R. Highley Thompson
Partner
Head of School Search, Senior Administrator Search
Charlottesville, VA
As a search consultant, Highley had led searches for division head (upper, middle, and lower
school), athletic director, enrollment management, and college counseling, while also supporting a
number of head of school searches. He loves partnering with schools and their search committees
in these searches that will positively impact students’ experiences.
Highley spent 30 years in independent schools as a teacher, coach, and administrator before
becoming a search consultant. Right out of college, he returned to his alma mater (Severn School,
MD) to begin his career as a middle school math and Latin teacher, while coaching soccer and
lacrosse. Over the course of his sixteen years at the school, Highley transitioned to the upper
school, where he taught English and algebra, and became dean of students, academic dean, and
eventually the Upper School Head. After a stint as Head of the Upper School and Assistant Head of
School at Chestnut Hill Academy in Philadelphia (now Springside Chestnut Hill), Highley moved to
Thayer Academy in Braintree, MA, where he served as the Upper School Director for twelve years.
While in schools, Highley especially loved building community and attracting excellent teachers to
his schools.
Highley earned a B.A in English from Princeton University, where he was also a four-year member of
the men’s lacrosse team. He later earned an M.Ed. in Administration and Supervision from the
University of Virginia.
Residents of Charlottesville, VA, Highley and his wife Anne enjoy spending time with family,
cooking, traveling, hiking, and enjoying the amenities that the Charlottesville and UVA
community offers. They have two children, one in graduate school and the other in college.