Flight School Spotlight: Chesapeake Sport Pilot

A self-described, “crazy cat lady who runs a flight school,” Woods has been involved with Chesapeake Sport Pilot since it first opened—in 2006. She bought the flight school in 2016, despite dissents from individuals like her financial advisor. “Everybody advised me against buying a flight school,” Woods said. “It’s not a good thing to do, not if you want to make money.” But Woods had her reasons. “It’s kind of like buying an airplane” she said of her decision to purchase a flight school. “The only good reason to buy an airplane is because you want to own the airplane. There is no other way to justify it.”

After buying the school, Woods set out to make Chesapeake Sport Pilot a more profitable and productive operation, starting with securing a building for the school, followed by setting up a maintenance shop in the space—now staffed by three full-time and several part-time mechanics. Almost everyone on her staff of about 30 to 40 people is part time. That includes office staff, maintenance, even flight instructors, about whom Woods is very intentional when hiring. “I do not hire time-builder flight instructors,” Woods said. “My flight instructors are almost all retired from different branches of the military or airlines; some have other jobs on the weekends. Everybody that comes on the staff has to be here because they have a passion for teaching, and they have to want to be part of the community.”

Community. It’s a word used a lot by Woods to describe the atmosphere at Chesapeake Sport Pilot. Outside of the nearly 40 employees on the staff, Woods has somewhere between 60 and 80 volunteers. She said they run “all of our activities, our scouting events, and our news outreach programs, and all of our tents and booths at airshows and things.” Most of them are previous clients. “They don’t ever leave,” Woods said. It’s this continuation of community—the essence of the flight school that almost mimics a flying club—that keeps them coming back again and again.

Chesapeake Sport Pilot caters to a specific clientele, according to Woods, who noted that her flight school is not the best place for aspiring airline pilots, but rather for pilots looking to have fun in airplanes. “We sell fun,” Woods said. “I tell my friends and family I run an adult toy store.”

The school markets to pilots who are looking for fun, such as those who are pursuing flight later in life or rusty pilots hoping to get back in the air.

The success of the flight school, recognized as a distinguished flight school in AOPA’s Flight Training Experience Awards every year since the awards’ inception, seems to stem from an understanding of its niche clientele and the commitment to foster a community. “People come here to get back into flying or start flying and to join a community,” Woods said. “They can come and have fun and just enjoy being a pilot and hanging out with other people who are pilots, making friends who are pilots, and just be part of our group.”