Episode 239: Navigating the AI Shift at Stack Overflow with Jody Bailey
Jody Bailey, the Chief Product and Technology Officer at Stack Overflow, joins Melissa Perri to discuss the integration of AI and product strategy in one of the world’s largest online communities for technologists. Jody shares insights on how Stack Overflow is navigating the rapid technological advancements and adapting to maintain long-term trust within its community.
They delve into the challenges and opportunities AI presents and how it influences product management at Stack Overflow. Curious about how AI is reshaping the product landscape and how Stack Overflow is positioning itself in this new era? Tune in to discover how Jody Bailey is leading the charge at the intersection of technology and community.
You'll hear us talk about:
06:52 - Building Trusted AI Knowledge for Enterprises
Jody Bailey describes Stack Overflow's enterprise solution that maintains a positive feedback environment and identifies subject matter experts. He emphasizes the need for a trusted knowledge layer to manage and distribute proprietary information within organizations.
13:43 - Leveraging Core Strengths in the AI Era
Jody discusses how Stack Overflow is focusing on its core strengths, such as human connection and technical information, to position itself as a vital source for technologists in a world increasingly turning to AI tools for quick answers.
19:52 - Trust, Adoption, and the Limits of AI in Development Work
The conversation covers the importance of trust in Stack Overflow's community and how the platform ensures transparency and reliability, especially when integrating AI into its offerings. Jody highlights the need for a balanced approach to using AI without compromising on human interaction and knowledge.
Episode resources:
Jody on LinkedIn: https://www.linkedin.com/in/jodybailey/
Stack Overflow: https://stackoverflow.com/
Other Resources:
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Episode Transcript:
[00:00:00] Jody Bailey: Developers in my experience are naturally skeptical and certainly. That's true when it comes to AI, right?
[00:00:07] And then you throw in the fact that, there's all this conversation about how their jobs are gonna be replaced by AI and that can create a very uncomfortable culture right? I think about it, even, on a different scale, like when cloud came out, right? Everybody was worried about losing their job and or they were just skeptical that this isn't going to work. And I think that it's a little similar with AI.
[00:00:30] I think many people in many different industries had that, oh, crap moment. And I think you saw a lot of people and businesses, you think SaaS, you think other community sites, had this oh, crap moment. It's oh, we've gotta release something, we've gotta have an AI solution. And you saw this proliferation of AI tools. And, talking with other CTOs, CIOs, et cetera. One of the mistakes I think almost everybody made, which is so fundamental, is we focused on delivering AI solutions. Not solving user problems or customer problems. We were solving for, we have to have AI.
[00:01:08] PreRoll: Creating great products isn't just about product managers and their day to day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you find your way.
[00:01:36] Think like a great product leader. This is the product thinking podcast. Here's your host, Melissa Perri.
[00:01:45] Melissa Perri: Hello and welcome to another episode of the Product Thinking Podcast. Today I'm excited to introduce Jody Bailey, the Chief Product and Technology Officer at Stack Overflow, the world's largest online community for technologists.
[00:01:57] Jody is at the forefront of AI integration and product strategy uniquely positioned to discuss how he's managing rapid technological advancements while nurturing long-term trust within the community. Let's talk to Jody and dive into how Stack Overflow is navigating this new complex space with AI taking the forefront. Welcome to the podcast, Jody.
[00:02:16] Jody Bailey: Thanks, Melissa. I'm excited to be here.
From retirement to Stack Overflow
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[00:02:18] Melissa Perri: Me too. So I am very excited because stack Overflow, I feel is a pretty common thing that if you've worked with developers, you know about it.
[00:02:27] Jody Bailey: Right,
[00:02:27] Melissa Perri: I've been on Stack Overflow to look up questions on how to develop things better when I used a toil with HTML and CSS, which is the bane
[00:02:35] Jody Bailey: right.
[00:02:35] Melissa Perri: of my existence. Um, So
[00:02:38] Jody Bailey: I don't think you're alone.
[00:02:39] Melissa Perri: Yeah, no, definitely not alone. I think nobody really likes CSS, so, happy about that. But how did you end up at Stack Overflow, Jody?
