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Jay started his career in boarding schools in 1993 at Cheshire Academy in Cheshire, Connecticut. Teaching runs in his blood (both of his parents were educators), but what drew him to boarding school was the sense of community that he found—a community that reminded him of the small town in Maine where he grew up. After nine years at Cheshire Academy, Jay came to Cate in 2002 to pursue a teaching position that included classes in the history and English departments. Jay was the Dean of Students for four years, and he currently serves the School as the Assistant Head of School.

Beyond his duties at Cate, Jay enjoys baking bread, playing basketball, running, and reading. He lives on campus with his wife, Margot, and his three children, Molly, Olivia, and Charlie.