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Trisha Price: If you build software or lead people who do, then you're in the right place. This is Hard Calls, real decisions, real leaders, real outcomes. Hi everyone. Welcome back to Hard Calls, the podcast where we bring the best product leaders from all around the world to talk about best practices, tips, tricks, scaling lessons, and of course the Hard Calls they've had to make.

Trisha Price: Today we're mixing it up a little bit and we are live from Pendo's headquarters in Raleigh, North Carolina, and I am with the co-founder and CEO Todd Olson. Hi, Todd.

Todd Olson: Hey, Trisha. 

Todd Olson: How you doing? 

Trisha Price: Good. Good, good. Well, as you know and the listeners know, we always start Hard Calls with talking about a hard call you've had to make.

Trisha Price: But before we jump into that, I want everyone to get to know you a little bit and how we work together a little bit, and then we'll get into the hard call. 

Todd Olson: Sounds good. Sounds good. 

Trisha Price: So. For all of you guys, I was hired as the CPO here at Pendo [00:01:00] about four years ago when Todd hired me in, and I often get the question.

Trisha Price: How is it to be a CPO and work for Todd? Most of you probably already know Todd is one of the top product thought leaders, has been a product leader for most of his career before coming and founding Pendo. He wrote the book on being product-led and so obviously being a CPO and working for someone like Todd can probably feel intimidating to many people and they often just ask me like,

Trisha Price: How did you find your footing? How was it to work with him? So I'd love for you to just share like what your thoughts are on bringing in a CPO and how that, how that works. 

Todd Olson: Well, first off, I think very few things intimidate you. So I, I think, you need to find someone who comes from, is cut from that cloth that, I mean, obviously if I'm speaking to someone and they're intimidated by me, it's just gonna be a bad relationship from the start.

Todd Olson: I mean, I don't think any relationship in life is [00:02:00] positive where like one person is intimidated or has issues with the other person, especially not a leadership position. But look, I, I think you want, and I think you did this well, is you wanna find someone who wants to partner with you. Yeah. Who doesn't try to like box you out, shuts you out, rather finds a way, in a very healthy way to sort of make room for you within the org. I mean, reality is running an org at scale - there's a lot of things I probably don't wanna do, like a lot of things I don't wanna do. A lot of things I didn't do. 

Trisha Price: Career frameworks and ladders 

Todd Olson: But even like the details of execution around a lot of like, which team specifically?

Todd Olson: Like no one wants me in that sausage making. Yeah. And heck, I don't, I doubt you were even in that sausage making, you probably had one or two levels beneath you doing it, and you're providing, of course, accountability and oversight and leadership to all those folks. So like, look, I, I think what you need is someone who finds space and, and wants to collaborate and wants to work and like we, we had a handful of sessions that, [00:03:00] I remember vividly where you brought me in and we had conversations like sometimes, folks, one of our little hacks that we did that I thought was a lot of fun, and we still do to this day is like sort of evening meetings, dinner meetings at the office. Yeah. We, we do some takeout, usually sushi. Yeah. We're in a conference room.

Todd Olson: We got whiteboard markers going and we're just like talking. Yeah. Brainstorming. Yeah. with, with, everyone's idea is, is good and equal. I think that worked.

Trisha Price: I remember that one session we had on our embedded guides, our embedded content feature. Yeah. And I remember just sitting there and like getting your feedback and getting your opinion and putting it up there.

Trisha Price: And it's not like you directed me, you can't do this or you have to do this, but I want your feedback. You know the product, you're the founder, you know the space better than anyone. So for us to be able to collaborate on it but not feel like it was directive, I think was critical for both of us. 

Todd Olson: Well, I hope it was [00:04:00] fun for me.

Trisha Price: Me too. 

Todd Olson: And I hope it was fun for everyone, I think it wasn't just you. You had, you had, you, you had I think a level beneath you and a level, but 

Trisha Price: Yeah. So yeah, they were all in the room. 

Todd Olson: Yeah. And I think, I think at the end of the day, I'm a builder and I like to build things and it brings me joy.

Todd Olson: And, and I think, I like to think I, I my happiest self in some role where I can still build. And I'm not just stuck in, everyone assumes I'm just, the CEO I'm stuck in a bunch of meetings with. I don't know, bankers and finance people or whatever, sometimes. And, and I have to do those things, that's part of my job as well.

Todd Olson: But I, I think that the building part, that's where the magic happens. Yeah. In companies and that like, so yeah, I think you need a relationship where people don't feel threatened. They feel like each person understands their space, their role, but, and look, and then it's having direct conversations like, Hey, this didn't work for me, or, Hey, I'd like this more.

