Stack Overflow

If “no surprise medical bills, ever” sounds like a dream perk, Stack Overflow might be your next favorite place to work.

In this episode, Jena chats with Stack Overflow’s Chief People & Culture Officer, Debbie Shotwell, about building an inclusive, mission-driven, fully remote culture where experimentation is encouraged and growth is real. They dig into how a beloved public Q&A platform for developers evolved into a global business with enterprise products, ads, and AI partnerships, plus how Stack Overflow navigates change with radical transparency.

What you’ll learn:

• Stack Overflow’s public Q&A platform for developers, Stack Exchange network, enterprise tools, ads, and AI data deals with Microsoft, Google, AWS.
• From 2008 garage startup to $200M business serving devs in 118 countries.
• Fully remote for 320 Stackers across engineering, product, sales, marketing, and people teams.
• Welcoming culture with buddies, ERGs, flexibility, and safe experimentation (no one’s an expert in AI).
• Internal mobility via marketplace, Stack Overflow Academy, and 12-18% promotion rates.
• Transparent leadership post-restructuring, with growth and selective hiring ahead.

Stack Overflow highlights:

Founded: 2008

Team size: 320 employees worldwide

Ownership: Acquired by Prosus in 2021; operates independently

Work model: Fully remote, global team

Culture: Mission-driven, welcoming, flexible, inclusive, experimental, transparent

Unique Perks & programs:

• 100% company-paid health benefits (medical, dental, vision) + HRA covering all deductibles
• 16 weeks paid parental leave for all; 4-week sabbaticals after 5/9 years
• Monthly Learn, Share, Grow Days + $2,500 annual development budget
• Nine ERGs, monthly AMAs, inclusion/engagement surveys with action
• Internal “marketplace” for cross-team projects and boomerang opportunities

To learn more about The Stack Overflow:

• Careers Page (They're hiring!)
• Linkedin Page
• Debbie's Profile

Transcript

Jena Dunay: Hello friends, and welcome back to another episode of Culture Uncovered, where we go behind the scenes of the coolest companies to work for of different ages, stages, industries, you name it, we have seen them all. And so we are super excited today to welcome Debbie Shotwell, who is the Chief People Officer and Culture Officer of Stack Overflow. So Debbie, thank you so much for joining us.

Debbie Shotwell: Thank you, Jena, for having me. I'm so excited to talk to you.

Jena Dunay: I'm excited to have you on this call and learn a little bit about you and have our listeners learn a little bit about Stack Overflow. It's so fun for me, as I mentioned in the intro, to learn from different people who have been part of different organizations, and about those different organizations depending on their industry. We've had so many different types of industries on this show, and I'm excited to welcome you and learn a little bit more about what you do. So let's start there. What does Stack Overflow do?

Debbie Shotwell: Well, Stack Overflow is a unique company, and we've gone through lots of changes over the years. But the most exciting part is that we're a public platform for developers. And what does that really include? It means that developers go online and actually ask questions, and it's a public platform. It's community‑driven, so it's mission‑driven, and programmers ask questions about practical coding, receive answers from their peers and experts, and the content is peer‑reviewed and curated by the community through a voting and reputation system. So people earn points for responding, and they actually earn points for asking questions, which helps ensure the quality and the relevance. It's a very well‑known platform for developers. It's been around since 2008. The resource becomes a primary go‑to resource for developers worldwide, and we're in 118 different countries. It's amazing. And every day, programmers are learning and solving problems together. So that's one part of the public platform.

But we also have a Stack Exchange network. That Stack Exchange network is our flagship and people network, and they do Q&A in diverse subjects. For example, there's a cooking Stack Exchange, a Biology Stack Exchange, and a Math Stack Exchange. These have been around as well, and people host and ask questions and share recipes on the cooking exchange. It's quite interesting.

The other part of our product is Stack Internal. So the company offers a private, secure version of its Q&A platform for organizations to use internally. The service allows companies to centralize and share proprietary knowledge among its teams to improve efficiency, streamline, and internal collaboration. The best part about this is during COVID, when everybody had to go home, our Stack Internal, called Teams at the time, became a big hit with companies because everyone was remote during COVID.

And there's one more component. I know I have so much to talk about on Stack. There's advertising and data licensing. So Stack Overflow provides advertising services, Stack Ads, for brands to reach large communities of tech professionals. It also licenses vast amounts of technical data to third parties, including training AI tools. So for example, this past year we've done business with Microsoft, ChatGPT, Google, AWS. That just gives you a little bit of an overview of what we're doing.