[00:02:49] Jody Bailey: Oh, it's funny actually. 'cause I, I was previous, prior to this, I was at AWS, I was there for a few years and I had actually decided to step down, either retire or take, some time off and just, I don't know, relax or focus on biking or do something different. And I got a call from a recruiter and obviously a lot of us get those calls and you just say, oh, thanks, I'm not interested.
[00:03:15] And they said it's stack overflow. And it's no, I'm not interested. Just talk to the CEO. And I talked to the CEO and had a really good experience, and then I talked to the former CPO and, stack overflow as like you mentioned, as somebody having been in the industry for a while, near and dear to my heart, right?
[00:03:35] And so the idea of being able to participate in, stack overflow and give back to the community. To the technology community having, and prior to that, I was really focused on tech ed spaces. So I was at AWS in the training and certification then Pluralsight before that. And so it just seemed like a natural fit.
[00:03:55] And I came over originally as the chief technology officer. There were a lot of things there that I thought aligned with my experience and things I could do to help. And so it just seemed like an exciting opportunity. And my, my retirement lasted, I think Maybe two months. And I actually, started with the company offsite a few weeks before I, I even started. So that's how I ended up here.
[00:04:20] Melissa Perri: I think Stack Overflow is such an interesting company in these times too because a lot of the community turns to it to ask questions about development. And now with there are large language models and Claude and your chat GPT, a lot of those questions are being answered there. I'm curious what, what does Stack Overflow look like these days, and what makes you really excited about the business there?
[00:04:41] Jody Bailey: Yeah so it's interesting because thinking back to when I joined and thinking about today, a lot's changed, right? With the advent of generative ai, which, a little over three years ago was more of a pipe dream than anything. the job that I have is evolved quite a bit, right?
[00:04:59] You know how people think about Stack Overflow, how they use it, has evolved. It's still, one of the top places developers go to get answers. What we see though, is a lot of the easy answers, the quick things people are able to get those through generative ai. Through the different large language models, through coding agents, et cetera.
[00:05:20] And, they're fast answers, it's easy to get 'em and they don't have to worry about, asking a question in a public forum, it's much more comfortable. It can be intimidating. We've all seen the memes of asking, you know, a question on Stack Overflow.
[00:05:36] So you know, what we've seen is a lot of people are getting those answers there. But they reach a point often where they're just not able to get the answer. They get stuck or they want to understand more about it. And that's where I think Stack Overflow still plays a huge part, right?
[00:05:53] How do we help those people that, that are getting stuck? I was having a conversation with the a senior CTO recently, and we were talking about this and how oftentimes when you're vibe coding or using the agent tools, you get to a point where it's like. You're almost there, maybe you're stuck on something you're not quite sure.
[00:06:15] And I was talking to him, I said, oh, I think Stack's a place, where we can help with that? And he said when I get there, I just reach out to my network and ask somebody. I said yeah, but you've been at this for over 20 years. You have a huge network of people. What do you do if you don't have that network?
[00:06:31] And that's where I think Stack Overflow comes into play. And that's both on the public side as well as within businesses. 'cause I know you work a lot with large organizations and large organizations, people don't know everybody and it can be intimidating and knowledge is distributed all over. And creating that Q&A and community aspect can really be beneficial.
Building trusted AI knowledge for enterprise
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[00:06:52] Melissa Perri: That's really cool. I didn't know that Stack Overflow had a solution for internally in companies. What does that look like?
[00:06:59] Jody Bailey: Yeah it's very similar in terms of the question and answer. We've got some capabilities that are targeted more towards enterprise. We do things like, we wanna discourage any sort of, negative feedback, so we, it's not so much, down voting as more, yeah, this is good.
[00:07:18] We also help identify subject matter experts, et cetera. And, one of the things that we're working on right now that I'm really excited about is this idea of being the trusted knowledge player. We see with the dev survey, which results just came out recently, so you know, folks that are interested in the dev survey should check it out.
[00:07:39] But, we see 80% of developers within businesses are adopting or using AI tools. And one of the, one of the things that those AI tools leverage are the large language models, which are largely built on, you know, using Stack Overflow public data. And That's really useful and valuable as people are working through things.
