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. 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 Olsen.
Hi Todd.
Hey Trisha. How you doing?
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. 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.
Sounds good. Sounds good.
So, for all of you guys, I was hired as the CPO here at Pendo about four years ago. Todd hired me in. And I often get the question, 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 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 works.
Well, first off, I think very few things intimidate you. So, you need to find someone who comes from, you know, is cut from that cloth that you obviously if I'm speaking to someone and they're intimidated by me, it's just going to be a bad relationship from the start. I mean, I don't think any relationship in life is positive where one person is intimidated or has issues with the other person, especially not a leadership position. But look, I think you want and I think you did this well is you want to find someone who wants to partner with you.
Yeah. Who doesn't try to box you out, shut you out, rather finds a way in a very healthy way to sort of make room for you within the org. I mean, you know, the reality is running an org at scale, there's a lot of things I probably don't want to do. Like a lot of things I don't want to do, a lot of things I didn't do.
Career frameworks and ladders.
Career, but even like the details of execution around a lot of which teams specifically like no one wants me in that sausage making and I don't 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 think what you need is someone who finds space and wants to collaborate and wants to work and like we had a handful of sessions that I remember vividly where you brought me in and we had conversations like sometimes 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, you know, we do some takeout usually sushi. We're in a conference room. We got whiteboard markers going and we're just like talking, brainstorming, you know, with everyone's idea is good and equal. I think that worked.
I remember that one session we had on our embedded guides, our embedded content feature. And I remember just sitting there and getting your feedback and getting your opinion and putting it up there. 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.
Well, I hope it was fun for me.
And I hope it was fun for everyone. I think it wasn't just you. You had a level beneath you and a love, you know. So yeah. And I think at the end of the day I'm a builder and I like to build things and it brings me joy and I think I'm my happiest self in some role where I can still build and I'm not just stuck in everyone assumes I'm just as a CEO I'm stuck in a bunch of meetings with I don't know bankers and finance people or whatever you know and I have to do those things that's part of my job as well but I think that the building part that's where the magic happens in companies and so yeah, I think you need a relationship where people don't feel threatened. They feel like each person understands their space, their role, and then it's having direct conversations like, 'Hey, this didn't work for me or hey, I like this more.' I think having a good enough relationship where you can be open and honest and direct with each other.
For sure.
Because you're not going to be perfect every time.
It's not going to be perfect every time.
No, you're going to like yeah. Like look, like we all move very quickly. When you move quickly, sometimes you forget to do something or you unintentionally exclude someone, may not even be me, maybe someone else. And like I think working through that, that's really really important.
Yeah. Well, I appreciate it. And 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 everybody else.
The key is sushi at the office. 24 hours, you know, that fixes most relationships.
Maybe maybe a bottle of wine with a sushi. Maybe.
A little wine won't hurt the creativity.
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, you know, fairly career defining for you.
Yeah. Look, I think there are so many. I'm going to go back to one pre-Pendo because I think it was one of the sort of interesting hard calls I made. I was at Rally Software just prior to Pendo. You know, this is maybe two to three years before I started Pendo. I saw this opportunity to build this add-on product and I was not the head of product there. I had no power, no control, no resources to do it. I was in product marketing 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 talk about product market fit. 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 product to start productizing it with customers. Over the next 3 to 6 months that outsourced team grew and grew and grew into it was like honestly kind of a full-fledged engineering team. To the point where finally the CFO kind of woke up and like what's going on? We have like is this like some slush fund that you're 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 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 the ability to move the whole I moved a bunch of engineering resources on to we pulled it in house but I think just not letting things get in your way.
I think that's how you make hard calls and like having conviction around something. So yeah, I'd say that's it.
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. 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.
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 and just go get after it. And I think and look that I wasn't the CEO of the company. I was I think the reason I like that story is that plenty of people can say, 'Well, now you can make hard calls because, you know, blah, blah, blah.' But I think anyone can make a hard call in the company. So, you just have to have some conviction. 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.
Yes. Yeah. Well, yeah. Well, now I could have like had AI take this open source project and work on it.
Yeah. Yeah. No, I think well, now it's a different world. And yeah. And then speaking of course of hard calls, I think we're in a world today where literally every tech company is being faced with hard call after hard call after hard call. And it's completely unique and dynamic times. And while I used an older example pre-Pendo, I could have very easily chosen a number of examples that are like far more recent like in the last few weeks or the last few months because I think now is a time where I am being not forced is the wrong word because it feels like something's pushing me to do it but I feel a conviction around the need to make harder calls.
