The Stack Overflow Podcast

A conversation with Stack Overflow's new CTO, Jody Bailey

Episode Summary

On today’s episode we chat with Jody Bailey, Stack Overflow’s new Chief Technology Officer. He recounts his path from physics to sales to programming and shares thoughts on what our organization can build for the future.

Episode Notes

Episode notes

Before joining Stack, Jody spent time at Pluralsight and AWS Training, two roles that helped him to understand the growing market for online educational self-taught developers. We interviewed his former colleagues at AWS training in this episode.

Enjoy the frustration of debugging your own code. Maybe you it brings you eustress? Ben does not experience this, nor does he like the classic video game Myst. But it takes all kinds.

Interested in learning more about the changing trends in Developer education? Check out data from our latest Dev Survey and research from the teams at Skillsoft, another member of the Prosus Ed-tech portfolio.

Today’s lifeboat badge goes to Anton VBR for explaining: What's the function of dedent() in Python?

Episode Transcription

Ryan Donovan Through no fault of my own I ended up reporting to the CTO. And one of the things I realized by working with the CTO directly is they had what I call the executive laser beam, where they would point it somewhere and people would move. So where do you want to point your executive laser beam at Stack?

Jody Bailey Oh, that's funny. I used to refer to it as like the CEO lighthouse where it would kind of circle around and every once in a while it'd focus on somebody. So yeah, I think we're on the same page there.

[intro music plays]

Ben Popper Gatsby is the fastest frontend for the headless web. If your goal is building highly-performant, content-rich websites, you need to build with Gatsby. Go to to launch your first Gatsby site in minutes and experience the speed. That’s Head on over. Use that link. Let them know we sent you and help out the show. 

BP Hello, everybody. Welcome back to the Stack Overflow Podcast, a place to talk all things software and technology. I am Ben Popper, Director of Content here, joined as I often am by my colleague and collaborator Ryan Donovan. Hey, Ryan. 

RD Hey, Ben. 

BP We have an exciting episode today. We're going to meet Stack Overflow's new Chief Technology Officer. I got to meet him at our company meetup, the first one we'd had in two years since the pandemic started. It hadn't been officially announced yet, but we're using this podcast and the announcement this week to kick things off so we’re excited for that. So without further ado, we welcome Jody Bailey to the podcast. Hey, Jody.

JB Hey, Ben. How’re you doing? Good to be here. Ryan, nice to see you. 

BP We're doing well, thanks. 

BP I think people from the outside who just visit Stack Overflow casually have a bit of interest in knowing about how our technical staff works and our approach to engineering and everything like that. I guess we could start sort of at the beginning a little bit. Take us back in time. What was it that got you interested in software development and programming in the first place?

JB Great question. I had a very circuitous route to software development and I suspect a lot of the folks you talk to have, especially if they've been at it a while because I think early on a lot of us took different routes to get here. Before I started, I went to school, I studied physics, that was what my degree was in, and I had an interest in electronics and did some assembly type stuff. This will make perfect sense, but coming out of college with a physics degree, I wanted to go into sales.

BP How about momentum and velocity? 

JB Yeah. I thought I could go sell MRI or something about nuclear magnetic resonance, that kind of thing. But it's funny because I didn't have the advanced degree and I didn't have sales experience so I ended up selling restaurant equipment for a while. And then during college I had worked for Fidelity Investments on what was called master console. It was essentially an automated call distribution system to route calls between all the different sites. I eventually went back to work at Fidelity Investments and worked both as a customer support rep and then back at the console where I had the opportunity to do some information system type work. So, kind of the first real programming I did from a work perspective was back then the call switches didn't really tie into scheduling systems and didn't have a lot of reporting. So I took data feeds from our scheduling system and from the call system and then matched people up so that I could say, “Okay, well, they're supposed to be on the phones from this time to that time. How long were they actually on? What's their average talk time, wait time, et cetera? Are people doing what they're supposed to do, when they're supposed to do them, where they're supposed to do it?” Which was very popular with management and a little less popular with the phone reps, as you can imagine. But it was a fast-growing privately held company and Salt Lake City was a relatively new site. It was kind of fun, I actually worked graveyards there during college while I was finishing my degree. I left to sell restaurant equipment and then came back to Fidelity and did the role in Dallas and eventually transferred back up to Salt Lake City. And when I started doing that work I realized that I really enjoyed problem solving with technology and writing code, and I started working on a master's in computer science at the University of Utah. So I was like a lot of people I think, trying to get into a new field, especially programming. I was doing my day job and then doing the programming because I enjoyed it and saw the opportunity, and then was taking classes, and then because I didn't have enough to do, I also signed up to be an administrator at the Linux lab there, and try to stay married. So eventually something had to give and I did not finish the master's degree and I did quit the admin job.