Todd Olson: I think. Having a good enough relationship where you can be open and honest. Yeah. And direct with each other 

Trisha Price: Yeah for sure. 

Todd Olson: [00:05:00] 'Cause you're not gonna be, 

Trisha Price: It's not gonna be perfect every time. 

Todd Olson: No. You're gonna like we all move very quickly. Yeah. When you move quickly, sometimes you forget to do something.

Todd Olson: You unintentionally exclude someone. May not even be me, maybe someone else. And like, I think working through that, that's really, really important. 

Trisha Price: Yeah. Well, I appreciate it and um. It's just something people ask me all the time and it's hard to explain how to make relationships work and working relationships and trust, but I think it's something we did really well and hope that sharing that's helpful for, for everybody else.

Todd Olson:  Well the key is sushi at the office. 

Trisha Price: Sushi at the office 

Todd Olson: after hours. You know that, that. It fixes most relationships.

Trisha Price: Maybe, maybe a bottle of wine with a sushi, maybe. 

Todd Olson: Yeah, a little wine won't, won't hurt the creativity. 

Trisha Price: It doesn't. It doesn't. It doesn't. So, Todd, this is Hard Calls, so I'd love for you to share with us one of the Hard Calls you've had to make in your career that was, fairly career defining for you.

Todd Olson: Yeah. Look I [00:06:00] think, there are so many. I'm gonna go back to one pre-Pendo 'cause I think it was one of the like, the sort of like interesting hard calls I made. I was, so this is at Rally Software just prior to Pendo, this is maybe two to three years before I started Pendo. I was, I saw this opportunity to build this add-on product and, I was not the head of product there.

Todd Olson: I had no power, no control, no resources to do it. I was in product marketing and but I had this opportunity and I saw this product and actually some customer built some open source product using our APIs and it was like, wow, all of our customers could use this. I mean, I'm talking about product market fit.

Todd Olson: When you have a customer build an add-on to your product that uses your data, you're like, okay, I know I want that. So I convinced a bunch of people to hire some consultants to take this open source [00:07:00] product and start productizing it with customers, over the next three to six months that, that, outsource team grew and grew and grew into it was like honestly kind of a full fledge engineering team, to the point where finally the CFO kind of woke up and was like, what's going on? We have like, is this like some slush fund that you're like directing funds to? And, that ended up becoming, a portfolio management add-on to our agile project management solution, which, the company ultimately sold to Computer Associates, which was in that space.

Todd Olson: But it was, I think it was that not letting title, not letting role. I eventually took over product shortly thereafter, so then I actually had probably helped ability to move the whole, like move a bunch of engineering resources onto it. We, we pulled it in-house, but I think just not letting things get in your way.

Todd Olson: I think that's how you make hard calls and like having conviction around something. So, so yeah, I'd say that's [00:08:00] it. 

Trisha Price: I love that. I have often given product managers the advice when they ask me like, how do you get promoted? I'm like, well, if you work at a high growth company, you don't have to wait till there's a job opening or your boss leaves.

Trisha Price: It's, I've always said, go create a hill and go stand on it. And that's exactly what you did. You created a hill. 

Todd Olson: Yeah. And so many people, they get hung up on their title or their role or this and that, and like, man, just go do it. Build a business case. Yeah. And just go, go get after it. 

Trisha Price: Make it happen. 

Todd Olson: And, and I, I think, and look that I wasn't the CEO of the company.

Todd Olson: I, I think the, the reason I like that story is that plenty of people can say, well, now you can make hard calls because, blah, blah, blah. But I think anyone can make a hard call in the company. Yeah. So you just have to have some conviction. 

Trisha Price: And what you did and pulled off is hard, but I do think today with the tools at our disposal, especially with AI, doing what you did back then should be even easier for people.

Todd Olson: Yes. Yeah. [00:09:00] Well, yeah. Yeah. Well, now I, I could've like, had AI take this open source project and work on it a bunch. Right. 

Trisha Price: You wouldn't need all that. 

Todd Olson: Yeah. No, I, I think, well now it's a different world. And yeah. And then speaking of course of hard calls, I, I think we are in a world today, we're literally, every tech company is being faced with hard call, after hard call, after hard call.

Todd Olson: And, it's completely unique in dynamic times. And, and while I used an older example, pre Pendo, I could have very easily chosen a number of of examples that are like far more recent, like in the last few weeks or the last few months. Yeah, because I think now is a time where I am, being not forced is the wrong word,

Todd Olson: 'cause it means that it feels like something, something's pushing me to do it. I, but I feel conviction around the need to make harder calls. 

Trisha Price: Yeah. 

Trisha Price: And is a lot of that just because of market dynamics, is that because of AI in your belief in how software's changing? 