[00:08:00] But you, within a business, you have proprietary ways of doing things. Those aren't in the large language models. They're not in the coding agents. So how do you empower the people with that information? And then, as within businesses and organizations, documentation lives all over.
[00:08:18] There could be multiple versions. Oftentimes, as soon as it's written, it's outta date. Nobody maintains it. So what we wanna offer is that trusted layer, right? So what we look at doing is ingesting a lot of that information. Turn didn't into q&A, questions and answers, to make it really easy to understand and process.
[00:08:38] But then we're also able to identify subject matter experts in the organization. When we import that data and convert it, we also calculate a confidence score, right? Is this something you know, is it new? Is it from a subject matter expert? Are there multiple copies? And then we can route that to appropriate people, make it visible for people to say, yes, this is good.
[00:09:00] Trust it or not. And then, within the stack, internal product, we have that information. Then service serve that up through a MCP server so that it can be automatically ingested and used in whatever AI tools they're using. So that's something we're really excited about. We're in the early stages, working with a handful of customers to pilot and work out the kinks, but really excited to about the opportunity there.
[00:09:26] Melissa Perri: That's really cool. When you were, thinking about introducing this idea, what signals from customer feedback were you looking at to say, Hey, this might be something for us. How did you think about that strategy and how it plays into Stack Overflow.
[00:09:38] Jody Bailey: Yeah, great question. There's a couple things, one since joining or taking over products really been focused on outcome. Driven, roadmaps and really shifting the focus from, let's deliver a bunch of stuff to let's focus on the outcomes.
[00:09:55] And then also, borrowing from Teresa Torres, the continuous discovery and all those things. So that's one aspect. But we've, we've had this internal product for a while, and one of the challenge has always been, what we call the empty stadium problem. And that's the idea that Yeah. having, stack overflow this huge, vast, wealth of knowledge is really useful.
[00:10:18] But what if you're starting from scratch? And we've had different programs and, one of the benefits of the advancement of generative AI and others is that it makes it easier for us to ingest that data and translate it. So one, it's the, we've had this demand from users and customers for a long time.
[00:10:38] And then, as we have these discussions with developers and using the tools we learn, where they're getting stuck, and then the advancement of technology and being able to apply those. So that's how we landed in that particular spot.
[00:10:53] Melissa Perri: Yeah. When generative AI first came out and you saw people like turning to Claude and to chat GPT to ask their questions, was there ever like a oh crap moment? What are we gonna do, how do we think about positioning ourselves here?
[00:11:06] Jody Bailey: I'd be lying if I said no. I think many people in many different industries had that, oh, crap moment. And I think you saw a lot of people and businesses, you think SaaS, you think other community sites, had this oh, crap moment. It's oh, we've gotta release something, we've gotta have an AI solution. And you saw this proliferation of AI tools. And, talking with other CTOs, CIOs, et cetera. One of the mistakes I think almost everybody made, which is so fundamental, is we focused on delivering AI solutions. Not solving user problems or customer problems.
[00:11:51] We were solving for, we have to have AI. And I think a lot of different companies did that and we had an experiment with that and some good things came from it. But we also spent a lot of time doing things that really didn't bear fruit, and I think it's just one of those reminders to always focus on solving problems for your users or customers and, not to just focus on the shiny object.
Redefining Stack Overflow’s strategy for the AI era
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[00:12:19] Melissa Perri: If I could go back and just replace the word Agile and escaping the build trap with AI, it'd probably be the same exact book.
[00:12:26] Jody Bailey: Yeah.
[00:12:26] Melissa Perri: Yeah.
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[00:12:57] I, but I see that mistake a lot. And the one thing that is interesting to me about the business model that you're talking about with Stack Overflow and going forward, is it sounds like you are looking at how do we position ourselves in this AI world, right?
[00:13:08] Like we see this user behavior. Where it's turning now to LLMs to ask easy questions. Where are we strong, right? What's our unique value proposition? Like, where do we shine? And you mentioned that there's a part to a stack overflow where you're looking at data licensing too. How do you think about that with the AI tools?
[00:13:25] Jody Bailey: Yeah. So it's one of those double-edged swords, right? The obviously, from a revenue perspective, it's been really fruitful. At the same time, we're also fueling the engines that reduce the traffic to our site. The things that, that we're focused on, like you said, from a strategic perspective.
