Local resident Tyler Flagg founded Flying Company to connect aircraft owners and operators with the right pilot to navigate important trips.

The company operates a software platform that handles scheduling, contracts and payment processing for contract pilots.

Flagg compared his operation to a similar concept called Care.com that connects families with caregivers. “But instead of hiring babysitters, you’re hiring professional pilots.”

“When a pilot is needed, the operator creates a trip,” Flagg said. “They select the aircraft, crew requirements, and itinerary. That trip is automatically sent to pilots on the platform who are qualified for that specific aircraft.”

After that, Flagg said, pilots submit quotes for their services. Contract pilots are typically paid per day. Rates can range from about $1,000 per day for smaller turboprops to $4,000 or more per day for long-range international business jets.

“Once quotes are submitted, operators use a dashboard to assess candidates,” he said. “Messaging, contracts and payment processing are all handled through the platform.”

While Flagg is based in Bentonville, Flying Company is not restricted to just those who live in the Northwest Arkansas region.

“Flying Company isn’t a local-only business, but there are several professional pilots based in Northwest Arkansas who maintain profiles on the platform,” Flagg said. “There are also aircraft operators and management companies in the region that use us to manage their staffing needs.”

Flagg’s resume includes 14 years as a Special Operations pilot in the United States Air Force. Over that time, Flagg said he was deployed multiple times and flew operationally in 67 countries before serving in a variety of leadership and instructional roles.

“By the time I left the military, I felt very comfortable managing aircraft both technically and administratively,” Flagg said. “After separating from the Air Force, I took a job flying and managing a private business jet in Bentonville, which is what brought my family to Northwest Arkansas.”

After taking on this role, Flagg said he quickly realized that managing a private jet is very different from managing military aircraft. So, he spent time learning regulations and other requirements for running a flight-focused business.

“I got comfortable with most of that fast,” he said. “But one persistent problem kept coming up: Finding qualified pilots when I needed additional help.”

While searching for the best and most qualified pilots, Flagg said he was surprised to discover that many operators source pilots through informal channels, such as Facebook groups.

“I didn’t even have Facebook at the time,” Flagg said. “More importantly, it felt inefficient and risky for something as safety-critical as aviation. Finding a name is one thing, properly assessing and vetting a pilot is another entirely.”

More focus is placed on hiring a safe pilot, he said, including verification of certificates and experience, coordinating insurance approval, managing paperwork, and sharing aircraft information.

In March 2023, Flagg launched the first iteration of Flying Company and said he quickly realized he was onto something.

“It became clear I’d touched a nerve,” he said. “Pilots, aircraft owners, schedulers, and managers began reaching out, often with long messages describing how frustrating the existing process was and how much room there was for improvement. Those conversations directly shaped the platform that exists today.”

That clear demand has helped Flying Company grow to include multiple business jets across popular models, including Pilatus, Embraer, Dassault, Bombardier and Gulfstream. Flagg now works with management companies and Fortune 100 flight departments to staff their flights.

Lindsay Dyer, president of aviation scheduling service L/D Aviation Services Inc., applauds what Flagg has created.

“I’m so excited about this for the industry,” Dyer said. “This feels like to me it will be a game-changer for my job. I appreciate how it’s going to cut down the amount of work and time it takes to find pilots on our side.”

Derek Mentzer, a seasoned pilot, said he is ecstatic with the Flying Company because it removes friction to help him secure more gigs.

“Tyler has solved the problem that has beleaguered contract crews and operators alike,” Mentzer said. “It has empowered crews to provide more tailored and conscientious service to those who hire them.”