Jena Dunay: Wow. Just a couple of casual companies. So it sounds like a lot of it predominantly started as a knowledge‑sharing platform, really, and has grown into something community‑led and then been able to develop other revenue streams based off of that community essentially, is what it sounds like to me. Okay, so it started, I think you said 2008?

Debbie Shotwell: Yes. That's exactly right. 2008 is when we started. I know, can you imagine? It was September of 2008, worst economic time. But remember, it was mission‑driven. It was started by two gentlemen who started it basically in their garage. And it was a way for developers to work together, provide services, and exchange information, and it was very well known right away too. It was a hit.

Jena Dunay: Right, it was a hit. It was a hit. Okay, so how many people now work at Stack Overflow? As an employer, tell us a little bit about that.

Debbie Shotwell: Yeah, so we have about 320 employees that work for the company full‑time all over the world. So we're a very diverse group of Stackers, as we call ourselves. And we're about a 200‑million‑dollar company. We're owned by Prosus. They bought us in 2021, 100%, but we run and operate separately. Prosus is a company out of Amsterdam.

Jena Dunay: Okay. Interesting. So about a 320‑person company, 200 million dollars, owned by another organization, but really living independent of that. Okay, so are most of the people you said fully remote, correct?

Debbie Shotwell: We're fully remote. We used to be in New York City and London; we had two offices. After COVID, we said everybody can go back to work. Not very many people were taking that opportunity. So in 2023 we shut down those offices, and we're 100% remote.

Jena Dunay: Okay, I have so many questions about that. Tell me, when I'm thinking about a company like Stack Overflow, my brain immediately goes to “it's only developers who work there.” But that's obviously not true because you and I are talking, Debbie. So tell us a little bit about the different departments. That helps people understand what you all do beyond maybe just the development side of things.

Debbie Shotwell: Yeah, that's a great question. So we do have a fair amount of engineers in the company. Yes, a majority of them are engineers but we also have product people who develop our product and work on the design of the product. We also have a marketing department that helps market our products, remember products, because we have many products. So it's not a simple one‑product shop, and we have different products and we have to market them very differently.

We also have a fairly robust sales team that actually works on the ads, internal offerings, and data licensing. We have sales, we have a finance and accounting department as part of general G&A. We have a legal team. We have a people team, my team is called the People Team. And we have subdivisions within engineering. You have your developers, your software developers, and you also have people that work on AI development, and those teams are built out to support our general community.

So, for example, we have a community team. We have people that really focus on our community and monitor our community. Those monitors are actually not even employees, they're volunteers that work and monitor the community. So if someone's asking inappropriate questions or there's escalation areas, we do have moderators that are volunteers, which is even more amazing. And a lot of times our moderators become our community managers. So we have a fairly robust team all across the world. We have people in the UK, Brazil, Spain. It's nice to talk to people from all over the world.

Jena Dunay: Yeah, very cool. Now, how, Debbie, did you come across Stack Overflow? Have you been in the tech industry for a long time? Walk us through that.

Debbie Shotwell: Yeah, so I have been in the tech industry for a long time. Let's say 20‑plus years. When I left my previous company during an acquisition, I was talking to a recruiter and I said, “I'm gonna take some time off. I'm gonna enjoy myself.” And she kept calling me, and she said, “Oh, I've got something. I have this opportunity.” I'm like, “I don't think that's right for me.” When she called me again, she said, “I have a new one. It's with Stack Overflow. There's a new CEO of Stack Overflow, and he's looking for someone to come in and help him.”

I've actually worked with four new CEOs now in my career, which is great. I really like it because they're new at their job and they don't necessarily know everything; they have a high energy. So I met with Prashanth, and I knew Stack Overflow. I knew it because when I worked with BigCommerce, I used the advertising feature to post jobs on the talent side. So I used Stack Overflow. I had some connection. I didn't know very much about the community side, the developer side but I met Prashanth, I met the team, and I just really liked what they were doing and what they were looking for.

I was a good fit because I came from the HCM space. So I know a lot about HR and a lot about technology because I've worked for PeopleSoft, I've worked for Taleo, I've worked for Saba Software. I've worked for these big tech companies, but all very HCM‑focused. So I could come in and I knew the tech side, but I was learning something new, which was really ideal. I joined in 2021, so it'll be five years in January.

Jena Dunay: Wow, congrats. What keeps you there?

Debbie Shotwell: Definitely the people and the culture.