[00:13:43] Always go back to what are your core strengths, right? What can you do to leverage those, what are the things within an order of magnitude or so, innovation wise, that leverage those core strengths and allow you to win. The thing that that, we believe we're good at is that human connection.
[00:14:02] It's, getting information, technical information, and so we're really focused on how do we be the vital source for technologists and with ai, I think the definition of technologist expands. So really we're thinking technology enthusiast, it's naming's hard, but if you think about any business or organization with the tools that are out there for vibe coding, anybody can build something, right? And they don't consider themselves technologists, many of 'em, right? You think about your CFO who's building an app, right? Or your HR person, they don't necessarily think of themselves as a technologist.
[00:14:41] But we believe that stacked overflow can be beneficial to them as well, right? So we're trying to think, okay, what are our core strengths? Who are the core personas? How's that expanding? So we're looking at that, and then, what we wanna do is we want to make sure that we create a space where people feel comfortable, where they can interact, and they can interact in different ways.
[00:15:05] Stack Overflow has always been focused on these canonical answers, right? The, they're questions that stand the test of time. They're unique and they've got detailed answers and they work or they don't. And that is so valuable and so important and we don't wanna do anything to break that.
[00:15:22] At the same time, oftentimes people have other questions. Maybe it's a derivative of one of those that, and we would historically close it as a duplicate. Maybe it's a homework question, maybe it's just an opinion and those things historically haven't really had a place on Stack Overflow, and we believe that there's a way to protect what we've always done while creating safe spaces for some of those other conversations.
[00:15:50] That are important to technologists and technology enthusiasts. So as we've evolved our strategy, that's really how we're looking at it, is how do we have that walled garden, if you will? Or maybe if you think of the library, the place with all the information and the research and all that.
[00:16:06] But it's really, very tightly held, and then you have different spaces for different types of interactions and knowledge, et cetera. So that's how we're thinking about the evolve strategy on the public side.
[00:16:19] Melissa Perri: Have you seen like any changes lately with the, advent of AI and these different personas that you're talking about between like the conversations technologists are having or what they care about or like where the topics are starting to stray into?
[00:16:33] Jody Bailey: Yeah, I think, we're starting to see some of them and we're also, also looking at how do we bring more of those conversations onto Stack Overflow, right? Because historically, a lot of the conversations we're seeing now might not have lived there, so a lot of the things that we're seeing now that are new is more around just.
[00:16:54] When you think about your prompt, or how do you ask a question? How do you get help with your prompt engineering? That's different than a coding question, right? So oftentimes it's not, here's the code, why doesn't it work? It's, here's what I prompted, here's what I got. I don't get it right.
[00:17:13] So I think that's one of the evolutions that we're seeing for sure.
[00:17:17] Melissa Perri: Cool. So yeah, so not just about coding, we're going into how do we interact with technology too.
[00:17:23] Jody Bailey: It's funny 'cause I talked to another CTO and talking to him about their organization and when they're reviewing pull requests, they're asking the developers to include the prompts they use to generate the code.
[00:17:38] Melissa Perri: Oh, interesting.
[00:17:39] Jody Bailey: I thought was fascinating because, one of the traditional ways of doing a technology interview is, walk me through how you would figure out this problem, right?
[00:17:49] Not necess, you do pseudo code or whatever, but at the end of the day, that's like what you're doing with the prompt, right?
[00:17:55] Melissa Perri: Yeah, that's really fascinating. That's a great way to like also see how people leverage AI tools, right? Because I feel like there is a push out there by like investors and executives of use AI so we can go faster or you should be using it to harness it.
[00:18:09] Jody Bailey: Yeah.
[00:18:10] Melissa Perri: interesting way to assess like how people think about when to use it too.
[00:18:13] Jody Bailey: Yeah. I'm really curious to see, get more information about the, how much AI is actually helping people go faster, right? Because you get so many mixed signals. I know that Atlassian did a survey recently and what they got from their users was, Yeah, a lot more people are using it, but they're not getting any increased productivity.
