If You Can’t Join ‘Em, Beat ‘Em: How Rob Butler Built Maestro Health his Way

Rob Butler wanted to be a baseball player. He played in college and then semi-professionally, but didn’t quite make it to the big leagues. He did, however, make it to the big leagues of entrepreneurship – having built and sold Payflex and MBI before starting Maestro Health in 2014. Rob was at MATTER recently for an interview with MATTER CEO Steven Collens as part of our Tales from the Trenches series, produced together with ContextMedia and Pritzker Group Venture Capital. Watch the full interview or read our recap below.

Maestro Health is reinventing how employees search for, apply to, and enroll in their employer-sponsored benefits. With more than 350 employees, $35 million in revenue, and $65 million in venture financing, Maestro is positioned to reinvent the employee benefits experience. But the most defining aspect of the company is clearly its culture.

Working at Maestro is anything but boring. Butler drew the company name from a Seinfeld joke, and on employees’ birthdays he favors in-office mariachi bands.

“One of our core values is fun,” said Rob. He believes that a fun workplace keeps employees happier and more productive.

“One of our core values is fun”

Butler hated his experiences in traditional corporate environments, and set out to build Maestro in the opposite vein. He felt that too much emphasis is put on the amount of “facetime” employees show at traditional corporations, and not enough on the quality or quantity of their output.

“Staying in the office until 9 pm? That’s just BS,” Butler said. “I decided that if I ever run a company, I’d make sure people go home to their families.”

This culture has helped the company weather conflicting egos, which often sink startups in their infancy.

“If someone tells you they don’t have an ego, they’re lying,” Butler said. “We all have egos, we just check them at the door.” And when people don’t, Butler is quick to move on. He’s let go of employees whose lack of integrity and self-control outweighed their obvious talents. “Words on the wall are just words, after all,” he mused. “But how do you act when things go wrong?”

“If someone tells you they don’t have an ego, they’re lying,”

Butler carries the no-frills, tell-it-like-it-is attitude he displayed at MATTER to Maestro’s external operations as well. When selling Maestro’s solution to a new employer, he doesn’t focus on what Maestro will do right.

“No no no,” Butler smirked. “We tell employers what we’re going to do when we screw up. Then we over-service them.”

In this way, Butler makes sure employers never leave Maestro, likening his company’s hold on its customers to “grimy in-laws.”

Butler is doing something right, with 500 organizations already using Maestro to manage their employees’ benefits, including Blue Cross Blue Shield of Arizona, Mazda, and the University of Texas. But he isn’t resting on his laurels. “We’re going to grow 50% this year,” said Rob.

No matter what’s in store for Maestro’s future, with Rob Butler at the helm, we know it won’t be boring.

For more on Maestro Health, visit their website. For more on Rob Butler, visit his LinkedIn.