Diana J. Gleeson

Diana Gleeson currently serves as the Head of School at Bridgton Academy, a position held since July 2023. Prior to this role, Diana Gleeson worked at Perkiomen School from July 2015 to June 2023, where responsibilities included Assistant Head of School for External Affairs and Assistant Headmaster for Academic Affairs. Additional experience includes a tenure as Head of Upper School at Allendale Columbia School from July 2009 to June 2015 and multiple positions at Providence Country Day School, including Director of Upper School and Dean of Students from September 2001 to June 2009. Diana Gleeson’s earlier roles include Dean of Students and Director of Residential Life at Chapel Hill-Chauncy Hall School and Biology Teacher at both Chapel Hill-Chauncy Hall School and Vermont Academy. Educational credentials include a Global Competence Certificate from Teachers College, Columbia University, and a Bachelor of Arts in English Language and Literature from Colby College.