A Fond Farewell to Gayle Jessee

Carlisle Upper School Director Gayle Jessee retires after 25 years at the school.

Carlisle Upper School Director Gayle Jessee retires after 25 years at the school.

In the last 25 years, Gayle Jessee has worn many different hats at Carlisle School – teacher, coach, administrator, and most recently, Upper School Director. But after 25 years of serving students, Jessee has decided that now is the time to retire.

“It’s definitely a difficult decision, after 25 years,” Jessee said, “but it felt like the right time for me. With aging parents and a new three-month old granddaughter…I just don’t want to miss out.”

While family is the reason Jessee is retiring, it is coincidentally the reason she entered the field of education in the first place. Both of her daughters, Joanna Roye and Amanda Buckner, attended Carlisle from the first through 12th grade. When her oldest, Joanna, entered the first grade in 1990, Jessee started volunteering at the school by tutoring students through a supplemental reading program. Just a couple years later Jessee, who received her BA in Psychology from the University of Virginia, started teaching Psychology and Early American History full-time.

From those early days, her teaching role has expanded to a variety of subjects from math and English to film and psychology.

“Working with students energizes me,” she explained. “I enjoy being able to see things freshly through their eyes. The satisfaction I get seeing each class graduate – that’s the most rewarding part.”

Her love and passion for teaching have made her a versatile member of the Carlisle family, helping her fill voids in the classroom, but also in various administrative roles.

In addition to her current role as Assistant Head of School and Upper School Director, Jessee has served as the Athletic Director, the Lower and Middle School Director, and Curriculum Coordinator, among many other positions. Even with these demanding responsibilities, she also continued to teach.

“I’m a lifelong learner. I like to challenge myself,” she explained of her continually shifting positions. “The variety at Carlisle has given me the opportunity to stay here for so long.”

In all her roles, meeting the students’ needs has always been her focus. And it is a focus that has paid off, since every Carlisle graduate is accepted into a four-year college or university.

“Carlisle continues to strive to provide quality academic opportunities for our students,” she explained. “The fact that we offer students an exceptional educational experience – academics, athletics, and extracurriculars – means we have very well-rounded students. We want them to be successful not only in college, but also in life.”

As approaches to teaching and learning have changed, Jessee has helped implement many of the adjustments made to meet students’ needs. Recently Carlisle has replaced its focus on the International Baccalaureate Program with a renewed focus on Advanced Placement and Dual Enrollment courses to better serve the needs of its students. In the past five years alone, the Dual Enrollment candidates have grown from five to 50 students, and they now have the option of enrolling in the Academy for Engineering and Technology through New College Institute.

“I feel very proud to work with a group of teachers who are constantly adapting their teaching skills to the new environment,” Jessee said of her coworkers. “I want to just say a thank you to all the faculty and staff that has helped me over the years. It really has been a team effort, and I cherish the friendships I’ve developed.”

The feeling is certainly mutual. Tommy Hudgins, Carlisle’s Head of School, said, “During her time at Carlisle, Gayle has left her mark on virtually every program at the school. All constituencies know that she will move heaven and earth to help a student. There is no better ambassador for the student-centered environment at Carlisle than Gayle. We will miss her terribly.”

Jessee plans on working closely with her replacement Keith Dallas to ensure a smooth and seamless transition. “I know he will receive the cooperation and support from the teachers that I have received,” she said. “And I hope that he will try some fresh new approaches, because while change is hard, it’s also necessary to grow and prosper.”

This year’s closing exercises will be particularly bittersweet for Jessee as she shakes the hands of her last graduating class as they receive their diplomas, many of whom she witnessed start as preschoolers at Carlisle.

While this chapter at Carlisle closes, she still wants to keep her options open, possibly substitute teaching or even teaching a class or two down the road.

But for now, it’s her new role as grandmother that she wants to devote her energy to – that and her golf game.