Pendo CEO Todd Olson On How AI Is Redefining The Product-Led Organization

[00:00:04] What does product-led growth actually look like when you're operating at real scale? Not as just another buzzword, but as a very real business model. Well, today it's time for me to sit down once again with Todd Olson, CEO and co-founder of Pendo. And together we're going to talk about what happens when product becomes the primary growth engine.

[00:00:30] Because here in 2026, Pendo now tracks trillions of user events across 2,500 customers. And Todd has had a front row seat at how SaaS has evolved through zero interest rate eras to the AI wave that we find ourselves now. And what some are calling the great reckoning for the software industry. But we will talk today about how to turn overwhelming volumes of product data into meaningful insight.

[00:01:00] How AI is accelerating experimentation inside product teams. And why measurement, continuous improvement still matter in a world obsessed with automation. And he also argues that we will start to crave originality, creativity. So much to go to talk about today. So will originality become the most valuable asset in an AI saturated world? Are you getting tired of seeing too much AI slop and craving more originality? Maybe you are.

[00:01:30] And if you care about scaling software responsibly, building durable companies and staying relevant through multiple technology cycles. Well, this conversation will cover it all today. We've got a lot to get through. So join me in welcoming Todd right back onto the podcast now. So a massive warm welcome back to the show, Todd. We first spoke way back in 2018. This is your fourth appearance.

[00:01:56] But for anyone that have missed our previous conversations, can you tell everyone listening a little about who you are and what you do? Yeah. Thanks for having me, Neil. It's great to be here. So I am Todd Olson. I am the CEO and co-founder of Pendo. Pendo is a 12-year-old software company. And our focus is actually really simple. It's to help make sure that the software that gets created actually delivers on user needs.

[00:02:23] And in a world today where people are now able to generate software via very simple prompt, Pendo measures, optimizes, and help people fully take advantage and get value of all that software. And going back to your origin story, I mean, you founded Pendo back in 2013 with tech royalty. You got veterans from Red Hat, Cisco, and Google back in the day.

[00:02:47] So when you strip away the buzzwords, all these years later, what does product-led growth actually look like inside a 750-person company serving 2,500 customers? Yeah. Yeah. Yeah. Well, the good news is we're seeing product-led growth all around us all the time right now. I mean, this is like one of the, you know, what's product-led growth is when users, customers are able to interact with products in a more self-service manner.

[00:03:14] And they get sort of so addicted to it that it creates a viral loop where people start using it more and then ultimately start paying for it. So it's leveraging the product as sort of the apex of the growth engine and relying far less on human beings. So that's kind of like ultimately at a high level what we think about is how does the product deliver the experience and, again, rely a lot less on human beings.

[00:03:42] And for people that don't know, Pendo, you track trillions of user events to guide product decisions. So how do you turn that scale of data into action without overwhelming teams or drifting into analysis paralysis? Because you can have too much of a good thing sometimes. I would imagine AI has made that world a little bit easier, but tell me more about that. Yeah. No, I think that's a great question.

[00:04:04] And yes, we do collect crazy amounts of data, but then it's all about how do we take that data and then start organizing it in a way that sort of reflects the state of the application and put it in terms and words that are actually very meaningful to the end users. So you can organize that data into things like what are my core pages or areas of my product? What are my core features that people are using or trying to adopt? What are key journeys?

[00:04:31] People going from point A to point B to point C and then where is there's drop off amongst that? When you start servicing things like there's drop off here or we have really good adoption here but really poor adoption there, that's when you start to glean insights. You know, we've started to do a much better job of sort of surfacing, you know, what I would call outliers, big variances or changes. That's often where the insights lie. It's like, okay, I did some work.

[00:05:01] My team did some work. We published something out. The product either got dramatically better or dramatically worse. That's actionable, right? That's actionable, right? So the question is that I think fundamentally your question is the right one is how do we go from just raw data to actual insights? And, yeah, you also mentioned that AI is making this easier. So we are now delivering capabilities where you can just ask AI, what should I be looking at?