Todd Olson: Well, yeah. I, I think. You wanna [00:10:00] be capturing and jumping onto some of the most interesting waves.

Todd Olson: If you think about what sort of pulled Pendo along, you could argue sort of the SaaS wave when people were, yeah, building up software as a service and the whole cloud 100 community and like, like we sold to pretty much every one of those customers. And that, and the growth of those businesses fuel our growth.

Todd Olson: And that's kind of why we're sitting here in this nice office space. We grabbed onto that wave, but the next wave or current wave you could even argue is AI. And we need to find a way to lasso that and jump on it 'cause that is gonna fuel the next five maybe even 10 years of our growth. So, so the way I think of it is, is you want to be on the waves.

Todd Olson: It's gonna like the natural market forces to drive the next level of growth. But then it's also very, very clear that these tools are redefining the way you run businesses. Mm-hmm. And, and there's, it's, it, it's, it's changing the way we [00:11:00] develop software. It's changing the way we market to people.

Todd Olson: Yeah. It's changing the way we're gonna be selling to people. And because it's all very, very new, like there, the winners and leaders are gonna be ones that kind of figure out how to do it. Because the truth is there is no, like, people talk about, 

Trisha Price: There's no playbook right now for this. 

Todd Olson: Yeah. People talk about the SaaS, playbook's dead, you gotta do AI stuff, but they don't say that.

Trisha Price: There's no AI playbook!

Todd Olson: Yeah. And I, I speak with founders, both founders of AI companies who are younger than me. You could say they're AI native. Yep. Their age actually doesn't really matter. It it, what matters is they've been creating AI companies from start. And I, I talk with 'em to learn like, what are you doing?

Todd Olson: And I get some good nuggets and there's some obvi. We're all experimenting, but the truth is they're just experimenting like the rest of us. Yeah. And they have yet to figure it out. And because the truth is we just don't know. We just don't know what, what, how to do things the right way. How to use these solutions.

Todd Olson: And the tools are changing 

Trisha Price: Yeah. 

Todd Olson: Nearly every week. 

Trisha Price: Yeah. [00:12:00] 

Todd Olson: And so that makes it very exciting. A little bit scary, but as someone who's a, honestly a lifelong entrepreneur. Yeah. I've been starting company since I was 20. To me, I feel like the company needs me to be more entrepreneurial. Go back to sort of this day one mindset that Amazon talks about.

Todd Olson: I think that is what the company needs for me now, because the reality is that at nearly 900 employees, we have a lot of folks here slash leaders here who we hired because they're good at scaling big things.

Trisha Price: Mm-hmm. Which is not the same thing as going back to AI native and no rethinking how you, it's very different skill sets.

Trisha Price: Yeah. And, and you're at this interesting inflection. You actually need both. Correct. You need scale, you have enterprise customers, you have a pretty big company at this point. Yet at the same time, you've gotta kind of start over with how you think about your product, supporting customers, how you do business, like, how do you do both of those things at the same [00:13:00] time?

Todd Olson: Yeah. We can't be like, you know, cowboys running this company. We're a decent sized business. 

Trisha Price: Yeah. 

Todd Olson: And, and like we need professional HR practices and finance practices. We're audited by a big five accounting firm. We need these things obviously. Yet you kind of have to like be comfortable throwing certain things away.

Todd Olson: Yeah. And experimenting. And the question is, who at the company has experience such interest in going back to sort of day one. And, and the truth is, it's like I'm one of the few people who's very comfortable in that world. Yeah. So the company needs that out of me more and, and while I still do plenty of scale things, I mean, I'm, I've got like 12 hours of QBRs this week, or no tiny company would do.

Todd Olson: And maybe we won't do in five years, years, maybe not, I don't know. I honestly don't know. But I'm gonna do 'em the next two weeks. I don't, not because I think it's, I think it's a good practice. I like reflection, but yes, but yeah, I think it's, yeah, super [00:14:00] interesting and dynamic. 

Trisha Price: It is really interesting and I love what you're doing and challenging all of the status quo and processes and tools and the way we've done things.

Trisha Price: I think in product, when I talk to product managers, product leaders, I mean, the first thing I tell them is if you are not trying out all of these AI tools, if you're not prototyping, if you're not changing up your product development lifecycle. And I'm not even talking about putting AI in your product yet.

Trisha Price: I'm just talking about using it. I tell people all the time as a product manager, you are going to be completely lost and not have a job in a very short period of time because I think it is the most interesting time to be in product. But if you're not jumping on this wave and trying these new tools, you're just gonna be lost.

Todd Olson: No, a thousand percent. And, and I include myself in that world and that that was one of the things that it took me longer than I would've liked, but for a while, obviously as is happening, I go [00:15:00] to our leadership team, you at the time, others, we need to do more. We need to do more. Let's do this, let's do that.

