Insurer credits training, data; welcomes pistons

Launched in 2025 offering coverage in five states, 5X5  now underwrites policies in 38 states with plans to continue expansion "quickly" into 48 states. The company's new partnership with Sporty's Pilot Shop (which purchased PilotWorkshops in 2025) and PilotWorkshops benefits policy holders with up to a 20-percent premium credit for completion of recurring training.

In June, the aviation insurance startup hired Managing Director Doug Tibbs away from AXA XL, where he had worked for 14 years and most recently served as vice president and underwriting manager for general aviation. Tibbs said in an interview that 5X5's direct-to-consumer business model was part of the new job's appeal, along with its implementation of underwriting that factors training and data (a majority of policyholders have agreed to share flight data with the company "in exchange for underwriting that reflects how they actually fly," the company noted in a press release).

Tibbs said this concept of rewarding safe behavior had been on his mind for a long time.

"The idea of being selective from an underwriting standpoint, focused on pilots who are going above and beyond, I had in the back of my mind that, wow, this must really work. Like the numbers are probably good, but I never envisioned … how good they would be. I just figured it would be a little bit better," Tibbs said. While he declined to say exactly how many policies the company has written in its first year of operation, the data has impressed him. "It is wild how positive the numbers are. To date, we've not had one single accident as a result of pilot error. Knock on wood."

5X5's decision to initially focus offerings for jet and turboprop customers was a decision based on two key factors: The aircraft in those groups typically have the most advanced technology, including data logging capabilities, and owners' groups that have developed robust recurrent training programs. Tibbs said that Sporty's and PilotWorkshops offer similar training opportunities for newer piston airplanes that may not have owners' groups with the resources to provide analogous training. Generally speaking, the company seeks to welcome owners of Cirrus, Cessna, Diamond, Piper, and other brands of technologically advanced aircraft that are up to around 25 years old.

"We had to identify a way to help those piston aircraft owners, kind of incentivize them to get a discount, but also, you know, we're trying to promote safety," Tibbs said. "And that's a big part of what our DNA is, is to try to get people to do more and get rewarded for it. And, you know, it's a fairly simple business model, but it's one that makes sense in our industry."

Insurance premium credits are offered to pilots of piston aircraft, including a 5-percent premium credit for completing a qualified annual online proficiency course created by Sporty's and PilotWorkshops, with an additional 5-percent credit for completing 10 or more VFR or IFR Mastery scenario-based workshops during the year. These credits can stack on top of the existing 10-percent premium credit for participants in 5X5's Safety Rewards program, the company said, bringing the total potential savings to 20 percent of the policy premium.

"Pilot proficiency is not something you check off a list and move on from," said Sporty’s President and CEO John Zimmerman, in a news release. "It requires ongoing learning, practice and a willingness to keep improving. This partnership demonstrates the value for pilots who prioritize critical recurrent training."

5X5 offers an "instant estimate tool" on its website, and was founded with a data-driven approach to pricing insurance that credits pilots for training and dispenses with arbitrary age limits. Selling policies directly to consumers, 5X5 extends its technological approach to flight data, with additional discounts available to customers willing to share detailed flight data that can be included in the underwriting model.

5X5's Chief Underwriter Jeff Rhodes told AOPA in 2025 that basing premiums on actual performance and training makes more sense than basing them on a birth date.

“We all know pilots who are 45 or 50 years old that don't have the ability to fly the airplane that they own,” he said. “And we know pilots who are in their 70s or beyond that are sharp as a tack and we would trust with our spouses or our children. I really feel that reliance on training partners and a regular evaluation of that pilot’s ability is a much better way to underwrite and not an arbitrary cutoff. You know, we’re not just an insurance company for older pilots, but I think that a lot of them will find a home with us where they’ve been turned away by others.”