[00:05:30] And it has all of your data accessible via tooling and it could start to highlight things. Hey, we think you should look at that or, hey, we think you should look at this. So, yeah, I would almost think of it as an AI data analyst. Just now it's included out of the box within Pendo. So that – and I think it's still very early days on that technology. We're going to get smarter and better and better. And, you know, we go over time.

[00:05:56] I imagine a day where people just simply wake up and, you know, log into their Slack or other means and they get – they say, oh, you know, Pendo's pushed me three things to look at today. I should go take a look at it. And you click into it and learn a little bit more. And that's kind of a lot of the work that we're working on now is how do we just push to you the right things that you care about? And I think that it's a really important distinction because whenever we think about an insight, it has to, one, be contextual to the business. So what's the business going through?

[00:06:25] It means contextual to the team. What's my team going through? And then what do I care about in that team? And then we think of all three vectors when we think about insights. And the world has changed so much in the last, what, six years. We went from the global pandemic working from home at scale, hybrid working. Then AI came around. And you wrote a book called The Product-Led Organization. I think it was something like around 2020, correct me if I'm wrong, which was around about that pandemic time.

[00:06:53] But looking back now, what did you get right about the movement? And where do you think the industry is misunderstood or, again, maybe even oversimplified the concept? Yeah. Well, first of all, I think that the concept is as relevant today in 2026 as it was back in 2020 when I first published it. I think some of the examples may be a little bit outdated because there's been a lot of change in the last few years. But I think the concepts are dead on.

[00:07:21] One, I think this concept of the product-led organization where the product itself offloads a lot of work from the business, and particularly humans, is what we're seeing in the market today. We're seeing it almost in extreme forms.

[00:07:40] And that's everything from, I mean, you're seeing these companies have incredible growth, at least on the top line in the revenue, but they're not growing their headcount internally at the same scale. So, okay, so who's doing the work? Well, the product's doing the work. That's where most of these AI companies, we're seeing like ultra efficiency, not adding as much headcount, but still growing at really remarkable speeds.

[00:08:06] These are actually, these are step function better product-led organizations than what the prior era had created. So I think that is what AI is unlocking. AI is making it easier for every company to be a product-led organization. So now you're inspiring me. I need to update my book because there's no question. Like, I think it's, again, as relevant. Almost every chapter is relevant. The big difference is you can do it at just grander scale faster. You know, I have a whole chapter around running experiments.

[00:08:36] It's like, wow, you can experiment really quickly now. You know, so content experimentation in the book was a great concept. Just the tools and techniques and how you do it. It's like, it is like nirvana for people who live, read that book. So I think, I feel really, really good about that content. And look, I also think that analytics and metrics and data is just as important.

[00:09:00] And that, to me, is the message that doesn't get told enough today. It's, yes, AI is amazing. Yes, it does a lot of automation. But you still need to iterate on whatever it is you're building or delivering. Like, nothing's going to be right the first time you deliver it. And you're going to have some issues. And if you're not measuring it, you're not understanding what those issues are, you're not going to make it better. And so, like, well, I think you see this mix of AI is changing everything, headlines.

[00:09:30] And then you also see some of the counter headlines around, you know, certain projects fail this percentage of the time. And, like, you see sort of the doomsdayers as well. I think if you just release a bunch of technology and you don't measure it, you don't focus on a culture of continuous improvement, it's not going to be great. Right? Yeah. And I think it's the message we need to continue telling because AI isn't, like, a magical unlock to make things great.

[00:10:00] You still need to, like, do the work. And I think the book talks about that, but I think that's really important now. And elsewhere, there's also a growing talk about the reckoning in what many call the software industry complex. So from your vantage point as a, what, three-time founder now, what are you seeing changing in SaaS economics? And what needs to be rebuilt, do you think? Yeah, no, this is a really interesting thing. And I think I have a unique vantage point.

[00:10:28] You know, I started my career at age 14. So that makes me probably more than 30 years actually developing software. And fun fact, at age 14, I was working in an IT department that was building custom apps. It would have been the natural areas where you've been using AI, you know? And then I've since then worked at software companies, which provide professional apps that then those companies buy.

