The Character of Home®

Head of School Search

Ken Cheeseman will join Webb as Head of School in July 2020

A Letter from
Board Chair Vance Berry '72
Search Committee Chair
Farrar Vaughan '95

Dec. 11, 2019

Dear Webb Community,

Following a comprehensive national search, it is our pleasure to announce the unanimous approval by the Board of Trustees of Ken Cheeseman as our next Head of School.

From the beginning, Ken expressed an “excitement about what is possible to achieve with The Webb School team and a deep sense of appreciation for the mission, values, and history of the school.” He added that it would be a “distinct honor to partner with The Webb School Board of Trustees and lead and serve the faculty and staff to powerfully live out this mission” on behalf of the alumni and current and future students.

Ken is a graduate of University of Virginia with a Bachelor of Arts in English and Economics and received a Master of Education in Curriculum Leadership from Lipscomb University.

He brings extensive experience and expertise with education in independent day and boarding schools, strategic planning, policy setting, admissions and fundraising. He is currently serving as Head of School of Fort Worth Christian School in Fort Worth, Texas. Prior to that, he held positions of Head of School and Academic Dean, respectively, at St. Paul Christian Academy and Brentwood Academy, both in Nashville, and served in various leadership roles at TMI Episcopal in San Antonio, Texas, McCallie School in Chattanooga, Tenn., and Woodberry Forest School, Orange, Va.

Ken’s passion for education, experience and significant leadership qualities, are enhanced by his idea that “two key elements in effectively leading a school are serving the teachers and staff in ways that maximize their talents and creating powerful and effective ways for partnership between parents, teachers, administration, alumni and friends of the school.”

Watching this process unfold has been a very affirming experience for the school and for us personally as alumni. Ken’s background fits with our goals to have Webb be successful in every aspect of the educational experience. We, as well as our colleagues, look forward to a great partnership. Our school is in a strong position, and we look forward to building on a firm foundation.         

As The Webb School celebrates its 150th Anniversary in 2019-2020 and we continue to plan for the future, Ken will officially join us in July 2020. In the coming months, we will introduce him and his family to the Webb Community. We hope you will join us as we give them a warm welcome. Until then, for additional information, please visit our Head of School announcement page at


Vance Berry ’72
Chair, Board of Trustees

Farrar Vaughan ’95
Chair, Head of School Search Committee, Trustee