Pendo CEO Todd Olson Discusses The Unicorn Turning 10 Years Old

Pendo CEO and Co-Founder Todd Olson presenting at the 2023 Pendomonium event last week in Raleigh. (Credit: Scott Roeder Photography)

Oh, how time flies when you’re having fun. And that’s exactly what Pendo has been having, as the Raleigh-grown unicorn celebrates its 10th birthday this month—its TEN-do birthday, if you will.

Since its launch in 2013, Pendo has grown to be one of the most valuable startups in the state and across the Southeast, with a valuation of around $2.6 billion (as of 2021). Pendo has grown from 35 customers for its early product platform to over 600 million monthly end users in over 10,000 companies. What once was a team of 12 has amassed over 750 employees in eight offices worldwide, including in London and Israel. 

Some other markers of Pendo’s rapid and consistent growth include opening a new five-story HQ in downtown Raleigh in early 2022, launching a plethora of new products and product suites that align with current and growing tech trends, and hosting seven annual festivals (the catchily named “Pendomonium“) that have expanded each year, capped by this year’s event held last week that included a performance by rapper Big Boi of Outkast fame. 

In celebration of its first decade in the books, Pendo CEO and Co-Founder Todd Olson spoke with GrepBeat. (Note: This interview has been lightly edited for length and clarity.)

GrepBeat: You just wrapped up the seventh iteration of Pendomonium, which amassed over 1,000 attendees this year. I’m curious as to why, seven years ago, you wanted to launch a conference only three years into business.

Todd Olson: There’s a tweet from Jason Lemkin, the founder of SaaStr, that says “once you have 100 customers, you have enough people to have a user conference.” When I first saw that tweet in 2016, it resonated with me. It’s an opportunity to foster a community and a sense of belonging. Customers are passionate about our product. They form a sort of relationship with our company because what we do is new for them. I think having a place where they can meet other people who are like-minded and share tips, tricks and ideas is just really successful for building a community that supports the company. 

Pendo’s pink dinosaur at its HQ in downtown Raleigh

GB: The first Pendomonium started with 150 attendees and now it’s over 1,000. How does that growth feel? 

TO: It feels awesome. And I want to double it, I want to keep growing it. Anyone who knows me knows that I want more, everything should and will be bigger. I have a lot of confidence now but from the very first [Pendomonium] to now, I am always shocked and surprised. Every year, I learn so much more about how people are using our products coming into the event. While we think we know what’s going on with our customers, we just learn so much more. 

GB: What, in your opinion, has been the biggest growth that you’ve seen Pendo amass over the last decade? 

TO: I think the biggest change we’ve seen is this growth in enterprise, this ability to work with these large traditional businesses, banks, healthcare companies, a lot of retail now. The types of companies we work with are really different now than they were before and part of that is what we’re working on in terms of applications that are employee-facing, like inside of retail stores or doctors’ offices. That’s the kind of growth and change that is super-interesting and what I feel has a lot of future growth for the company.

We have such a big opportunity here because a lot of people think of us supporting and driving customer-facing experiences. If someone comes into a retail store and they log into a system that’s kind of hard to use, it affects not only them but also the customer. It didn’t dawn on me until more recently. A lot of these retail employees are hourly workers so if they’re struggling to use software, that’s dollars out of the retailers’ pockets. If we can streamline any of that, that’s a lot of cost savings and, ultimately, leads to a better customer experience.

GB: Was this high growth something you expected from Pendo when you first started out?

TO: I think we certainly came out of the gate really fast, which was awesome. And we’ve maintained high growth for the last 10 years. It’s natural that growth slows down a little bit, but I’ll be honest, we keep fighting to grow faster. I wake up every day and I think about ways in which we can grow faster. It motivates me, gives me energy. I think [growth] is a big part of how we think and how we operate the business and we’re constantly fighting for more, not just standing still, waiting for things to happen.

One of the biggest areas of opportunity for us now is international growth. The biggest thing I’m thinking about for next year is how do we get overseas and how do we take and package what we have here. It’s kind of magical to be able to bring something to other countries, which will take a lot of adjustments and investment over time, but that’s what I’m focusing on now. 

GB: As CEO and Co-Founder, how does it feel for you personally to see this company grow not just in terms of product, but also in terms of people?

Todd Olson, Pendo CEO

TO: It’s almost immeasurable, the amount of change. You have to change as a company or it’s going to be held back. I can’t directly operate a company of 700 people yet I still need to maintain some of that entrepreneurial aggressiveness and risk-taking ability that we had even when we started with 12 people. It’s a balancing act between both but I’m very fortunate to have coaches that work with the company. I have a personal coach and a group of CEOs I meet with regularly, advisors, board members—I am surrounded by amazing humans that give me feedback and help me grow and I’ve had this support network for years.

I think every so often, you kind of have to reinvent your leadership style and adjust the way you’re working, especially alongside a growing economy. It’s different now than it was 10 years ago or even a year ago, so we will continue tweaking to see what is best for the company. 

GB: Do you recognize any growth in yourself just as a leader and a person?

TO: The job is definitely bigger. I’m treated a certain way because that job is a certain way, but I’m still the same person. I still and will always care about and work toward the same things. 

GB: How did you guys celebrate your 10th?

TO: In the office, we had a champagne toast and shared some celebratory stories. At Pendomonium, we had T-shirts that commemorated our 10 years. We definitely like our swag. But, one of the nice things we did this whole month is that we had images from throughout our 10-year history that would pop up on screens throughout the office. This was something very meaningful, it feels good to look at some old images from 2014/2015 to remind us where we came from and how far we’ve come. 

About Kaitlyn Dang 50 Articles
Kaitlyn is a reporter covering tech startups and entrepreneurs. Before starting at GrepBeat, she graduated from UNC-Chapel Hill with a degree in media and journalism in May 2023. She has written for The Daily Tar Heel. In her spare time, she likes going to concerts and going on nature walks.