Dolph Clinton named Cheshire Academy’s new associate head of school

May 16, 2022

Cheshire Academy is pleased to announce that Dolph Clinton has been named the school’s next associate head of school. 

A veteran of boarding schools and an accomplished independent school leader, Dolph has more than 20 years of experience working with students and leading several departments and initiatives, making him an excellent addition to the school’s leadership team.   

Dolph has held many roles within the schools where he has worked and lived, including most recently as assistant head of school for student life and dean of faculty at Brewster Academy (Wolfboro, New Hampshire). He previously served as director of institutional leadership at Brewster. 

Dolph also worked for 18 years at his high school alma mater, Pomfret School (Pomfret, Connecticut). At Pomfret, he taught, coached (football, basketball, softball), and held a variety of positions, including associate director of alumni engagement, dean of students, associate director of admissions, associate director of college counseling, and co-director of multicultural affairs. 

In addition to his work at independent schools, Dolph is an entrepreneur and innovative leader who founded and now consults for Deep Wells Group (Providence, Rhode Island), a boutique consulting firm that guides individuals and institutions through a process of deep engagement and discovery with a focus on making positive differences within their communities and the world. 

After graduating from Pomfret, Dolph earned a Bachelor of Arts degree in political science with a minor in philosophy from Gettysburg College, and a Master of Science in Education from the University of Pennsylvania. 

“I feel very fortunate to have found a new associate head of school who has such a breadth of experience and a tenure of success working with students, faculty, and parents,” Head of School Julie Anderson said. “Dolph is truly inspirational, and is someone who demonstrates a significant level of excitement and eagerness to serve as a positive role model at Cheshire Academy.” 

Dolph and his wife Rebecca Brooks joined the CA community on July 1. 


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