Tom Lovett was named Headmaster of the St. Johnsbury Academy in 2001. Prior to that, he worked at the Academy in various capacities including Academic Dean, Assistant Academic Dean, English Department Chair, Director of the Advanced Placement Institute, Tri-Chair of the capital campaign for the Center for the Arts, Advisor Team Leader, English Teacher, ESL Teacher, Football Coach, Baseball Coach, Public Speaking/Debate Coach, and Head Dorm Proctor. Tom received an AM in English Language and Literature from Brown University, a BA in English and Humanities from Providence College, and was named a Klingenstein Fellow. 

After stepping down as headmaster in 2020, Tom became the interim director of the Northeast Kingdom Collaborative, a non-profit organization dedicated to economic and community development in the region. He now serves as the Collaborative Board Chair. He also was appointed to the Vermont State Board of Education in 2020, and became the Chair of the Good Shepherd Catholic School Board that same year. He was ordained a permanent deacon in the Catholic Church in 2022 and serves on other non-profit boards. He continues to teach English part-time and coach football at St. Johnsbury and is involved in youth sports.