[00:10:53] And you've seen throughout that 30-year period this sort of, you know, custom versus packaged flip-flop a lot. And clearly, we're in the custom, you know, we're in a custom era right now where everyone's like, whoa, I can, like, type in a lovable and get a prototype. Why would I need to spend all this money on Workday? Well, I will say there's a reason why Workday and companies like that exist.

[00:11:18] Like, you know, like, while it's really cool what you can build quickly, like vibe coding, your payroll has, you know, lots of implications if you get it wrong. There's a lot of compliance issues, which, like, eventually the tax of just keeping up with the software will get, like, overwhelming. So I do think this sort of, I think we're going to have software applications. We're going to be buying software applications. Does that mean all software applications survive this sort of reckoning?

[00:11:48] No. No. Some things are, like, pretty basic stuff. They don't solve super hard problems. I don't think those applications are going to survive, right? Right. So I think we got to a point where we had ZERP, which is zero interest rate period, where there's so much funding, is that a lot of software companies got created during that time period that, you know, likely shouldn't exist. So you will see a reckoning of some of those businesses.

[00:12:17] But the great businesses, the ones that solve really hard problems, I think they're going to be fine. But they're also going to have to change the way they're working. Like, if you're being, everyone's going to have newer competitors, which are more modern feeling. They're newer. And they're going to be coming after some of the incumbents because the incumbents have validated that an addressable market exists in certain problem domains.

[00:12:44] So I think the other thing is we're seeing new competitors come on the market. But this is, go back. We saw SaaS competitors take on every on-premise competitor. And guess what? But some on-premise competitors were, you know, or incumbents were able to make the transition and retain their customer base. Some weren't and got disrupted. Really, that's simple. Yeah. So, I mean, let's use an example. Like, you know, Seba obviously got disrupted by Salesforce.

[00:13:12] They didn't quite make the change as quickly as they wanted. But, you know, Atlassian was an on-premise software company for years. And now it's fully cloud, right? And now I think I would not bet against Atlassian becoming fully authentic. You know, they've already made the transition once. So, like, we have lots of precedents for understanding what's going to happen. I think great companies are going to find a way to transform. 100% with you. And as I said at the beginning, we've spoke many times over, what, eight years now.

[00:13:40] And Pendo is headquartered in Raleigh, North Carolina. And I'm curious, one of the things I've been meaning to ask you is how is building outside that traditional coastal tech hub, has that shaped your talent strategy, your culture, and long-term ambition? Anything that you'd like to report on there, especially for the startup founders listening, because you're doing things a little bit differently and excelling as a result? Oh, yeah.

[00:14:05] Look, I think, obviously, being in Raleigh has been a part of our identity since day one. And look, I've always said this. Being in any location, geography, there are going to be pros and cons. Pros and cons. And now we're seeing some of that error. I mean, look, there's no question that a lot of the most AI-forward companies and human beings are in the Bay Area right now. The Bay Area has had a resurgence over the last few years.

[00:14:32] So certainly, I think, during COVID, you'd argue the Bay Area, people were fleeing, there were issues. Like, just generally read the news down on San Francisco. Now everything's very up on San Francisco. This is the place to be. And I do think we miss out a little bit on not being there. I'm not going to lie. We do. But this is not unlike the go-go days of SaaS, when all the great SaaS companies, or the early SaaS companies, were there, and you felt like you had to be there.

[00:15:02] Now, look, the good news is I can get on a plane, Neil. It's not that hard. You know, five hours away in direct flight, and I'm in San Francisco. So I can meet those founders. I can spend that time. I mean, we need to make the investment, but you can do it. And I think that's the key if you're in an area not San Francisco, is you need to make the investment, and you need to spend, like, substantive time there. So you kind of understand what the heck's going on. Like, you're not going to learn by sitting, you know, on your couch in your living room back in North Carolina.

[00:15:32] You need to get out there and go visit people. So that includes, like, New York City is also probably a little more on the forefront of talent and people. And because of this, we have an office in San Francisco and New York. So we want to be able to, you know, hire people in those areas, which, again, like, are being surrounded in, you know, a different environment. Now, having said all that, I've always said the benefit of not being there is not being in the echo chamber enough.