BP Oh, phew. I thought you were going to say you got divorced. You were taking an emotional rollercoaster there. 

JB [laughter] But yeah, so I worked at the Fidelity Systems company where I was a software developer helping write solutions for the people that were working on the phones. So I had kind of the unique perspective of having worked on the phones, understanding the systems, and then being able to write code to replace them. 

RD So you mentioned you liked doing the programming. What did you like about programming?

JB I really like problem solving. And the other thing I like about it, especially in retrospect at this point in time having been a leader or manager much longer than a developer, what I liked was knowing whether it worked or not and being able to make a change and see, “Okay, does it do what it's supposed to do or not do what it's supposed to do and did I impact it?” As a leader, oftentimes you try things and you do things but it's hard to know whether or not it was the right thing or the best thing. And that kind of black and white binary of writing software for me was kind of rewarding.

BP And do you think any of that code is still in production, hanging around, that C++?

JB You know, I think actually there might be. I mean, let me rephrase that. As of seven or eight years ago it still was, which is a little frightening. It's funny because in my career I've moved around a fair amount. Not a crazy amount, but like four years here or there. And I remember checking in with some folks that were working on the product that I was at working on the founding team, and there were people that had been working on it for like 20 years. So it's hard for me to imagine working in the same company, let alone the same product for 20+ years, but there were people that did it and had great careers doing it. 

RD And I think it's increasingly rare these days, but you see them. 

JB Yeah, exactly. 

RD So how did you go from being the guy who writes the code to looking at top leadership positions? What was the path there?

JB Yeah, so the first step was I'd moved into a software development manager position, and looking back, it's almost embarrassing to say how little time I spent as a software developer. I’ll go ahead and come clean, I really only worked as a software developer for little less than three years, and then I moved into a manager position and I had a team of software developers. I did that for a while, and then I actually moved over to a project management role and tried that for a while, all with Fidelity Investments. So I went from Salt Lake City as a software development manager and moved out to New Hampshire and worked as a project manager. And I did that for a while and realized that I really didn't like being that far removed from the technology and the dev teams, and frankly project management's a super hard job. You've got all the responsibility and none of the authority, at least that was my experience. So I left there and I was recruited by somebody I'd worked for before to lead a development team, an organization in Northern Virginia, and then I moved back into the technical leadership there. And then I just kind of stepped from organization to organization, largely being recruited by people I'd worked with before and having the opportunity to take on more responsibility along the way. 

BP One of the things that was interesting to me was your role at Pluralsight if we could dig in a little there. That kind of gets you more into the world of online education, tech education, and the things that you focused on there, AWS and now Stack Overflow. So can you tell us a little bit about how you found yourself at that role and what some of the learnings were there?

JB Yeah. So Pluralsight was a really unique and terrific opportunity. And you're right, I've been kind of working in the technology education space for about eight years now between the two. And Pluralsight, I'd say was really serendipitous. I was really lucky I would say. So I had been working at another organization and decided that I wanted to find a different role, that I wanted to look for a more senior role where I could run the engineering team. And there had been some changes and such so I decided to leave and take some time off and see what I could find. And just going through all the networking, talking with different people at different VCs, people I had worked with, et cetera, I had heard of Pluralsight. In fact, we had used Pluralsight at the company I was working with at the time, and so I was a little familiar with what they were doing, but I didn't really have a good grasp of how much they were doing or how successful they were. It was really interesting to me because at that point, most of my experience with technology training was, you have a trainer that maybe does or doesn't practice but is teaching you what they've learned about the product. And what was unique about Pluralsight was that they had real practitioners creating the training rather than Pluralsight trying to say, “This is what you should learn.” They had people that were actually doing it. And then the way that revenue and everything was managed made it very lucrative for people to provide the training, and it was all online video-based training eventually. They didn't start that way. They originally started doing in-person training and realized quickly that they weren't going to scale and maintain personal lives trying to do that and made that transition to essentially video-based training. And I think that what really set it apart is the authors as they refer to them, the people that are doing the training, that people could really relate to if that makes sense. 

BP Yeah, that makes a lot of sense.

RD Had you been in a CTO role before? And what made you decide to leave whatever that last role is and come here?

JB Yeah. So I was CTO at Pluralsight for a while, and then we kind of changed titles and moved things around, and then I moved to AWS where I was a director. So AWS has a very different kind of leveling system I'd say than a lot of other organizations, and the way that they use titles is pretty different. So the training and certification org was approximately 1,500 people and I reported to another director who just recently got promoted. In fact, you had Maureen on the show not too long ago. I reported to Maureen Lonergan.