[00:18:37] And then you have people saying, oh Yeah, I am, 10 times as efficient as I used to be without it. And, all the signals don't lead to the same place. And so really curious to see what develops there.
[00:18:50] Melissa Perri: Have you seen anything with your engineers or with the way that you're looking at the organization where AI has been particularly beneficial?
[00:18:57] Jody Bailey: The, I think it varies. We see some people where it's really useful. I'd say the, the best place so far is really, that quick iteration and experimentation, getting proof of concepts up and rolling quickly. That's been super helpful. I think oftentimes it's the product team.
[00:19:21] That really benefits from that because they're not as dependent on the engineers to at least, create that initial version of something that, that works.
[00:19:30] Melissa Perri: Yeah.
[00:19:30] Jody Bailey: I think that's a really powerful place.
[00:19:33] Melissa Perri: I've definitely seen that trend as well. I think it's fantastic for like prototyping,
[00:19:38] Jody Bailey: Okay.
[00:19:38] Melissa Perri: something in front of somebody get some feedback early on so that you can then iterate on it.
[00:19:43] Jody Bailey: Totally. Yeah, it's, and it's pretty remarkable how much you can accomplish and how good it can look, just with a little bit of effort.
Trust, adoption, and the limits of AI in dev work
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[00:19:52] Melissa Perri: So true with Stack Overflow too, your community, a lot of it's built on trust, right? And, you have to trust that somebody's giving you a good answer, right?
[00:20:03] Or like somebody, somebody's not like just taking you for a ride and you have all the upvoting and down voting and the ways to build that trust.
[00:20:10] But how do you think about building a product that incorporates a trust? What does that do to your strategy, to the way that you think about releasing new features or adding new things and branching out into new products? Like how do you keep trust central to what you do?
[00:20:25] Jody Bailey: Yeah. There's there's so many different ways that could go there. So from a product perspective, obviously. Stack is built on trust. And that's what we're trying to provide and that's what we're leaning into. So a big part of what we try to do, is always tie it back to human interaction and knowledge.
[00:20:45] I think that's fairly unique to our problem set, the, the products that we deliver. Beyond that, some of the really straightforward things is just being transparent about when you're using AI, when you're not I think grounding anything that you, that's generative in any fact or related content, providing the annotations and where it's coming from I think is super useful. If you look at it from the other side in terms of internally, within an organization, developers in my experience are naturally skeptical and certainly. That's true when it comes to ai, right?
[00:21:28] And then you throw in the fact that, there's all this conversation about how their jobs are gonna be replaced by ai and that can create a very uncomfortable, culture, right? Or, where people are worried about their jobs. I think about it, even, on a different scale, like when cloud came out, right?
[00:21:49] And how many of the people that were, managing the data centers, everybody was worried about losing their job and or they were just skeptical that this isn't going to work. And I think that it's a little similar with AI. At the same time, if you think about cloud and how long ago it came out, and there are still companies that are just migrating to cloud, I think that, the fear that developers are going to be replaced,
[00:22:22] Melissa Perri: Oh yeah.
[00:22:22] Jody Bailey: Next year is pretty, or even within, five years. it's Overly ambitious or overly optimistic or pessimistic, depending on your view. That said, I think within an organization, trying to figure out, how to build trust with your team is super important, I think Being clear around what your intentions are, how you're going to use AI, how you're hoping to help them, help themselves is important.
[00:22:50] Providing training, giving them space to, to leverage the tools and onboard themselves I think is really important. Our approach so far is different than some you see some of the hopes in the press where it's okay, everybody has to use AI. You have to demonstrate that you're using AI or you can't hire anybody.
[00:23:08] My approach is definitely different than that. I like to build the trust, have the team, find ways that it works for them, and then integrate that into the way we do work.
[00:23:18] Melissa Perri: I think with the AI replacing developers, like that's one of the hottest topics that were out
[00:23:24] Jody Bailey: Right.
[00:23:25] Melissa Perri: I think we're so far away from that, like maybe some probably helping. Bring that up, right? If you weren't doing a lot of work around stuff or a big project. I don't see the architecture pieces or the thinking through problem pieces or
[00:23:40] Jody Bailey: Exactly
[00:23:41] Melissa Perri: Like the deep work stuff.