And is a lot of that just because of market dynamics? Is that because of AI and your belief in how software is changing?
Well, yeah. I think you want to be capturing and jumping on to some of the most interesting waves. If you think about what sort of pulled Pendo along, you could argue sort of the SaaS wave when people were building up software as a service and the whole Cloud 100 community and like we sold to pretty much every one of those customers and that and the growth of those businesses fueled our growth 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 because that is going to fuel the next five maybe even 10 years of our growth. So, the way I think of it is you want to be on the waves that's going to 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.
And it's changing the way we develop software. It's changing the way we market to people.
It's changing the way we're going to be selling to people. And because it's all very very new. Like the winners and losers are going to be ones that kind of figure out how to do it because the truth is there is no like people talk about no playbook right now for this.
Yeah. People talk about the SaaS playbook's dead. You got to do AI stuff, but they don't say what's in the playbook.
Yeah. And I speak with founders, both founders of AI companies who are younger than me. You could say they're AI native. Their age actually doesn't really matter. What matters is they've been creating AI companies from start.
And I talk with them to learn like what are you doing? And I get some good nuggets and there's some obvious we're all experimenting. But the truth is they're just experimenting like the rest of us and they have yet to figure it out. And because the truth is we just don't know. We just don't know how to do things the right way, how to use these solutions and the tools are changing.
And so that makes it very exciting, a little bit scary, but as someone who's a lifelong entrepreneur, I've been starting companies 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. I think that is what the company needs from me now because you know 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.
Which is not the same thing as going back to AI native and rethinking how very different skill sets and you're at this interesting inflection you actually need both you need scale you have enterprise customers you have a pretty big company at this point yet at the same time you've got to 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 time.
Yeah, we can't be like cowboys running this company we're a decent sized business, you know, and like we need professional HR practices and finance practices. We're audited by a big five accounting firm, you know, we need these things obviously, yet you kind of have to like be comfortable throwing certain things away and experimenting. And the question is who at the company has experience less interest in going back to sort of day one? And the truth is it's like I'm one of the few people who's very comfortable in that world.
So the company needs that out of me more. And while I still do plenty of scale things, I mean I've got like 12 hours of QBRs this week where no tiny company would do.
And maybe we won't do in five years. I don't know. I honestly don't know. But I'm going to do them the next two weeks because I think it's a good practice. I like reflection. But yeah, I think it's super interesting and dynamic. 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. I think in product, you know, when I talk to product managers, product leaders, I mean, the first thing I tell them is if you are not trying out all these AI tools, if you're not prototyping, if you're not changing up your product development life cycle, and I'm not even talking about putting AI in your product yet. 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 going to be lost.
No, a thousand percent. And I include myself in that world. And that's one of the things that it took me longer than I would have liked, but you know, for a while obviously it's happening. I go 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 and we started doing things you know I think we did our first AI hackathon like pretty early years ago.
Our AI launch was pretty early years ago.
Yeah, and that was sort of our you we can call it 1.0 zero. We can call it 0.5. I don't know. I don't like the naming things, but that was our first foray into just like touching, experimenting, and you can see some teams we had were just more natural early adopters of it, playing around with it. And we did well. We got out there in the market, we started experimenting with customers, but 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 and I couldn't say put three teams on ABC because I had no idea what ABC really was at the time. But I knew in my heart I just I felt anxious for the last few years, 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 nineish months ago, maybe longer, I really started personally playing around. Like you just said, product managers should be playing around and using this. I started playing around with it a lot more and I started experimenting not just with ChatGPT which everyone sort of experimented with but I started experimenting with some of the prototyping tools like Zero and Lovable and things like that and you know as someone who is a programmer professionally I 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.
It is. And yeah, is it right all the time? No. And does it like generate code that has bugs? 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 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 3 weeks later it generates sort of the right thing. You know, I mean you can kind of see where it's going and you're like 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'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 going to say period. So like 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. You have an eye for it. I appreciate certain things that are well-designed. 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 it now for years. I feel like I have a pretty good skill set there. And then of course you know engineering and coding I have a good skill set but I probably am rusty. Not probably. Let's just say I am rusty.
AI sort of fills in those gaps.
And 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. I get a lot done.
Yeah. Now, maybe it's not like production quality for like a Pendo, but it's pretty darn good prototype I could hand off to someone. And 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. And then others in New York started playing around with it more. That's when you realize just what's leadership about? It's about setting an example.