Todd Olson: And we started doing things. I think we did our first AI hackathon like pretty early years ago. 

Trisha Price: Our AI launch was pretty early. 

Todd Olson: Years ago. Yeah. 

Todd Olson: Yeah. And that was sort of our, you, we can call it 1.0, we can call it 0.5. I don't know. I don't like naming things, but that was our first foray and just like touching, experimenting, and you could see some teams we had were just more natural early adopters of it, playing around with it.

Todd Olson: Right. And, we did, we did well, we got out there in the market. We started experimenting with customers, but I, I just felt very anxious the whole time we weren't doing enough. Now, I couldn't put my finger on what we needed to do. Right. And I couldn't say, put three teams on A, B, C 'cause I had no idea at a what, a what A, B, C really was at the time.

Todd Olson: But I knew in my heart, I just have, I felt anxious for the last few years. Yeah. Which is a weird feeling to have. And it's not constructive either, just me walking around being anxious. But I think what happened is about [00:16:00] nine-ish months ago, maybe longer, I really started personally playing around, like you just said, product managers should be playing around and using this.

Todd Olson: I started playing around with it a lot more. Yeah, I started experimenting, not just with Chat GPT, which everyone sort of experimented with, but I, I started experimenting with those, some of the prototyping tools, the prototyping tools and the code generations for zero and Lovable and things like that.

Todd Olson: And, and as someone who is a programmer professionally, and I don't get paid for it now, but I used to get paid for it, so, I was a bit skeptical at first of all this, but once I started using it, I was blown away. 

Trisha Price: It is 

Todd Olson: And yeah. Is it right all the time? No. And does it like generate code that has bugs?

Todd Olson: Yes. Yeah. But if you tell it, go fix it, it tries and does a decent job. And if you give it more direction and, and then the other thing is the models are getting better and better. So like maybe one week it generates sort of the wrong thing and then three weeks later it generates sort of the right thing.

Todd Olson: Yeah. I mean, you can kind of see where it's going and [00:17:00] you're like, wow. Wow. And I still felt it was valuable for me to have technical skills, but it was also valuable that I have product skills. And I have, I mean, I'm not a designer that, that, that's the interesting thing is a lot of us who are builders, we have majors and minors and look I cannot design things, period. So I'm just gonna say period. No one's ever put me in front of Figma. I've never used Photoshop in my life. I think I have a taste. I have things I like. 

Trisha Price: You have an eye for it. You have an eye for it.

Todd Olson: I appreciate certain things that are well designed. And my wife doesn't think so about furniture, but I think I have a decent taste, but certainly on software design, I think I have pretty good taste. But then of course, product, I would say is sort of a major of mine I've been doing now for years.

Todd Olson: I feel like I have a pretty good skill set there. And then of course, engineering and coding, [00:18:00] I have a good skill set, but I probably am rusty, not probably, let's just say I am rusty.

Trisha Price: Me too.

Todd Olson: AI sort of fills in those gaps. 

Trisha Price: It does. 

Todd Olson: And that, that's the power that I started seeing is like, it takes someone like me who is a major in something and but I have some weaknesses in other areas and it fills in those weaknesses.

Todd Olson: Yeah. And I get a lot done. Yeah. Now maybe it's not like production quality for like a Pendo, but it's a pretty darn good prototype that I could hand off to someone. And, and once, once I started playing around with it more and touching it more it really helped drive a lot more clarity about what we needed to do.

Todd Olson: And then others in the org started playing around with it more and that's when you realize just what's leadership about? It's about setting an example. 

Trisha Price: Mm-hmm. 

Todd Olson: And if I'm not playing around with it, which candidly

Trisha Price: I can't expect everyone else to

Todd Olson: Yeah. That, that really hit home. And look, I think the Shopify memo, which was earlier this year. Yeah. And some people didn't like it. Some people did like it. I had a chance to [00:19:00] hear, the president of Shopify, Harley, speak at a small event and they use this term reflexive and it resonates with me. 'Cause I don't know, I don't know about you, but like, I still reflexively use Google for a lot of things.

Todd Olson: Mm-hmm. I have a question? I Google it. 

Trisha Price: I've kind of switched over to ChatGPT. My kids make fun of me all the time. They're like, mom, that's something you could actually just Google, but I have kind of switched my reflex now is to go to ChatGBT.

Todd Olson: Well, I'm still working on it. I mean, I would say I'm 50/50 now.

Todd Olson: Yeah. But, but I'm not 80/20. And, and maybe there is a world where like, depending on your, your, your kids', point, like Google's gonna be better at certain things. 