[00:15:59] I think sometimes the folks out in the area only hear themselves, and they don't think about the rest of the world to the same degree. And it also can be a little bit, frankly, jarring to not just be surrounded by AI, you know, in your day-to-day life, but then, you know, going to dinner parties at night and, like, being barraged with tech and, you know, agents taking over the world. And, like, I don't know about you, Neil. I need a little bit of a break in my evenings and weekends.

[00:16:27] And at least by hearing about it, like, I don't mind working. I actually like working on the weekends. But I don't want to just hear about it constantly. I want to be processing my own thoughts. So I think having separation has benefited Pendo since day one. And I think it benefits us today. And we have to make that investment. Like, my recommendation to any founder or not in one of those areas is to visit. Often as you feel like it's valuable and force yourself to do it, it's easy to, you know,

[00:16:56] be insular, get out there. That is my, always my, it's always been a recommendation, get out there. And I will say, I didn't get out there as much during COVID because it probably wasn't as important. And frankly, if I went there, I couldn't even leave my hotel room. So there were reasons not to, you know, visit then. But go there now for sure. It's back and then it's open for business. Well, you certainly seem to have got the balance right. It's an exciting time for you. 356 million raise and IPO readiness on the horizon.

[00:17:22] So how are you thinking about timing market conditions and the trade-offs between staying private in one hand and becoming a public company in the other? What are you wrestling with here? I'll be honest. I'm not thinking about it right now, which is kind of liberating. I'm not thinking about it. I think thinking about it, I probably thought about it too long, you know, you know, a few years ago, it's like, there was this sort of like run up and path and everyone was doing it.

[00:17:49] And, and, you know, I think we, we definitely are of the sort of characteristics benchmarking of a company that certainly within the 2021 cohort could have gone public. But look, most of the companies on public in 2021 are trading below their, their listing price. So like, would that be a better outcome for us? Probably not. You know? So I, I, I think, um, so I, I, I treat kind of every, every challenge is an opportunity.

[00:18:17] And I think, I think we're in this unique place where as a private company, we can really invest in our future and help create and almost transform the business to what we think it will become in the next few years. Kind of going back to this, is our software company is going to survive or not. We clearly want to be one of the ones that will, but we know we need to change the way we're operating. So we're investing heavily and like re-imagining our products.

[00:18:41] We're investing heavily in how do we use AI internally to, um, have a far more efficient go to market, just like we're seeing in these AI native businesses. Right? So we're, we're doing the work now. Will that ultimately lead to financial success? We're hoping we believe so. We believe so. I think the other thing, the point is each time you and I talk, we're just a little bit bigger. I mean, in some cases, even more so bigger, but we're not a small business anymore in terms of revenue skies and scale.

[00:19:10] And I think that's appealing as well to all markets because there's just a durability of revenue and yet bigger, you know, the bigger are, it tends to be more attractive to some of these traditional investors and we just keep growing. So as long as we keep growing, I think we have this opportunity to reinvent ourselves. As we do that, we'll weigh, you know, various financial options and see what's best for the business. But I, I'm not, I'm, I'm thinking about how to reinvent ourselves every single day.

[00:19:36] I wake up with a new energy around our products or on this technology. I'm using them nonstop. Like, um, I'm almost addicted to it over the weekends. Like I'm so, I'm having so much fun. So I think, I think that's what I'm thinking about. And I know if I do that, good things will happen. Yeah. Yeah. A hundred percent with you. And you mentioned vibe coding early in our conversation. It's something we're hearing more and more about at the moment.

[00:20:03] So when we talk about vibe coding and AI assisted development, how do you see AI reshaping product teams, especially in large enterprises that rely on things like governance and reliability and things seem to move a little bit slower. How do you see it reshaping things here? Oh, I think it's going to completely reshape everything. I fundamentally believe it. And, and, um, I, I, like I said, I've been doing it myself now, you know, working with AI code generators, things like that.

[00:20:31] And I, I'll, I'll, I'll step back for a second. I think the word vibe coding while was cool is definitely, um, um, I think a misnomer and maybe creating some of the confusion because when it sounds like vibe coding, it does not sound like professional quality software. And look, some people are building things that are not professional quality software and you have, you have non-software creators who literally don't know what the code does, but just typing it. Wow. I have a working application.