[00:23:43] Jody Bailey: right.
[00:23:43] Melissa Perri: us like slightly more efficient where we don't need as many people to, to help build things. But I don't think there's ever, I don't know if there's ever gonna be a time when it just replaces it, or at least not in the near future.
[00:23:55] Jody Bailey: Yeah, it's hard. It's hard to imagine. There are times when I'm at conferences or talking to other visionaries and they'll show things and you know, it's easy to get swept up and it's like, oh my gosh, yes, you're right. You know, It's gonna be two developers and a thousand agents, but then you come back to reality and it's like, okay, Yeah.
[00:24:16] Not yet, not, I don't, you know, you see a demo and it's like, oh wait, that didn't work. Um,
[00:24:22] Melissa Perri: And there's so many of those out there too. I think there's so many people putting out products and it sounds great in theory, and then you get in there
[00:24:28] Jody Bailey: yeah.
[00:24:28] Melissa Perri: and it's it just doesn't work
[00:24:30] Jody Bailey: Right, right.
[00:24:30] Melissa Perri: the way that they promised it.
[00:24:32] Jody Bailey: Yeah, exactly. And then, there's that hype train and often as senior leaders it's easy to get sucked into that, and you have to be careful not to, and to make sure that you're focusing on the real benefits and challenges and opportunities.
[00:24:47] Melissa Perri: Yeah.
[00:24:47] Jody Bailey: But to your point, again, talking to, I think a lot of the senior engineers get, can get more value, as they learn how to use it. And one of the things, one of the strategies, I've heard from senior developers is around breaking down these complex problems. And then just using the generative AI for the smaller pieces, as opposed to trying to build the whole solution.
[00:25:11] The challenge there is that works. If you've got the experience and understand how to break things down, right? But if you think about a junior developer who's coming in and trying to build something and it's, they can just prompt up the whole thing, all of a sudden, they get stuck and they don't know where to go.
[00:25:30] So I think that points to the fact that you do need. The experience you do need, the people that understand system thinking in order to really leverage it.
[00:25:40] And I think if you can combine those two things, that's where you're gonna get, the most bang for the buck.
[00:25:45]
Keeping junior roles relevant in an AI future
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[00:26:08] Melissa Perri: There's been a lot of talk too about how AI might replace those junior level roles, right? Whether they're developers or product managers, because it can write a spec for you. Why do I need somebody to like, spec out everything and put it into Jira? With the developers, it can do the little code tweaks.
[00:26:24] It can do all these small pieces like you were saying. do you think we that one day we still have senior developers, right?
[00:26:32] Jody Bailey: Right.
[00:26:32] Melissa Perri: never have a junior developer, we'll never have a senior developer, same with product managers.
[00:26:36] Jody Bailey: Yeah.
[00:26:37] Melissa Perri: How do you think that's going to work out in the future, and What do you think we can do now to ensure that we don't just lose our whole junior workforce, which we'll need in the future to run
[00:26:48] Jody Bailey: Yeah. I think there's a few things. One, from a hiring perspective, I think you need to be deliberate. And I That's true today, right? It, you see it all the time. When you can only hire X number of people, whether it's product or engineering, it's okay, I've gotta hire a senior person because I need to get the most bang for the buck. in reality, most of the time it doesn't work out that way. It's really the combination of skills that, that provides the most bang for the buck. It's I think of it as a team sport, and if you, if everybody is the star, then nobody's doing all the other work. And how do you create that natural evolution?
[00:27:27] So I think, being deliberate about it is a big piece from a product perspective at Stack Overflow. One of the things that I think is important for us and other, online education or AI tools, is to help create, an education process, right? Where you can explain the why. Not just generate a bunch of stuff and, hope it works, but help people understand how it got there.
[00:27:56] Be able to look at, code or whatever, explain it and really, provide that kind of information. The third thing I'd say is that I think it's important for people that want to be, senior product leaders or senior engineers, is that they understand the work they're doing, that they invest their time to understand, if the specs being written, okay, what, what are the components of the spec? How might I get those answers? Do I trust the data that generative AI is providing? Where did it come from? It's, one of the most important things I think, for being a product manager and product is that curiosity, right? And being data driven.