Trisha Price: Certain things. That's what their point. They're like, if you don't need an opinion. Just go to Google. Yeah. You know? 

Todd Olson: Well, and when you go to Google now, it gives you an AI summary at the top, which is pretty darn close.

Todd Olson: It's pretty good. It's, which is pretty good. So like, like we're seeing these sort of like [00:20:00] different ways of working evolve and we're all experimenting their own personal hacks. But if we don't do it ourselves, like no one else, we can't expect our org to do it. 

Trisha Price: So, you've talked about leading the way for your AI revolution at the company, by playing with tools. You also went out and did a couple of exciting acquisitions in the AI space. Yeah. And so how do you think about that? Like how do you think about, obviously when you're talking about internal and ways to work, it's about tinkering and experimenting and playing, but when you're talking about changing your product, for all of us product folks, acquisition is a great way to do it.

Todd Olson: Yeah. Look, I, I think it was clear that we needed to inject some different experiences, different skill sets, different DNA, Yeah, in the business. When we, so the first acquisition we made in the AI space was Zelta AI, and that was the result of actually us being, I would say, [00:21:00] intentional in our MA strategy.

Todd Olson: Yeah. We went out looking for a product that sort of solved that problem and the problem was very, very specific and everyone in product knows it. We have lots of qualitative data. It's sort of like scattered across our org in these different systems, yes a PM could go and read through every 

Trisha Price: Call log and support tickets, 

Todd Olson: Yeah.

Todd Olson: Zendesk ticket and like, pull out the, 

Trisha Price: Enhancement requests 

Todd Olson: And no one does that. But it's super valuable. Yeah. And there's like gold in those hills. Yeah. I like to say. And if we can find a way to ingest it all and, and, and really surface those things that's incredibly valuable to customers.

Todd Olson: And so we kind of set out to sort of, be very intentional about acquiring it as, as and, and then it was super interesting 'cause as you meet companies and there, some of our investors guided us on this, that you actually [00:22:00] almost wanted younger companies. Yeah. Which may be counterintuitive because if you started too long ago, you were pre LLM and a lot of those companies were rewriting their stacks to leverage LLMs.

Trisha Price: Right. We wanted specifically the skill sets and the tech that was post. 

Todd Olson: Exactly. 

Trisha Price: LLMs 

Todd Olson: Because they're just building things in different ways 

Trisha Price: And that's the skillset we needed. Exactly. We didn't need people who were learning it. The same way we were learning and trying to pivot to it. We needed people who natively thought and built their products that way.

Todd Olson: Exactly. Yeah. And, and so that's what we did. And, and I think it's been successful on a number of fronts: One the product's great, we're excited about it. It's in market. I've gotten a lot of positive feedback from customers around it. Some CEO grabbed me the other week at a conference, told me how I was transforming their product practices.

Todd Olson: So that felt really, really good. But also like the DNA change, like, whether it's like the engineering team operates differently. A little more [00:23:00] agile, they've been using AI tools from day one. Yeah. One of the things I, I was seeing an engineering meeting with one of the engineers from, from Zelta in a bigger engineering room and it was all about how to use AI in engineering and a bunch of engineers were talking about.

Todd Olson: Well, it couldn't handle this tail recursion example that I had or whatever they, I think a number of folks were experimenting with things and like you passed some sophisticated algorithm and it got confused, et cetera, et cetera. And the engineer from Zelta, everyone's breaking it basically and can't use it for this. Can't use it for this, can't use it for this. And one thing that Mick said that really struck with me, he is like, look, I can spend two hours typing or 30 minutes reviewing. And it's just faster to spend 30 minutes reviewing code than it is two hours a type code. And it changed my mental model to like, [00:24:00] are a lot of us gonna start really honing our editorial skills? Yeah. Where we may not be generating large swaths of content, but we may be curating it. Yeah. We may be editing it. Yeah. And like, if you think about the world we're in now, like we love editors and curators that like, those are the people that are influencers across social media.

Todd Olson: Like the people that we all follow are essentially people pulling out the good bits and surfacing it to us 'cause that's what they think we should be looking at. And I think, so we've already, as a culture, started moving in this direction. Yeah, I think we're gonna. Yeah, large language models and generative AI

Todd Olson: It is gonna push us all to be a set of curators, editors and that's actually pretty exciting for me. 

Trisha Price: It is. So, it is, it's really exciting. And then you followed on from Zelta and did another AI acquisition as well, 

Todd Olson: Correct! Yeah. Yeah. And we've done two acquisitions in 12, well, three actually, [00:25:00] technically we acquired a small community called Product Collective.

