Webster Trenchard

Webster Trenchard serves as the Associate Head of School and Dean of Academic Affairs at The Loomis Chaffee School since 2000, overseeing the curriculum and various academic departments while managing multiple direct reports, including the directors of academic and extracurricular initiatives. Prior roles include Director of College Guidance and Associate Director of College Guidance at Amherst College, where participation in the admissions committee occurred during a sabbatical from Loomis Chaffee. Additionally, Trenchard has experience as a teacher, college counselor, and coach at The Masters School and Western Reserve Academy, as well as an Admissions Counselor and Head Lacrosse Coach at Sacred Heart University. Webster Trenchard holds an M.A. in Liberal Studies with a focus on Creative Writing from Dartmouth College and a B.A. in English from Amherst College, complemented by a foundational education at Western Reserve Academy.