Exclusive Q&A part three: Pendo’s CEO talks being the father of five, the color pink and the future

RALEIGH — After years of explosive “100 percent” growth year on year, cloud tech company Pendo is on the brink of reaching “unicorn” status. Its CEO and founder, Todd Olson, recently sat down with WRAL TechWire’s Chantal Allam for a one-on-one to talk about his whirlwind journey leading his startup to the top. Here’s the third of a three-part interview.

Let’s switch gears a little. Are you married? Do you have a family?

I have five children ranging from four months to 23. I have a 23-year-old son getting married tomorrow (June 1). Then I have 13 and 11 year-old daughters. Then I have a two-year-old son and a four-month-old daughter.

So how old were you when you first became a father?

So, we’re a modern family. When I married my previous wife, she had a six-year-old son, so he’s the one getting married. So he was six at the time and 23 now, so do the math on that. Then Eva was born 13 years ago, so I was 30. Then I married my current wife about five years ago, and had my son Anders [who is two] and [then our four-month-old].

How have you been able to grow a startup and have five children at the same time? How have you been able to handle this all?

There are good weeks and bad weeks. I do travel a lot more than I used to. That’s probably the biggest challenge – the travel. One, I do have a supportive spouse. That helps a ton. Without her, I wouldn’t have had the level of success and maintained the family life that I have.

What does your wife do for a living?

She’s an agile coach/scrum master/facilitator. She’s very organized, and that helps. And she’s in the tech field so I think she has more empathy for the role and understands it. She’s on maternity leave now, so it’s been even more helpful.

So do you travel a lot? How do you handle being away from home for long stretches?

Yes, but when I travel, I always take the red-eye flight to get home. That’s been one of my modes. I never stay the weekend. If I have the choice between taking a red-eye and getting home, or leaving the next morning, I always take the red-eye. I’m pretty tough on my body during the work week, but I’m always home on the weekends.

One of the other fun cultural differences about Pendo than other companies is that I do a lot of business meetings from home. I’ll invite people to my house when they’re out of town. We have out-of-town guests all the time, obviously visiting from different offices. If I could cook – actually now I’ve been catering – but I used to cook the meals. I’m gone about two weeks a month on average, and I try to be home about two weeks a month. You just try to find that balance.

If I’m in Raleigh, I try to leave by 5.30pm. It’s tough. Things like kids sports that occur at 4pm, it’s very difficult for me to get to that. I try once in a while to schedule that into my cadence, and I work later into the evenings, but I think you have to work on integrating work and life. We just had a sales club trip. It’s a work event generally for me. There is an expectation that I go. Although it is in the Bahamas, and it’s kind of a fun event, we brought all four kids. We made it a family- friendly event because I wanted to spend time with my family because I don’t see them a lot.

Those are some of the kinds of things that we built into the culture that I think has allowed me to do it.

Do you think the expectations on men and fathers these days are significantly different to generations before?

There are times when I feel like I’m not working enough, and times when I feel like I’m not being a father enough. Literally every day. I used to stress about it even more. Am I going to be the father that coaches the baseball team? No. At least, not doing this job that I’m doing now. But are there other benefits to my job? I’ve got hundreds of thousands of frequent flier miles and I can fly my family to different places. I took several of the kids to London when we opened the London office. My wife was on maternity leave, so she came with me. That’s an experience that you probably wouldn’t get.

We do obviously have help around the house. We have a full-time nanny. We probably couldn’t survive without it.

So does that understanding trickle down? Does it make you a more understanding boss?

Of course. People have lives. I know if you’re stressed at home, you’re going to bring that stress to work. Sometimes, if I even see someone stressed at work, I may ask, “Is something going on at home that we just don’t see?” And very often, it is. Having empathy for people and their lives is super important. I mean, we need to get things done. There is an expectation that we are going to get things done. I’m pretty tough on myself. If I need to get something done or be somewhere, I will do it. There is no question around it. Yes, but I think there is more understanding.

Finally, when you started this company, did you ever imagine you’d get to this point?

I wanted to win, and I wanted to go for it. There is no question about it. From the day we started this company, I wasn’t seeking some quick exit. I wanted to create a huge company. I don’t think I knew what that meant at the time, so I don’t think I anticipated all this. And I’ve been at bigger companies. But creating it yourself from scratch does feel a little bit different. It’s a little overwhelming at times. But yes, we’ve always been going for it.

It’s funny. Becoming a unicorn was never a goal, but the whole moniker was really popularized when Pendo started in 2013. I saw it, and I thought about it. I kind of set the goal then to get to $100 million in revenue. It felt like a better goal, and with typical public market multiples, $100 million would make you worth over $1 billion. Revenue was the goal. For a while, you couldn’t see it but it’s pretty neat that we can see it now. We’ll get to it. Now it’s not a question of if, but when. And when isn’t that far away. That’s kind of crazy to think it went from being zero to that much. Now I’m sort of thinking, what’s that next goal? Is $1 billion in revenue the next goal? Maybe.

What’s with the pink?

When I started the company, I knew I didn’t want to have a boring enterprise brand. Blue is supposed to be the typical enterprise color, and safe from IBM days. So I wanted to have something fun and I like pink, so I said let’s have a splash of pink. The original logo had pink as the accent color. Then at the first trade show that we went to, we didn’t buy a booth and we were trying to stand out. I was a bit inspired by a local company called Windsor Circle that wore these green pants. I was like, “Huh, why don’t we wear these pink t-shirts so we stand out.” It worked. Everyone knew who we were, and that was a time when we were tiny — a five, six person company. We went to do a rebranding at some point, and we put forth three designs and one was called “Bold Pink” and it was a solid pink website, literally pink bleed at the edges. We put it in front of customers and they fell in love with the bold pink. It reflected our edginess, our boldness. We were a different kind of company and all our customers felt it early on and they loved it. So we went with it.