Todd Olson: But yes, this is the most aggressive we've been in market, since we started the company. We've done, we averaged by one every two years prior to this. And now we're, we've done several in, in one year. And that was Forwrd.ai and that was another intentional purchase. We know that our data is super valuable for certain business outcomes, like detecting churn or expansion signals, which ultimately they on driving revenue, like scoring leads or product qualified leads, things like that.

Todd Olson: But it's a hard problem. Yeah, it's a hard problem. It not only do you have our raw data, which sort of needs to be cleansed and sort of massaged and you need to sort of, you know, join it with CRM data and other data, like it's a relatively hard challenge. And look, some teams, some companies have data science teams and they, four or five people, maybe half [00:26:00] dozen people that can sort of do all that work.

Trisha Price: I mean, we do, we do. We have been doing that on. 

Todd Olson: But that's a rarer skillset. Yeah. And that when I talk to our customers, even some of our larger enterprise customers, they aren't doing that. Yeah. And this is an opportunity to, to take our data and honestly drive revenue for our customers because when I talk to our customers, a lot of 'em kind of, they wanna do this, they're trying to do this; they have limited skill sets, limited, like the skill you need is like taking Pendo data and sort of making it relevant. 

Trisha Price: Right. 

Todd Olson: It's, and they just don't understand it to the degree.

Trisha Price: And the Pendo data is. Is nuanced to it's nuanced, get the right insights out, sophisticated. 

Todd Olson: It does need to be, it does depend on like how you set up your subscription in some instances. Yep. And we have all the expertise in that on that. But what we've seen is this, this, our data is a really, really good non-biased, early warning signal for 

Trisha Price: That's really cool.

Todd Olson: For all these opportunities. So yeah, that, that's been really, really exciting. And, um. [00:27:00] And it's just a great team. Another thing comes down to, I, I've talked to hopefully in both instances, yes, the product, we were intentional, the use case we liked, but the team's adding something else. Yeah. 

Trisha Price: And this entrepreneurial mindset, AI talent, different points of view of doing things.

Todd Olson: Yeah. I mean, Kobe, was a product leader in our space so, obviously bringing his background and experience to Pendo is, is super helpful, super, super helpful. Well, we already had a team in Israel, so like that in some ways that made it actually really, really easy. Yeah. Yeah. In an office, like literally it, it closed.

Todd Olson: Next day everyone's in an office doing a town hall, having lunch together. That's great. So, um. Yeah, 

Trisha Price: Culture's important with these things. So both of the acquisitions that you talked about, were really using AI to glean insights into your product. 

Todd Olson: Correct. 

Trisha Price: Into our product. Mm-hmm. But I know a lot of listeners, us too, when we think about [00:28:00] AI, we think about insights, but we also think about this whole agentic world and where automation of workflows is going. Conversational interfaces is going and that's something I know that, that you've been working on, not just for Pendo and our product, but also supporting everybody else, all the other product people out there as well, and building their agentic experiences.

Trisha Price: So how, how are you, how are you instilling those new skills and talents? Because that's a different skill set than gleaning the insights that you were talking about from Zelta and Forwrd. 

Todd Olson: Correct, correct. Well, the first thing before I move on from insights, I will say like the first thing we sort of prioritized and built, which, I feel really good about was it was clear as you're starting to, Hey, what do we do? At some level, we, we are measuring user interfaces and experiences. There's no question that the world's moving where we're gonna have, we're still gonna have clicks and scrolls and page loads [00:29:00] but some percentage of our user interfaces are gonna be agentic, chat-like in nature, whatever, whatever, copilot-ish - and there's just so many different terms - and I don't know if that percentage is gonna be, like, some people probably are theorizing, it's gonna be a hundred percent of user experiences. I'm probably not on that boat where it's gonna be a hundred percent.

Todd Olson: I think power users are gonna want different experiences. I know I, as a power user for software, like I just wanna,

Trisha Price: Somebody just wanna go do something. I know I can do it. 

Todd Olson: I just wanna go in and click a button or two. Like Right. I, yeah. I don't need to like, type in a sentence every time I wanna do anything.

Todd Olson: Right. So I personally don't think it'll be a hundred percent, but I think a lot of people are gonna try to do it and they're gonna experiment with it. So, but regardless of what it is. I know that people are gonna measure that part of their app, and if we see all these other stuff and we don't see this, then we're not providing a hundred percent visibility into how people are experiencing your product.

Todd Olson: So, so the first thing we, we sort of prioritize what we're calling agent [00:30:00] analytics, which leveraging the same Pendo install, the same Pendo infrastructure. You can basically direct us to say, Hey, take this agent. It starts pulling in the actual conversation, and start giving you insights into how people are doing it when they're doing it.

