Jay started his career in education at Nativity Prep, serving as a teacher from 2010-2012. He then worked for three years at Nashoba Brooks School in Concord, MA, where he taught Latin and served as the Dir. of Athletics & External Programs. Jay returned to Nativity in 2015 as Principal, and was appointed Head of School in 2019. Jay has a B.A. in Anthropology and Classical Civilization from Indiana University Bloomington, and was a Fellow in the Lynch Leadership Academy at Boston College in 2017.