, all of those things are, sort of, very much colliding, and really the lines are blurring. And so, even for, sort of, our experience on the community or our community websites, I don't think have evolved as much as, the end customer, the end community member has evolved in terms of what they do on a daily basis. So, there's a lot of what we have to improve in terms of the experience between our Stack Exchange websites and our Stack Overflow website, and to make sure that people have all the things at their disposal, whether that's DevOps concepts or cloud concepts or Stack Overflow concepts, all questions and answers at their fingertips. 

As an example, we have 182,000 questions on Azure. And we have 87,000 questions on AWS and 20,000 questions on Google. But it's actually not well understood or well recognized because it's actually sitting in Stack Exchange, sort of in a corner with a bunch of other websites that we had. Their phenomenal properties, but it's away from Stack Overflow. And most people do go to Stack Overflow. And we also have, by the way, communities like Information Security, and DevOps, and Data Science, and so on. So, there's a lot that we can do to make sure that we bring those to the forefront, so people actually are able to leverage all these great resources. So, that's really, I would say, a lot of what we're thinking about. Make sure—one of the things that I've noticed that we have not necessarily evolved, just like the external developer [unintelligible] outside our company, has evolved very rapidly, and we need to do a much better job of doing the same on our end.

Corey: Fantastic. Last question before you go, and I just wanted to get your take on this. A while back, Joel had a blog post—I think it was a blog post, it could have been a bunch of other different media, I follow basically everything he says sooner or later—and what struck me was the way that you folks focus on employee experience, it's sounded, hands down, like one of the best companies in the world to work at. And this is going to sound petty or like I'm being sarcastic, but I swear I am not. The fact that every engineer there gets the option of having their own private office is mind-boggling to me. I have worked in too many startups where you're sitting cheek to jowl with everyone next to you that holds still long enough. And just the idea of a private office is hands-down one of the best opportunities to differentiate yourselves. I don't know why other people don't do it, but it is one of the most aspirational aspects of Stack Overflow culture that I think I’ve ever heard of.

Prashanth: Yeah, no, absolutely. I obviously can't take credit for that. That's all Joel and his philosophy and his—which I totally agree with, by the way, which is really making sure that we provide an environment for our engineers and our developers to make sure they're highly productive, in the same vein of what I've discussed about various products, etcetera. But it's the physical environment, how do you make sure that they actually have the space for them to be, sort of, in the zone, so to speak, to be able to really contribute at their highest level? And so, I think it's very distinctive about our culture. One of many things, by the way, that makes Stack Overflow such a great place to work for. And so, we welcome—we're always hiring, by the way, so if anybody's listening here, we are always looking for new and talented Stackers as we call them, so please reach out to us.

Corey: Thank you so much for taking the time to speak with me today. I really do appreciate it.

Prashanth: Same here, Corey a real pleasure, and great to reconnect with a fellow Black Bear.

Corey: Yes, eventually, those scars will one day fade as soon as the Maine chill gets burned from my bones. Prashanth Chandrasekar, CEO of Stack Overflow. I'm Corey Quinn, and this is Screaming in the Cloud. If you've enjoyed this podcast, please leave a five-star review on Apple Podcasts. If you've hated this podcast, please leave a five-star review on Apple Podcasts and tell me exactly what my problem is.

Announcer: This has been this week’s episode of Screaming in the Cloud. You can also find more Corey at ScreamingintheCloud.com, or wherever fine snark is sold.

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