Todd Olson: How they're working in concert with the other parts of your product, start getting like honestly just 360 degree visibility of what's going on. So that was kinda step one. And that's powerful because as step two for us is okay, now we need to add sort of that user interface element to our product.

Todd Olson: Yeah. And that different way of experiencing the product and when we first started going down this path, honestly, I, we made an intentional decision to sort of let teams run their own experiments independently, we did not centralize it. Yeah. We didn't create one piece of infrastructure.

Todd Olson: There's just so many different types of infrastructure and so many different decisions, we [00:31:00] decided that picking one too early could lead us down a path where, pick the wrong one. Yeah. So like, let teams experiment, give people like creative license. And we did that and, we ended up with, three agents, four agents, whatever, you, whatever, I don't know what the exact number is, but a number of different agentic experiences in Pendo. Yeah. Now you're gonna start seeing us sort of like 

Trisha Price: Bring that together 

Todd Olson: Now that we we know enough to know what's working and what's not working, start creating some common infrastructure, common UI elements. We have an opinion now, almost a point of view like, so to taste, so to speak, and what we think the right experience is long term and that's the process we're sort of going through now. 

Trisha Price: So as product leaders, this is a conversation I have with other product leaders all the time.

Trisha Price: Which is not the technical challenge of doing what you're about to do, but the emotional and change management of it. Because you go [00:32:00] and you let your various teams and product teams build what they wanna build, and they all think theirs is the coolest and the best. And there probably are pieces of each one of them that are the coolest and the best.

Trisha Price: But then you come up with sort of a, a combined point of view of where you wanna go with one experience, and then everyone has to kill what they had built before. And there's like this real sense of loss 'cause the best product managers love what they built. They fall in love with it. Yep. And then you gotta tell 'em their baby's ugly.

Trisha Price: Or even if their baby's not ugly, it's not the prettiest. And so how are you dealing with that? In terms of, helping people still feel connected to the strategy and, and not feel that loss. 

Todd Olson: Yeah. Look, I think we treat all of these things as, this goes back to the, the very classic book of Lean Startup, but I, I see, I always say like, the value in, in, in all of this work, whether you throw it or not, is validated learnings. Yeah. [00:33:00] We have valid, we have a validated learning around, a, a certain path or a certain technology set maybe it doesn't scale the way we want. Maybe it doesn't quite hit our quality bar.

Todd Olson: Maybe it's hard to maintain. I, I think we're gonna have to take some risks and be comfortable throwing things away in this new environment. Yeah. Just like we did day one. Yeah. We're gonna make mistakes and, and technology's we're gonna wake up one day and we're like, oh wow, 05 just dropped and it's like freaking amazing, you know? And like, we need to move everything to that, you know? Yeah. Sorry, GPT5. Yeah I think it's just trying to get, reprogram people's mindset to be like, don't get too attached or married to anything. Yeah. And, but you also need to iterate very, very quickly.

Todd Olson: Yeah. Like if you threw away 18 months of work, that's different than throwing away six weeks of work. Right. So, so we're trying to move very, very quickly and continually evaluate it. 

Trisha Price: [00:34:00] Yeah. I think it's important for all product managers and product leaders always to think this way: quick experimentation.

Trisha Price: Don't get too tied up in something or your idea, you know? But right now with AI and how quickly things are moving and changing, and what technology is allowing us to do today that it didn't two weeks ago, not two years ago, two weeks ago, more than ever, I think we all have to be comfortable with that.

Todd Olson: Yeah. Well look, one of my classic expressions in product is don't get married to your roadmap. 

Trisha Price: Yep. 

Todd Olson: Another one of my classic expressions is it's not your roadmap. It's my roadmap,meaning it's the company's roadmap. Yeah, that's right. Just like it's not your budget, it's the company's budget.

Todd Olson: That's right. Like you are curating it, your managing it on behalf of the company. But if you think it's yours, you are candidly wrong. 

Trisha Price: No, we, we owe outcomes to our investors. Yeah. And we owe value to our customers. Yeah, that's it. It's, that's what the [00:35:00] roadmap is, 

Todd Olson: You knows, and if it's wrong, we will change it.

Todd Olson: Yeah. And I am completely unafraid. And, look, yeah. You have to deal with the, the constant, oh, everything's changing and we can't even like, stay in one thing long enough to like, you know. Okay, great. 

Trisha Price: Yeah. The world is changing right now. 

Todd Olson: The world's changing. I'm not changing it, you know?

Todd Olson: Yeah. But we're gonna, like, 

Trisha Price: We didn't invent GPT five, but we better take advantage of it. 

Todd Olson: Exactly. Like, if, if you're not comfortable sort of like adapting to the environment, you will miss out on things and I don't miss out on anything. Yeah. Like, like that's certainly not how we're gonna roll here.

