Former Crew Services Supervisor earned his Endeavor pilot wings

Bo Rieger always dreamed of taking to the skies—but he never imagined his aviation journey would take off long before he ever stepped into the CRJ flight deck. Before earning his wings at Endeavor Air, Bo built a thriving career behind the scenes in Crew Services, discovering a deeper passion for aviation than he ever expected.

What followed for the former crew services supervisor, now Endeavor pilot, is a career fueled by curiosity, inspired by mentors, and shaped by the unexpected opportunities that aviation tends to deliver.

Back in 2018, Bo joined the Operations Control Center (OCC) as a crew services coordinator—originally just a way to fund flight training and get closer to the industry he loved. Instead, the OCC became his classroom, expanding his understanding of airline operations and igniting a drive to pursue aviation from an entirely new angle.

“I was still learning the job, and IROPs were always a challenge,” he recalls. “But watching the puzzle come together ignited my interest in the airline industry.”

Jump seat flights, base visits, and daily interactions with duty pilots broadened his view of aviation. Sitting alongside other OCC employees became some of the most formative experiences of his early career.

“They became mentors—whether they liked it or not,” he laughs. “Those moments made me a better aviator long before I ever stepped into the cockpit.”

Now wearing three gold stripes and a black blazer, Bo says he wouldn’t trade this career path for anything. Flying is the dream—and he’s living it.

He completed his private, instrument, and commercial at Flying Cloud in Eden Prairie, Minn. and earned his multi-engine rating at Aloft Aviation in Lakeville, MN.

His OCC background gives him a unique advantage on the flight deck, especially during ground delay programs (GDPs) and flow control.

“Pilots want all the information. If I didn’t know how GDPs worked, I’d probably be frustrated too,” he says. “My colleagues appreciate seeing what goes behind each decision from the OCC to the aircraft at 35,000 ft.”

He even brings his fellow pilots behind the scenes, explaining how the OCC fits into the broader system. Mentorship has naturally become part of his role as he helps newer pilots understand how airline operations work.

The two roles—crew services supervisor and pilot—overlap in more ways than one, but the lifestyle is different. OCC work requires rapid decisions and constant adjustments, while pilot life spreads troubleshooting across trips and reserve stretches. But for Bo, the transition felt natural and supported.

For now, Bo can be found building up his flight hours in the flight deck. He doesn’t take the journey or the view for granted.