Head of School

Josh Wolman, who began his tenure as Country Day’s 11th head of school in July 2014, is a talented and seasoned school leader who has spent his entire career in independent education.

A graduate of The Park School outside Boston, Josh was a boarding student at The Hotchkiss School; he graduated from Colby College in 1991 with a B.A. in American Studies. He holds an M.A. in Educational Administration with a concentration in Private School Leadership from Teachers College at Columbia University, where he was a Barnes Fellow through the Klingenstein Center. He has worked in many different areas across school life at The Hotchkiss School, Potomac School in McLean, Virginia, and Columbia University.

Before coming to ACDS, Josh was Assistant Head of School for Admissions and Financial Aid at Sidwell Friends School, one of the nation’s leading day schools, starting there in 2000. This Quaker school exemplifies both the strong educational tradition of the Religious Society of Friends and the highly selective world of Washington, D.C. private-school admissions. He spent two years as Assistant Head of School for Advancement and External Relations at another independent school, Holland Hall in Tulsa.

Josh and his wife, Rachel, met while both were pursuing graduate degrees at Columbia University. The Wolmans have two children, both graduates of Aspen Country Day School.


Balance is a recurring theme in Wolman’s educational philosophy. He writes…

“I believe that the finest schools are places that balance both quality and humanity, high productivity and high sensitivity. We need to make certain that students work hard and enjoy their work; that we expect our students to be taught basic skills and allow for individual, creative expression; that we value individuality and community; work and play.”

Josh Wolman