[00:21:00] I do think that's a class of apps, but I'm also seeing AI code dinners fix like real bugs, like real product development, pull, you know, tech deck tickets and like complete things that honestly it would have taken a human far too long to do. And we just wouldn't have done as many. So that means quality is going to improve over time. Now, look, does that mean that we're going to run AI against our code base and let it like check in code unchecked by human? No, no.

[00:21:26] Like every, every, I think the bottleneck we're seeing is we do need humans to review things as reviewing things. We're going to have to teach the AI. No, this isn't the right pattern to do that. Or, oh no, that's a really bad practice. And I think, so a lot of us are going through this practice of like building in our, our architectural guidelines, our product knowledge, just our standards around security, things like that

[00:21:51] to make sure as the code generators run, the code that gets generated is, I mean, I don't think I say as good as our humans would write, but in line with our standards and practices. And, but no, I think this is going to be the norm. I think it's absolutely going to be the norm. Now, what does it also mean for like sort of like existing incumbents? And I think the biggest challenge, this is what we see even, is that you need to, a lot of the AI doesn't work great on legacy code bases. It hasn't been trained as much on some of the older programming languages to use an extreme example.

[00:22:21] I don't think anyone's going to be using cloud code on COBOL. Now, look, I say that, I'm sure someone probably has figured it out, but, but broadly speaking, what we're seeing like AI on legacy code bases is harder. So what does that mean? Well, can you refactor? Can you rebuild? Like, like what if we just, like, I think more time is going to be on teaching AI about legacy code bases or refactoring the legacy code base to be using a new technology. So it can be used.

[00:22:49] That's how we're thinking about the problem a lot. And, but yeah, super interesting time for that. Well, once again, we've talked about just how much our world has changed in the last five years, even 10 years. And I've got to ask if I was to take you way back to the beginning, if you were starting Pendo again with today's technology and AI saturated capital conscious environments, what would you do differently in the first two years to build a product led company that lasts?

[00:23:19] Because the way you did it then and the way you would do it now would possibly be quite different, but I'm curious how you would approach it now. Wow. I love that. You know, I'll maybe I'll have a hot take. I don't know that I would have approached it very, very differently. Uh, yeah. Like, like, like in terms of like now what would we've done day to day would have been wildly different, but look, go back to the beginning. You know, um, I always say when you're a tiny company hire for pain, I think with all

[00:23:46] the say, I told us you'd have different pain, you'd have different pain. So I would have hired different people. I wouldn't have hired the people I hired at the beginning, but I still would have had the same philosophy of hire for pain. I would have obviously, I think everything would have been faster. I think, I think two years would have been more like four in terms of what we're able to do. Um, I honestly think we could have grown that much faster because you think about just like, you know, there are periods where we had to like refactor and fix things that took months.

[00:24:14] I bet you would make a week now, like a week. Um, yeah, the tools, technology, I think all that, I mean, we could have tested so much faster and so much earlier. I think, I think it just, we would have gotten to like maybe four and maybe half the time is, is, is extremely, but I think we've done three years working too. I honestly believe that. Yeah. I bet you our head count at the end of those two years would be less, less than what it was. Um, at Pendo, we ended the second year, uh, roughly 70 ish people probably.

[00:24:44] I bet you would have 30, 30 and maybe bigger in terms of revenue. That's what I believe. But like, how do I approach it? I mean, I think I would approach it exactly the same, you know, like fighting for product market fit or iterating, measuring, um, build a great product that solves a real pain. Like that's still the core of it, you know, and in a world where you can divide code anything, what are the real problems that exist?

[00:25:10] You know, I, I think founders need to realize that's the interesting part now in AI I'm sitting in front of this prompt. I can type anything. What's an interesting thing to type? Like, what are the actual problems? Where are people struggling? I think, I think product management, understanding your users is even as a, not as a, it's always been important. It's even more important now. So, um, but I, I, I, you know, I'll be honest, I think we thought it was important back then. I still think it's important.