Jena Dunay: Yeah, how would you describe the culture?

Debbie Shotwell: Well, the culture is very unique in that we have a place where people feel included, welcomed, flexible, and encouraged. Because we're a very mission‑driven company, it leads to a company that's willing to experiment and make mistakes. It's okay to make mistakes and try new things. Our whole AI strategy is, we're trying new things on the fly. And it's great. Nobody's an expert. We don't really know what we're doing, so we're trying new things. It's a great place for people who are energetic, want to learn, and are willing to say, “Hey, I don't know it all,” and you have to be willing to roll up your sleeves.

Jena Dunay: Yeah, no one's an expert. Okay, I love that. What are some other examples, you had mentioned an encouraging environment. I love these phrases, but we often hear companies say that and we don't really know what that means. Some of those words that you used, how do they tangibly play out in the day‑to‑day life at Stack Overflow for Stackers?

Debbie Shotwell: Yeah, and these are words that my employees have told me. So this is great, this is their language. “Welcoming” means that when somebody starts, they feel embraced. They have a buddy, and then they receive extra buddies from different departments. So there's always someone there to help you. People are willing to give you time, give you space.

When we talk about flexibility, we talk about someone really feeling like if they call in and say, “Hey, I'm not feeling well today,” it's not like anyone gets mad or angry. They realize people have lives outside of work. Going on vacation, we have a very flexible PTO policy, considered unlimited. I don't think our people take advantage of it because they care about getting the work done, which goes along with being mission‑driven company.

I really do believe that people feel like they're welcomed, that we're flexible. And this inclusion piece, we have a very diverse group. I talked about this. We have nine ERGs for a really small company, and people bring their true selves to work. They can be who they are and they can talk about diversity with their fellow ERG members or just openly as a company. We encourage people to be themselves and not to be afraid to say what's on their mind. And no one feels like they're attacked when they make a mistake. I talked about that a little bit earlier.

Jena Dunay: Yeah, which is a really common piece in especially high‑stakes environments. I started my career off on Wall Street, and I literally got yelled at for making mistakes. That's literally what happened to me.

Debbie Shotwell: Yeah. I've been yelled at too, sworn at, people told me terrible things during my career. But you don't see that at Stack Overflow. It's a very, very unique culture.

Jena Dunay: Yeah. Tell me, you mentioned “obviously unique.” One of the things that I love to ask chief people officers or guests that I have on the show is: what are some unique benefits that you have, or perks, or interesting pieces that are unique to your organization, that Stackers get to take advantage of if they're a part of the organization? For people that are listening to say, “That's interesting, I am now intrigued by this company because of...” It's kind of like the hook, if you will. What's the hook?

Debbie Shotwell: Yeah. So our hook, and it's always been the hook, and I'll give our founders all the credit. The hook has been we pay for all of the employee benefits 100%. So people say, “Wow, that's very unique. Is it really true?” Yes, we have a fully‑paid benefits plan that includes medical, dental, vision. We also have an HRA that actually covers all your extras. So if you had a deductible as part of your plan, the HRA just comes in and swoops in and pays it. That is very unique. It's an HRA, it's a health reimbursement account, which you've probably heard of an HSA; it's an after‑tax account. This is an HRA, so it's a little different. The company gives you similar to what you have in an HAS, 10,000 dollars for you and your partner, or 12,000 dollars for a family. And that money covers all your deductibles or any extras that aren't covered under the regular plan. They just come in and pay it. You don't have to do anything. They actually just come in and pay it, which is great.

Jena Dunay: Yeah, that's amazing. Do you know why that was one of the things that they prioritized from the very beginning?

Debbie Shotwell: Yes, and I know why we keep it too, we're very clear on that. Number one, the founders didn't want their employees to worry about any medical expenses. They didn't want them to worry if they got sick or if there was something wrong. They didn't want them to have big expenses. So that's the reason. We've kept it because it's tradition. Like you said, and you're right, it's the hook. It keeps people. It's a great retention tool, and it enables us to hire people. When they hear it, people don't believe it. They ask over and over again, “Send me the documents; we want to hear more.” They really like it.

But we also have other things that keep people here. We have enhanced mat and pat leaves for employees. We have sabbaticals. For parental leave, it's 16 weeks for both; we're equal. We offer sabbaticals after five years and nine years, so four weeks after five years and then another four weeks after nine years.

Jena Dunay: I love a good sabbatical. Are you about to enter into your sabbatical year maybe, Debbie? You're hitting your five‑year mark. Are you already planning it?

