By Grant Brown
The Future of Aviation Insurance Is Here
A few weeks ago, a coworker approached me, asking if I would be interested in a partnership in a Piper Cherokee so he could finish his flight training, and I could eventually teach my daughters. On paper, I probably wasn’t the obvious person to ask. I have more than 3,600 hours of flight time, a 20-year career in military combat aviation and now fly for a major air carrier. Long days at the FBO doing ground school and pattern work wasn’t at the top of my aviation bucket list at this point in my career if I’m honest.
But helping a friend finish his certificate, bringing affordable aviation to friends and family, and eventually owning an airplane that I could teach my kids in made the idea increasingly appealing. So we started shopping.
We found a nice Piper Cherokee not far from where we live. We took a friend’s Bonanza down to look at it, and the airplane was largely what we were looking for. There was one complication, the owner had stopped flying it and canceled the insurance about six months earlier. I wanted to fly the airplane before getting serious about buying it, so insurance quickly became one of our first hurdles.
A friend had recommended SkyWatch.AI, a 2016 privately held specialty InsurTech brokerage headquartered in Palo Alto, Calif. I went online expecting another lengthy process. Instead, I entered the Cherokee’s registration number, and the system automatically populated the aircraft information. I could easily add aviation memberships such as EAA, ALPA, and Piper Owners Society . The system pulled up our home airport, and I indicated the airplane would be hangered. The next step is what worried me, adding pilots. With my experience and ratings, I was confident I would be insurable at an affordable rate. Casey, however, being a student pilot with 50 hours, post solo, and with only a few hours in a Piper Cherokee, had me worried the premium would be astronomical. I added his information anyway.
With only a few clicks and less than 10 minutes time invested, I had an actual quote, with premium, and ability to adjust liability and physical damage coverage in real time. More importantly, the price was remarkably comparable other aviation insurance brokerage companies. I was able to download the quote and sample policy to investigate the fine print. That’s where I found something else I appreciated: The requirements for Casey were clear and reasonable. Casey would need five hours of Cherokee time in the previous 12 months and a CFI endorsement before acting as Pilot In Command. That aligned with our expectations of his transition from other trainer aircraft. The open pilot provision was also attractive. It potentially allowed some of our more experienced coworkers and friends to fly the Cherokee if they had 250 hours total time and 25 hours in make and model. Everything had gone so smoothly that I became suspicious I had missed something.
At the age and generation that I am, I decided to call and talk to a real person. I called the number I received in a courtesy email associated with my quote. A “Senior Account Manager” picked up at the second ring. We discussed the scenario and the specific quote. He helped to clarify with me that this would be a private ownership policy since it would have less than five members and not be used for commercial purposes. That meant instruction would be limited to the members on the policy but would wholly meet our intended use of the airplane.
What impressed me the most happened after we hung up. We had discussed a question regarding the open-pilot provision, and about an hour later he called me back. He had gone directly to the underwriters to verify the answer and wanted to make sure I understood it correctly. That combination caught my attention. The AI-driven system handled repetitive work with remarkable speed. When I had a nuanced question involving actual underwriting, there was a knowledgeable human available to answer it.
I ultimately went from needing insurance to paying the premium for an annual policy in less than 10 minutes of online work at a rate competitive with the traditional quotes I had researched.
Of course, buying an insurance policy and having a claim handled well are two very different measures of an insurance company, and I hope never to gain experience with the later. But as a first interaction with aviation insurance, SkyWatch demonstrated something our industry could use more of—technology eliminating friction without eliminating people. Now, if we can just get the AI to help Casey with his crosswind landings.
For more information about SkyWatch, visit
ABOUT THE AUTHOR
Grant Brown was active in USAF avionics maintenance out of high school. He left the AF to pursue becoming an F16 pilot and obtained an electrical engineering degree with minors in mathematics and astronomy. He joined the Air National Guard in 2007, and he earned F16 initial qualification, flight lead, mission commander, instructor, evaluator, director of operations and commander. Brown attended a USAF weapons instructor course in 2015 and taught there from 2016 to 2018. He has deployed five times to Iraq, Saudi Arabia, Kuwait, Afghanistan, and Korea. He has 3600 hours, about 250 in combat, primarily in a F16 Block 50 “Wild Weasel.” He joined a major air carrier in 2019 (right seat of the Triple 7). He owns a H35 Bonanza he recently upgraded and loves flying. His leadership philosophy is, “Listen, Support, Solve” and his go-to phrase is “Just Do.” Brown has known his wife since 2nd grade and has two daughters, Lucy, 15, and Heidi, 10