Trisha Price: Yeah. Agree. So Todd, we've talked a lot today about AI and the impact to Pendo, both using AI to build our products and sell our products and everything, and then also agentic experiences and insights in the product. But we also have a lot of sophisticated enterprise customers who love AI [00:36:00] and are partnering with us on this AI journey, but they're still what I would call regular features and things that they need and expect from us.

Trisha Price: So how do you balance those things? How do you make sure you're taking care of your customers in the traditional sense, not just in terms of leading the charge with innovation and acquisitions? 

Todd Olson: Yeah. I mean, look, I think. The title of the podcast is Hard Calls. This is a hard call. Yeah. Like what, what do you spend on, various pieces, in various, parts of the roadmap.

Todd Olson: I, I think this is, this is why we all get paid the big bucks in product, is to make those, those decisions. And look, the, the truth is you're gonna have to invest in a lot of things for your enterprise customers, especially a company like Pendo, which is still sort of on its journey towards the enterprise.

Todd Olson: Yeah. Features like bulk operations. And look, I, I know that, some engineers or other, well, that's not the exciting features. It's exciting for large enterprises. It's, yeah, if it's, if you just [00:37:00] save them like 20 hours of work because you did something like in one click versus like them spending an hour or 20 hour, whatever it is.

Todd Olson: Like, like those are the features you need to do. I mean, but, but we often forget is that large enterprises, some of 'em are heavily software so that we, we protect them as they're sort of like going through their journeys.

Todd Olson: Now the cool thing is, is these two sort of pillars are coming together where, these large enterprises are, many of 'em are trying to experiment with AI. They want to experiment with AI. They may not be exactly ready for it this moment, but they're gonna want a partner like us who is already meeting their needs in other areas of their business to sort of help them along that journey.

Todd Olson: Yeah, and I think that's where we think the real opportunity is, is while we're now experimenting with it with maybe our more innovative customers are, are smaller customers, startups even are starting [00:38:00] to, to, leverage some of our AI solutions. We'll work out the kinks, we'll perfect them, we'll get them, in a really, uh, production quality sort of like position and then we'll be able to bring a lot of those to, to our enterprise customers. And I think it's gonna be a win-win for everyone. But, but yeah, you have to balance all these things. And it's gonna be interesting is that as enterprises adopt AI, they're gonna want more controls. 

Trisha Price: Yeah. 

Todd Olson: They want, 

Trisha Price: Specific permissions. We can use this, but we can't use this. We can use certain types of AI but we can't use other types of AI. 

Todd Olson: Exactly like they're gonna want potentially to use their own large language models that are possibly tuned for their own environment, 

Trisha Price: Self hosted. And yeah, 

Todd Olson: Yeah there's a lot of examples like that that are things that we would do for our large enterprise customers.

Todd Olson: Yeah. Like, there's really good reasons for those companies to require that, which still allow us to deliver a great product experience. So why? Like, [00:39:00] I don't necessarily, I'm not super concerned. Now, that's not ever like a version 1.0 feature you're gonna build, but yeah, I think you have to pay attention to both needs and you have to invest heavily in both and yeah, we, we have a lot of customers. If I showed up at our Pendomonium. which is our user conference and said, we're only building AI features. 

Trisha Price: People get upset. 

Todd Olson: Yeah. They get upset and rightly so. Yeah. I don't think it's the right decision. Yeah. But we're gonna invest a lot in AI because I think it will, the enterprises will want it.

Todd Olson: Yeah. We're already seeing, like some of our large enterprise customers ask us for things, I mean, agent analytics is a great example where we have some large enterprise customers that are starting to experiment with it and use it and because they have mandates to play around with AI and they just wanna know, are these things working?

Todd Olson: Yeah. What is it, 

Trisha Price: What are people doing with it? What are they trying to solve? How are they using it? Who's using it? 

Todd Olson: Exactly. And, and, and because when I talk to some of large [00:40:00] enterprises, they're not seeing necessarily the the the benefits yet? Yeah. That they're reading about in the news, so they're hoping by better understanding it, understanding how people are using it, they can tweak and tune and ultimately get those, those outcomes. So, so yeah, I think it's a constant balancing act and we'll see. We'll see how it goes. 

Trisha Price: Great. Well, Todd, thank you for being on Hard Calls today. This is obviously a fun episode for me to record, and just really appreciate you sharing your experience with us in terms of Pendo and really fun to be here, live in Raleigh.

Todd Olson: Well, it's fun for me too, so thank you. 

Trisha Price: Thank you. Thank you for listening to Hard Calls, the Product podcast, where we share best practices and all the things you need to succeed. If you enjoyed the show today, share with your friends and come back for more.