Debbie Shotwell: Yes, I am. It's great. We have a lot of people who are hitting their sabbaticals. So we've had to put together an enhanced plan to help managers and leaders manage this, because we're going to have like 70 people have sabbatical next year. It's unbelievable. It's a lot.

Jena Dunay: My gosh, that's incredible and also probably stressful to some degree from a company perspective. But it's very exciting, and it's an awesome perk for sure.

Debbie Shotwell: And we also have LSG days. So once a month on Fridays, we offer an individual LSG day. LSG is Learn, Share, Grow Day, so you can spend time learning. We have a department one on the alternate month and a company‑wide one. We do things like the product roadmap, our product team will come and talk about the product roadmap. Or we'll bring in an outside speaker to talk company‑wide.

And then we have an employee development budget every year. Every employee gets 2,500 dollars for a budget. We have employee resource groups, an inclusion survey three times a year, and an annual engagement survey, which we action and we measure all our results. And then we have employee and manager AMAs monthly, and we have an SLT update monthly. We have hosted manager meetings that are pretty casual, but people can come and ask any question they want, similar to our employee AMAs. So we actually do have quite a few benefits working here.

Jena Dunay: Yeah, the AMAs are very interesting. I also like how you use that phrase of AMA, it's very 21st‑century of you, I love that. Instead of calling them town halls, an AMA is great. These are super cool. I'm going to be writing all of these down and including these in show notes if you're somebody who's listening and like, “We need to go back and listen to whatever she just said,” because there are a lot of really cool perks and benefits that you all offer.

You had mentioned the professional development budget, which I think is a great asset to your organization. It's one of the things that I get asked about a lot: “I need to be able to be at a place where I can grow.” And growth means a lot of different things to a lot of different people. Being able to learn is one of those things. But another area is around: are there opportunities for me to get promoted? What does that look like? What's your perspective on career pathing as it relates to culture and the people within your organization?

Debbie Shotwell: Yeah, so we have something called our Stack Overflow Academy. Every position, every person, can fill out an assessment and say, “Here's where I am today, and this is what I want to learn or what position I'd like to go into.” That curates content for an individual so they can use it on their individual Learn, Share, Grow days or anytime. As they learn, it keeps it in the library so we can see what employees are doing and learning.

Every year we offer opportunities for promotion. So if you come in as a junior developer and you want to be a Developer I or II, we have a very clear path for someone in their career. Ultimately, every year we look at our overall stats on promotions. The average promotion rate at most companies is between 8 and 10%. We've been averaging anywhere from 12 to 18% a year. So we're promoting people more than the average.

Jena Dunay: Yeah, that's awesome. I think it's helpful for people to understand what makes Stack Overflow a really great place to work and why people stay there. Even your stat around people being there for five years and there being 70 people taking a sabbatical next year, that shows a lot out of a 320‑person company. That shows a lot from a retention standpoint. So that's really impressive, Debbie, for you and the team, and congrats on that.

Now, we talked about all the wonderful things about Stack Overflow, but no company is perfect. So give us a little bit of an idea of what are some areas that you feel like the organization needs to work on, or where the culture is imperfect, if you will.

Debbie Shotwell: Yeah, I think there's been a lot of change since 2021, I will be honest. We had about 620 employees in late 2023, so we went through a massive organizational shift and change. We were purchased, they said “grow, grow, grow,” and then, like many companies coming out of the COVID era, it became “we want you to be profitable.” So what does that take? We had to shift our organization. We had to shift our departments. We reduced hiring. We made changes.

So obviously, two years later, we're in a much better place than we were. However, our workforce is very different now than it was before. And there are still some cultural residuals from doing organizational changes and cuts. That's the area where we're trying to build confidence with people and say, “Hey, there's always going to be change. We are going to see our jobs change, and we're going to see the market change.” The job market right now, as we all know, is not great. And that's the reason why we have so many people that are staying. You could say job‑hugging, but you have a lot of people that are staying right now because they don't want to go somewhere else and risk going somewhere where they're the last person in and the first person out. So we continue to listen to our people through engagement surveys, inclusion surveys. We ask questions.

That's the reason why we have those learning opportunities and open forums where people can ask very honest questions. They want to know where we're making money. If we're not making money, we share all that data. Our CFO is really open and transparent with our employees. I think that's helping. It's building confidence. When we're not doing well, we're also very honest and we try to make shifts in our org, but we are very upfront about it.