BP Yes. That's funny. Yes, we had your former colleagues on, they’ve come up on the show a bunch of times. What are the new on-ramps to being a software developer? Kind of like you mention, what was it that got you interested? And AWS training specifically, but then getting cloud certified and some of the sort of shorter courses you could take for six to eight weeks and then be certified for a job where there's a ton of demand was emerging. Clearly there was a strong signal from a number of people as a great on-ramp that a lot of folks were finding was their inroad to tech if they were coming from a career in a different sector. So I think there was a lot of overlap there, obviously with Stack Overflow, once those people started their courses, inevitably they Google something that's not working and usually end up with us.

JB Exactly. And I think that that's true more and more. I mean, we're seeing not just the certifications, but opportunities. Obviously you've got boot camps, things like that, but I think there's also kind of the intern programs if you will, that aren't strictly for college students. So you have somebody that maybe has experience or a degree in another space, they've done some learning, they've done some training, and there are opportunities within a lot of different organizations where they can come and kind of work for a period of time as an intern with the teams with the opportunity of turning that into full time career positions. I know it's something we did at Pluralsight and there are official programs that AWS does around cloud practitioners and certifications and things like that. But I think the thing that I think is super cool about being in this space is that if you want to learn it, and if you're willing to do the work, there's tons of opportunity. There's such a demand for people that can develop software that if you can demonstrate the ability to do it, there's people that are willing to take a chance and to give you the opportunity to try it. From my perspective, and I know I'm oversimplifying it, but if you're willing to put the time in and figure it out there are so many resources. You have Stack Overflow, Udemy, Pluralsight, YouTube. If there's a problem that you want to solve with software and you're willing to work at it, you can find the resources to figure it out. And then once you're able to do that, you can use that as kind of a portfolio to demonstrate your proficiency and to work your way into a career. I mean, I think largely that's what I did, only I didn't have YouTube and Stack Overflow and all those things. It was back I think before Joel on software even. 

BP Experts Exchange was your only recourse. No, going to Barnes and Noble and getting the most updated paperback. 

JB Yeah, exactly. 

BP Yeah, I know what you're saying. From the perspective of someone who does mostly writing, not coding, I feel like there's both truth and not truth to that. I do think, especially for something like getting cloud certified in a certain platform, the intimidating idea of, “Oh, I'm going to have to be writing novel code and solving complex math problems,” that's not actually the case. You can come in and learn some things through repetition and through road and through logic and be very useful and well-compensated as an administrator. And if you did that for a few years and somebody else came in who was new and had a technical question, it would seem like magic what you knew then about that system and how to sort out errors and things like that. On the other hand, I do think getting back to your earlier thing about what drew you to programming, I'm not the kind of person who enjoys the frustration of debugging something. I really just would rather go write something and get some edits on it or be on a podcast and have a conversation. I think there's a certain engineering mind or a problem solving mind that is comfortable with a level of frustration and complexity which I think can be rewarding long term if you find yourself in this career. 

JB Yeah. Well, I used to always say it, it feels so good after beating your head against the wall when you finally stop. And that was kind of how programming was to me a lot. I was one of those people that just would write stuff and then figure out why it didn't work as opposed to really thinking it through ahead of time. 

BP Totally.

RD Enjoying the sudden absence of pain. 

JB Exactly.

BP I think one of the most clarifying things that I ever learned during the three years here was this word called eustress, it's the opposite of distress, and it's the energizing feeling that you think you're going to be able to solve this problem eventually. People who enjoy that, who like cranking on something, banging their head against the wall knowing they're going to get there, and then two or three days later they get there, and oh, what a great payoff. I'm the total opposite. Did you ever play that video game Myst? I hated Myst. I was just like, “What is the appeal here?” There's a puzzle, there's no answer here. You wander around for days and then it comes to you. I would never do this, but obviously lots of people thought Myst was an all-time classic, so there's a sort of personality that fits the Myst and doesn’t. 

JB And that's programming to you, huh? That's awesome. 

BP Great. So I wanted to get a little bit closer now to your new role. As you looked at the position here and your decision to join Stack Overflow, what were you weighing, what attracted you to this? And maybe from there we can talk a little bit about some of the ambitions you have for this role.