[00:28:36] And I think that, when you bring somebody on, you can bring somebody Junior to use the tools and then it you have, if they want to be successful in the long haul, they have to invest in themselves. They have to understand they need to do the work, not just rely on the outputs.
[00:28:55] Melissa Perri: Yeah. And with that, it sounds like there's some traits to look for in there, right? We, you mentioned the curiosity part about the product management, but there's also like this judgment piece or this, like poking on how to get the
[00:29:06] Jody Bailey: Right.
[00:29:06] Melissa Perri: underlying factors. When we think about teams, right? Like we have our senior people there and we're bringing on these junior people, they're gonna be using the tools.
[00:29:14] How could more senior people support those junior people to make sure they actually are learning the why? What should they encourage 'em to do? What should they be looking for? Trait wise to make sure that they're learning that judgment. They're learning about that why behind it. Like how do you make sure somebody's not just like sitting in a corner typing away.
[00:29:32] Jody Bailey: Yeah, no, that's a great point. I think one of the things, and it's, it seems simple is, talking to users, right? Talking to customers, really, developing those empathy skills and understanding why what they're doing is important and how it's going to contribute.
[00:29:48] I think at the same time, it's also, having those conversations, going back to the. The connection between the senior and the junior person to, help develop those skills. So there's, I think having mentors, mentorships, all those things are super important.
[00:30:06] Melissa Perri: In Stack overflow, you are also the CPO. Can you tell us a little bit about how did you take on product? What does your team look like and how do you think about managing from both like a CTO and a CPO perspective?
[00:30:19] Jody Bailey: Yeah. Yeah. So I'll back up a little bit. Throughout my career, it's always been, I would say, somewhat opportunistic, right? Meaning when I was a developer, I didn't think about, I didn't, I didn't aspire to be CTO, right? It was like, okay, I'm a developer and then well, how can I contribute more?
[00:30:39] And okay, I became a manager. I don't wanna, I don't wanna be, a director or vp. And then it's just always been let me do what I'm doing, do it as well as I can, and then how can I have more impact? I can't say that I aspired to be Chief Product Officer any more than I can say I really aspire to be Chief Technology Officer.
[00:30:58] However, one, the product that we build is largely for technologists and developers. I've always been curious. Or I won't, I can't say always. I'd say over the past 10 years I've been very curious about product management and I feel like I've worked with some really amazing product leaders that were really inspiring and I've, had the opportunity, I mentioned I got to see you speak Teresa Torres, Nate Shaw, a number of folks and it's been really interesting, and our chief product officer left at the end of last year.
[00:31:33] So we had an opportunity and I raised my hand because I thought, okay, this could be a really interesting and fun opportunity and frankly, stack overflow with everything That's been going on with AI, everything else. It's really an inflection point. And the other thing about me is I like a challenge and I feel like this is a challenging point in time in terms of, how do we adapt and really serve technologists and technology enthusiasts around the world? And so yeah, so I raised my hand and said, Hey, I'd like to do this, and here I am.
[00:32:11] Melissa Perri: That's very cool with the like with the mantra of Stack Overflow too, with it's for technologists. You don't say developers specifically. Do you ever see product managers hanging out on there?
Internal transparency and advice for ambitious leaders
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[00:32:22] Jody Bailey: Yeah. Especially, as vibe coding's coming, I think you mentioned you, you've spent a little bit of time on Stack Overflow. So
[00:32:29] Melissa Perri: Yep.
[00:32:29] Jody Bailey: I think, it's. Not just developers it's anybody that's doing anything with technology, whether it's HTML and CSS, whether it's vibe coding, we have a broad range of sites beyond just Stack overflow, it could be formulas in Excel, right?
[00:32:45] It's anything technology adjacent. And even, if you look at our internal product, the stack internal, oftentimes it's used by other groups, even outside of technology, so one of the, one of the things, and it works for us, maybe not every business, one of the things I like is, we can use our internal stack overflow to provide information about our product and sales can see it there, rather than, having to tap somebody on the shoulder. So it's also a good radiator for information within the organization, from the technology side of the house.