So if someone comes to me and they ask the question, “Are we going to have a layoff?” I've always told my leaders this: don't say no. You need to be honest and transparent. The organization is shifting and ebbing and flowing at all times. There could be organizational changes, not necessarily a layoff, but where the org is going to shift and maybe somebody is doing something today that next year they won't be doing, but they could still be with the organization. That's why we push development with our people and the Learn, Share, Grow day opportunities. We have something called the marketplace where they can go find opportunities within the org that we post that say, “Hey, you can come and work in my department just a couple hours a week,” or whatever it is, and learn something new.

We actually have a recruiter, this is a great story. He's worked for the organization twice, so he was a boomerang. He was the recruiter, and he loves Stack Overflow so much he wanted an opportunity to learn more about the product area. So he went in and helped them with AI product development. Now he's doing an apprenticeship with the product team and he's loving it because he's just learning, and maybe someday he'll go work in our product team. I think it's amazing. You don't always see those opportunities in companies.

Jena Dunay: You know, it's so funny you say that. I had one other company that I interviewed this past year that talked about having an internal marketplace, and that has been my favorite idea that I have heard out of all the cool benefits. We've had some cool perks, that is my favorite idea by far. Because it is true learning and development. It's not “here's a course, good luck.” It's like, “Here's an opportunity to have a seat at the table; join us.” And that's how people learn and grow and move laterally within an organization.

Also, Debbie, I just want to applaud you. I have done this podcast now for over a year, and we've had companies on here that have had to go through RIFs or layoffs. We actually help companies when they're going through outplacement; we provide outplacement services. And we have never had anyone be honest about, “This was terrible. This was not fun. We went through it and we're on the other side, but there's been some residuals from that.” I just applaud that transparency because that is not normal for organizations, and it's hard to do because it feels scary but it's a reality. I just want to thank you for sharing that, because that's not easy to do and being honest about it.

This has been super fun to get to know you more. Tell us a little bit about what the next 12 to 18 months looks like for Stack Overflow. Are you guys going to be hiring? What might that look like? Obviously you talked a little bit about there's always transitions within workforces. Just for those folks that are listening that are like, “Wow, this is a really cool organization. I really like Debbie. She's a straight shooter. I like what this organization is about, and I love some of the benefits that they have and the people that seem to be a part of it.” Where can they learn more, and are you guys going to be hiring?

Debbie Shotwell: We're always hiring. I always say there are always some jobs open because people do leave organizations. So we're always looking for great engineers. If they have AI experience, it would be a plus right now. That is the number‑one skill everyone's looking for. But we also look for other jobs in other areas, we talked about it, sales, so account management sales, direct salespeople, and also people that have worked in ad sales. We look for ad salespeople. We also look for people that have a finance and accounting background. We have a great marketing team, and we're always looking for great people.

We don't have a lot of opportunities now, but I see growth coming next year and the year after. I always say, if you're really interested in a job, try to find a connection in the company, somebody that works there who can tell you more about the company, somebody who can refer you. We have an excellent employee referral program up to 5,000 dollars. Somebody can earn if they refer someone and they get hired. It's an amazing thing for Stackers to receive that referral bonus.

So if you're interested, look for a connection or someone that might know someone else. I always recommend this to people. Sometimes the key is: find the leader in the organization and send your resume and cover letter directly to the leader and say, “I'm so interested in Stack, and here are the reasons why. This is what I could do for you.”

Jena Dunay: Yeah, “this is what I can do for you” is the key there. So many people stop and say, “Hey, I'm so excited about this role. Here's my resume.” And then what that requires the other person to do is a lot of work. You need to close the loop for them. If you're a listener of this and you're a job seeker, close the loop for them. Make it easy for them to bring you into an interview. They want to interview good people. They want to interview people that bring value to the table. They don't want to go through all the zillions of resumes. They want to find somebody that's going to be a good fit for their team. A little bit of gumption, a little bit of clarity, and a little bit of “what value I can bring to the table” is always going to be more beneficial to a hiring manager. So I love that you said that, Debbie. Where can people go to find out more about your organization?

Debbie Shotwell: StackOverflow.com/careers. We have a whole page, and it tells you all about the benefits I just talked about, and it tells you all the cool stuff about Stack Overflow.

Jena Dunay: Awesome, Debbie. Thank you so much for joining us today and sharing a little bit more about Stack Overflow. I'm super excited for your growth in the coming years and excited to see what your organization does. So thank you.

Debbie Shotwell: Thank you, Jena.