Damian Olthoff Is Ready for What’s Next

Damian Olthoff helps PROS expand by investing in forward-thinking initiatives and getting into the weeds of the tech that can augment the success of his team and customers

Midwestern roots still run deep in Damian Olthoff. The nine-year general counsel at cloud-based software company PROS is quick to laugh. And despite his company’s being responsible for the real-time intelligence and analytics that power more than two billion airline tickets sold per year flow seamlessly, Olthoff still regards himself as a relative digital dilettante whose early interest in coding hasn’t kept up with the digital revolution of the past few decades.

But it’s when he talks about what his PROS legal team has offered the rest of its organization—not just in counsel, but in digital initiatives to make an already tech-centered company even more agile—that one gets the sense Olthoff is downplaying his own abilities. The GC’s inherent interest in the future of artificial intelligence (AI) and machine learning puts him in a league of his own when it comes to future-forward general counsel, and PROS is all the better for it.

Damian Olthoff, General Counsel and Secretary, PROS Photo by Michael Reiland

The Best of Both Worlds

“I tend to think about solving problems in legal transactions and engineering very similarly,” Olthoff says. “Whereas engineers are using math and science, we’re using precedent, history, and logic. But it’s not until you get all of the components and parts working together that you’re actually able to make something, whether that’s a bridge or a contract.” The future GC helped put himself through law school by coding websites for law firms who were looking to establish a digital presence in the early internet boom.

A confessed “history and tech geek,” Olthoff has earned a deserved reputation as a lawyer who tends to get down into the weeds of the technology that helps enable the success of both his company and his customers.

“I’ve realized in talking with other general counsel that they’re not often thinking at the level of detail that I may very quickly go to,” Olthoff says, laughing. “I don’t need all of the explanations and buzzwords. I’ve got most of that coming into the conversation. That gives me a bit of an advantage just in terms of being able to understand the situation. If someone doesn’t understand the difference between source code and object code, they’re going to have a much steeper learning curve as a result.” Olthoff says this all with a Kansas City–born humility that almost makes it sound like he’s apologizing.

According to Tony Campiti, who serves on the management committee of Thompson & Knight and has worked with Damian throughout his career, “Damian’s Midwestern friendliness and humility are sincere,” Campiti adds, “He’s the quickest study you’ll ever meet, and his keen analytical curiosities, entrepreneurial bent, and yearning to grow make him the perfect legal advisor for PROS’s ever-evolving business.”

The Fourth Phase

In nine years with Houston-based PROS, Olthoff says the transformation of the company has been staggering. “I feel like I’ve worked for four different companies, and I know others on the senior management team will tell you the same,” the GC says. “When I joined, we were a US-only, on-premise software company with fewer than three hundred employees. Now we’re all over the globe and cloud based, with more than 1,200 people.”

Olthoff credits CEO Andres D. Reiner for the revolutionary change and growth he’s seen and been part of during his near decade. “He really helped move us into a phase of thinking about growth, expanding the products we sold, and where we would sell them,” Olthoff says.

During Olthoff’s tenure, the company has opened offices in Germany, France, the UK, Bulgaria, and Australia, among other places. The transition from on-premise to cloud-based work meant an entirely different operating model.

And then came what Olthoff refers to as his “fourth phase”: the challenges and evolution needed to accommodate constantly changing privacy expectations and building for scale. “And that’s where we are right now,” Olthoff says. “We have all of these great assets and an unbelievable team. We’re looking ahead.”


Olthoff is obviously passionate about his employer, and it’s easy to see what has kept him for a length of time other lawyers may have been in three or four different jobs. “This is literally the highest-IQ group of people I’ve ever been around in my life, but what makes it so unique is there is no ego here,” Olthoff says. “We’ve had customers describe to us that when they go into a meeting, they can’t tell what department we work in because everybody is just working together to solve whatever issue that’s there.”

PROS has assembled a heavy-hitting team while ensuring it is steeped in diversity. GC says that isn’t just a PR move; it’s in the PROS DNA. “I know it’s big in the news right now, but we have valued diversity all the way back to the founding of the company. The sheer number of languages that are spoken in our offices is incredible. We have the best and the brightest here from all these different disciplines and cultures.”

That has Olthoff excited about the future. He is particularly interested in how PROS can use AI and machine learning to cut down on repetitive tasks so that employees might focus more time on higher-level work.

“One of the smaller things we’ve done is to use technology to cut down on the amount of time and effort it takes to get an NDA [nondisclosure agreement] signed,” Olthoff says. “It’s such a small piece, but any attorney that has ever touched an NDA would appreciate it immediately.”

But the GC is thinking bigger. “Lots of us, myself included, have had these big amounts of data: what’s in market, what’s out of market, trends in your team’s performance, macro trends over time. But if you develop a system that is able to run these numbers and tell you, statistically and in real time, where you should be, there’s so much less time you’ll spend looking over your back.

“To be able to develop a system that configures to your specific customer gets very interesting,” he continues. “For example, I’m confident that in ten to fifteen years, you’re going to see a world where businesses are going to start coming together to offer things that are interdependent and seamless through your phone.”

Given PROS’s massive influx and continued growth, it’s easy to see why Olthoff might still be there in a dozen or so years, in yet another phase, always on the edge of what’s next.

Comfort from the Storm

Part of Damian Olthoff’s passion for PROS is the family-like attitudes he sees reflected in his executive team. During Hurricane Harvey’s brutal destruction of areas of Texas and Louisiana in 2017, Olthoff saw the true heart of PROS on display.

“I don’t want to embarrass them, but we literally had senior leaders getting in their personal cars to go rescue people who worked here, though they didn’t know them personally,” Olthoff says. “They just did it because they had the ability to.” The company also booked hotels so that displaced employees had a place to stay, covering deductibles for those who needed it.