Joshua Leary joined Indian Mountain School as Chief Financial Officer in July 2026, overseeing the School’s financial and business operations. An IMS alumnus from the Class of 2009, Josh went on to attend Salisbury School before earning his bachelor’s degree in Finance from Quinnipiac University. Most recently, he served as a member of the business office at The Hotchkiss School.

Josh resides in Cheshire, Connecticut, with his fiancée, Amara, and their bernedoodle, Pio. Outside of work, he enjoys traveling, cooking, and is an avid movie buff. He is also a devoted fan of the Tampa Bay Buccaneers and the New York Yankees.