[00:33:20] Melissa Perri: Oh, that's cool too. So it sounds like you are you mentioned sales, being able to look at it. What kind of information do you share, between product and technology and sales, and how do you incorporate them into the flow? Because that's always been one of those friction points I feel like where we wanna lock everything away and not tell sales to
[00:33:38] Jody Bailey: Right.
[00:33:39] Melissa Perri: oversell things.
[00:33:40] Jody Bailey: Yeah. And I relate to what you said very much. 'cause I tend to be a little cautious, but we're, at least within Stack Overflow we're pretty transparent and, I feel like we've got a really good partnership with our revenue organization and our CEO is also, pretty careful not to sell too far ahead of product. So we, we have roadmap information, but there's also, information about different innovation work that we're doing, experiments that we're running. I've used it as a way to share my, you know, like what are the things i'm working on this week, kind of thing. So we're pretty transparent. There. But it is always a delicate balance between, Yeah. we think we can do this and, being careful that it doesn't get sold before, before you've figured out whether you can or not.
[00:34:32] Melissa Perri: Have you put any like guardrails in place or structures like between sales and product to help prevent those things?
[00:34:39] Jody Bailey: I don't know that I would say anything unique, right? We leverage a lot of the common things? So we have, weekly business reviews. We have, roadmaps that we share that are more public facing. And we have, we have also internal things as well that maybe aren't. As broadly advertised, so if we're running an experiment, especially if we're experimenting with different technology, we may mention it but not document it, if that makes sense.
[00:35:10] Melissa Perri: Cool. Yeah, that does. So Jody, when you look back on your career, you've done so many different things: Pluralsight AWS, and now Stack Overflow. Just among a few. What is advice that you would give to your younger self?
[00:35:23] Jody Bailey: One of the, one of the things that, that resonated with me early on and when I talked to people and, as they're trying to work through their career, one of the things that I. That I believe is, and it's really simplistic, but I used to have it, it like, it was an article from an internal I've worked at, it was Fidelity Investments way back in the day.
[00:35:45] And somebody had said this and it was, it just resonated with me and it stuck with me. And it's if you work hard and focus on the right things, things will work out. And I think oftentimes, people want to do something different. They wanna get promoted, they wanna take, have different responsibilities and they just want it to be given to them.
[00:36:08] And my experience is that, you are able to broaden your influence to get new opportunities by doing a little extra right. And doing some of the things that you want to be doing, rather than just asking if you can do them. And my, my advice typically is just, you've gotta, you gotta put in the effort.
[00:36:29] If there's something you want to do, figure out what it is, figure out what needs to be done, create the opportunity. The other big thing is being clear with your leadership what you want, right? So there was a point in my career where I was working at a company, I was VP of engineering and there was a CTO opportunity open. And I was helping interview for the CTO. And I'm interviewing all these people and I'm like, why are they not, I have more qualifications than these people. Why? Why am I not being considered well? And then I finally, as we're narrowing in on somebody, I finally talked to the CEO and he's oh, I didn't know you wanted the job.
[00:37:06] I figured you would've said something. And so I think that's important too, right? Is if you are aspiring towards something. Make sure your leader knows so that they can help create the opportunities so that they can steer you in the right direction. It's really, it takes both sides to really make it happen.
[00:37:26] Melissa Perri: Yeah, that's a great reminder. You're not gonna get it if you don't ask for it.
[00:37:29] Jody Bailey: Yeah, exactly.
[00:37:30] Melissa Perri: Jody, it's been such a pleasure having you on the podcast. If people wanna learn more about you, where can they go?
[00:37:35] Jody Bailey: Oh, LinkedIn's probably the best place for me.
[00:37:38] Melissa Perri: And we will put your LinkedIn URL on our show notes at productthinkingpodcast.com and we'll also link out to Stack Overflow so everybody can
[00:37:46] Jody Bailey: Awesome.
[00:37:46] Melissa Perri: follow the great work that you're doing. Also, stack Overflow is running an experiment for you to check out, go to stackoverflow.ai to see the new AI first interface and communicate with all of the community on there.
[00:37:59] Thanks again for joining me on the podcast, and thank you to our listeners out there. We'll be back next week with another amazing episode.
[00:38:06] Please tune in, make sure you like and subscribe so you never miss an episode. We'll see you next time.