[00:25:39] So like that, in that sense, nothing, nothing would really change on how I'd start things. So. Yeah, I absolutely love your answer there. And I think if we, we talk about technology all the time and AI, this AI, everything, but fundamentally it comes back to build a great product, solve a real problem. Absolutely love that. And I'm going to give you an opportunity now to stand on my virtual soapbox that I bring out now and again, and allow my guests to take a stand on there and maybe bust a myth

[00:26:08] or misconception about something that you repeatedly say, whether it be on LinkedIn, Reddit, wherever you hang out, you probably see a few things that might frustrate you or trigger you somewhat. Is there, is there any myths or misconception we can lay the rest today about the industry at all? We already talked about software being dead or SAS being dead. I think that's. Yeah. So I, I, I don't agree with that at all. Um, but then, you know, similarly, you know, I just sort of talked about it, but product management, I've heard product management's dead.

[00:26:36] We're not going to need product managers. Look, I think product manager is going to evolve. And I think now understanding what your users want and what you need to build. Well, that's fundamentally the hardest problem people have. And yeah, does that, does the role of product management and like the, the type of product manager you hire differ in the future? Yeah. I, I, I'm already talking to companies where people are renaming their product managers,

[00:27:02] product engineers, implying that they can go right from sort of an idea to working code. Um, I've seen similar things for design and UX where people are creating working applications rather than just mock-ups and, and, and drawings. So, but I think those, those, like you're staring at a screen and it can, it can work in your infant number of ways. And now it's simply a matter of a prompt to tell to work differently.

[00:27:28] Like having style and taste and design is critical, more important. You know, I, I mean, you're in the content business, Neil, like, like if an AI robot could just iterate through and ask a bunch of questions and follow a script, would that be you? Would that be unique? Would it be original? Yeah. I think, I think my hot take, I should probably tweak this. I meant to tweet it, but like, I think originality is going to be the most interesting asset that

[00:27:56] we have as a culture, like, cause we're going to just crave original thinking, original writing, original things. And we get AI slop, whether it's content or software, we're going to start to reject it. And we're going to start to crave craft items that feel like someone built it with love and care and attention and an opinion. You know, I think that's, that's, that's, that's the future. So, wow. And I think that is a powerful moment to end on.

[00:28:25] And Pendo, you aim to support the success of product and digital leaders around the world. There's going to be a few of those listening today. So where can they find more information about anything we talked about today? Learn more about Pendo, your journey, your books, so much going on there. Where would you like me to point everyone? Yeah. Best place is our website, www.pendo.io. Of course, we're on LinkedIn and other places as well, but our website will have it all. So. Awesome. Well, I'll add links to everything and I'll encourage people to check that out.

[00:28:54] Feedback on anything we talked about today, but a pleasure as always, my friend. Just thank you for sitting down with me once again. Appreciate your time. Thank you, Neil. What I loved about Todd is he remains so grounded despite the scale that Pendo has reached over the last decade. And he keeps coming back to fundamentals, build a great product, solve a real problem, measure what matters, improve continuously.

[00:29:20] It's like a real breath of fresh air for me going back to those fundamentals. But at the same time, he's very clear eyed about the AI changes. Product teams can move faster. Refactoring can happen in weeks instead of months. Headcount and revenue are no longer scale in lockstep. But none of any of this replaces judgment, taste or understanding your users.

[00:29:46] And perhaps the most powerful takeaway is that idea that in a world flooded with generated content and generated code, originality, craft, thoughtful design, human creativity. These are the things that could become more and more valuable. And I think Todd might be onto something here. But over to you. If today's episode sparked any ideas in you, whether you are leading a product team, building a SaaS company, or just thinking about your next venture,

[00:30:14] love to hear what you believe will separate the companies that last from those that fade into the next chapter of software. Let me know, as always, techtalksnetwork.com. Remember, I've got a lot of events coming around the world from Abu Dhabi to Austria, US and everywhere in between. So please check out that over at Tech Talks Network. If you're going to any of these events, please come over and say hello. But that is it for today. So thanks for listening as always. Speak to you tomorrow. Bye for now.

[00:30:42] Bye for now.