Bridgton Academy
Diana J. Gleeson
March 21, 2023
Bridgton Academy hires Colby grad as next head of school
Bridgton Academy board of trustees has hired the head of Perkiomen School in Pennsburg, Pa., and Colby College graduate as its next head of school.
Diana Gleeson will succeed Marty Mooney, who has served as Bridgton Academy’s head of school since 2017. Mooney will step down at the end of the current school year to assume the role of head of school at Wyoming Seminary in Kingston, Pa.
When Gleeson assumes the role on July 1, she will be Bridgton Academy’s 49th headmaster since the school was founded in 1808.
“I began my career as a teacher and a coach — learning quickly that trust and fairness were cornerstones of creating a community within my team and classroom," Gleeson said. "It is clear that Bridgton’s mission and values align with who I am: Community, curiosity, sportsmanship, accountability and excellence. I have been living Bridgton’s values my entire career.”
Bridgton Academy offers a postgraduate year for young men. Its postgraduate program is a bridge year before the college experience. Overall, the academy has 180 students.
The postgraduate program is designed intentionally for those who have completed high school. The school does accept a small number of postgraduates that need to repeat their senior year. The school also welcomes seniors who are looking to complete their high school diploma at the academy.
Gleeson was chosen as head of school after a national search conducted by an educational consulting firm in Boston.
“The board selected Diana as our new head of school because she is the right person to lead the academy over the next decade,” said Board President Vicker DiGravio. “She has held significant leadership positions at several boarding and day schools over the past 30 years, including extensive experience with postgraduate students.”
Gleeson began her career at her alma mater, Vermont Academy, before serving on the faculty at Chapel Hill-Chauncy Hall School faculty in Waltham, Mass. She was a teacher, coach, dormitory parent, advisor, academic program director, dean of students and college counseling director for nearly two decades at three schools.
In Pennsylvania, she was assistant head of school for external affairs for the past six years at the Perkiomen School, where she created and implemented a data-driven enrollment and marketing strategy. She worked with the school’s executive leadership, faculty, coaches, alumni and donors to stabilize enrollment. Before becoming head of school, Gleeson served as assistant head of school for academic affairs, a position she held for two years.
She also worked as the Upper School Head at Allendale Columbia School in New York and Providence Country Day School.
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