Department: Dean's Office

Phillip Harris

Since 2019, Phil has worked at Steppingstone in Boston, where he started out as a support services advisor for 150 junior high school students and families. Most recently, he has served as the director of middle school success, leading the planning and implementation of college readiness curriculum and activities for 300 students and families. Phil earned his B.A. in Spanish…

Jason Sport

Having served as the dean of students at Austin Preparatory School for two years, Jason joined the dean’s office at Middlesex in 2019 after teaching history full time for a year. A graduate of Governor’s Academy, he first taught, coached, and served as a dorm parent at the Williston Northampton School before joining the faculty at the Gilman School. Jason…

Kathy Smithwick Swain

After graduating from Duke University with a B.A. in history, Kathy returned to campus as an assistant admissions officer, coach, and dorm assistant, fulfilling those roles for seven years. On earning her M.Ed. in independent school leadership from the University of Pennsylvania, she began teaching history as well, and in 2019, she took on another new set of responsibilities, moving…