Bolles alumnus Brooks Fleming ’92 will step into his new position of Head of Upper School at Community School of Naples (CSN) in Florida, starting July 1.

After earning degrees from Brown University (B.A. in English and American Literature) and Columbia University (M.A. in Independent School Leadership), including a spell playing football at Brown, Fleming taught English and held leadership positions at independent schools such as the Episcopal School of Houston (2001-2010) and Pace Academy in Atlanta (2010-2017). In both schools, Fleming also coached football and soccer.

He joined CSN as Upper School Dean of Academics in July 2017 and was appointed to the position of Assistant Head of Upper School in 2023.