JB Yeah, for sure. So candidly, I was thinking I was going to take some time off and just ride my bike and spend some time in the Pacific Northwest out on the water just to have some fun for a while and just kind of decompress. And when I had the opportunity to talk to Stack Overflow I was really intrigued. I mentioned Joel on software and that was kind of my first intro to Joel and precursor to Stack Overflow and I've been working in the tech education space for a while and so I have kind of this sweet spot I guess, or soft spot, for Stack Overflow in general. And so when I was approached about the opportunity, it was like, “No, not really.” And then it was like, “Well how about if you just talk to the CEO? Talk to Prashanth.” So I talked to him and I was really intrigued. So the things that were important to me when I thought about what my next role would be, was one, I wanted it to be something fulfilling and rewarding, like a lot of us. I also wanted it to be a place that I really enjoyed, where I could work with smart people that were willing to challenge but also friendly. That sounds a little trite I suppose, but I wanted to be a part of a team that really wanted to do the right things for the right reasons, wanted to work hard together, wanted to lift each other up, and I kind of got that feeling from the leadership team. The other thing is I really like working in an engineering-centric type of organization, and obviously AWS is, Pluralsight was, it was founded by developers. And there's different types of technology companies, and AWS is an amazing place and I learned a lot of things and it's very different than working at a smaller company like Stack or Pluralsight where there's a lot more fluidity and a lot more things that haven't already been figured out, if that makes sense, a lot more opportunity to really influence or participate in the evolution of the engineering culture. And those were things that I saw opportunity for here at Stack Overflow, to be part of what I think is a terrific leadership team, to be part of an engineering culture that is really focused on how do we develop great software, how do we solve for our communities, how do we really embrace all things engineering and do it in a way that's super inclusive, which was also a big part of the appeal to Stack Overflow, just how important inclusivity is across the entire organization and particularly engineering. So those things, and that it felt similar to experiences that I've had like at Pluralsight that were really rewarding and a ton of fun, and the opportunity to be on a winning team. I can't lie, being with an organization that's doing really well is fun. When you're meeting your goals, when you're achieving, it's a lot more fun than when things are really hard, and sometimes things are hard for sure, but it seems to me that Stack’s on the right path. There's certainly some challenges and things to overcome and have had to be overcome in the past, but I see Stack Overflow just continuing to get better and providing more value and return on investment for the people that participate and the people that buy it and that's super exciting to me. The whole kind of vision of empowering the world to develop through collective technology knowledge is super interesting.

BP Yeah. 

RD So at my last position, through no fault of my own, I ended up reporting to the CTO. And one of the things I realized by working with the CTO directly is they had what I called the executive laser beam, where they would point it somewhere and people would move. So where do you want to point your executive laser beam at Stack?

JB Oh, that's funny. Yeah, I used to refer to it as like the CEO lighthouse, where it would kind of circle around and every once in a while it'd focus on somebody. So yeah, I think we're on the same page there. I've been here two weeks, I've worked nine days officially I guess, and so obviously I'm still learning and trying to figure out exactly what the most important things are. A couple of things jump out at me, one is hiring. Fortunately for us, and compared to a lot of companies right now, we've got a lot of positions that we need to fill. And I think we've got like 50 different development and IT-type positions that are open, and hiring is always challenging, and I think Stack Overflow has really been on this trajectory in recent years of growing more quickly than it ever has in the past and so I think it's really important for us to work with our talent acquisitions team and figure out how do we continue to hire the best and brightest and how do we do it more effectively and efficiently. So I think that's one area. And then I think the other is as Stack Overflow has transitioned from just a community product to also offering enterprise and business-related solutions, the Teams products for example, I think that technology evolution is super important, how you think about and design a system like Stack Overflow where the most important thing technically is, “Let's make sure we get responses back really quickly. Let's make sure that it shows up at the top of the search list for people,” is kind of a different paradigm than, “How do we develop a feature-rich enterprise solution that still provides all the great things that people have become accustomed to but provides the ease of use, the ease of onboarding, the security, reliability, all those things that go into a SaaS product for businesses and enterprises?” That's a pretty broad and general space to say, but in terms of laser beam, those are kind of the two areas that have jumped out at me in the first nine days, and I reserve the right to change that in a week.

BP We won’t hold you to it.

[music plays]

BP All right, everybody. It's that time of the show. We are going to shout out someone from the community who came on and helped share a little knowledge. We're going to give a shout out to Anton vBR who won a lifeboat badge. “What's the function of dedent() in Python?” All right, thanks Anton for coming on. If you’ve ever had this question, we've got an answer for you. It's been around for about four years and helped almost 20,000 people, so we appreciate it. All right, everybody. Thanks for listening. I am Ben Popper, I'm the Director of Content here at Stack Overflow. You can always find me on Twitter @BenPopper. You can always email us with questions and suggestions, And if you like the show, leave us a rating and a review. It really helps. 

RD I'm Ryan Donovan. I edit the blog here at Stack Overflow. You can find me on Twitter @RThorDonovan. And if you have a great idea for a blog post, please email me at 

JB I'm Jody Bailey, the CTO at Stack Overflow. In terms of online, probably the best place is going to be on LinkedIn. Thanks for having me, it's great to be here. Nice to spend some time with y’all. 

BP Awesome. All right, everybody. Thanks for listening. As Jody said, we're hiring, so check out open positions. Maybe you can hang out with him in the near future. Bye! 

RD Bye!

[outro music plays]