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Meet Our Head of School

Ken Cheeseman - Webb Photo 2

Ken Cheeseman officially began his responsibilities as Webb's Head of School on July 1, 2020, but in reality, he has often thought of Webb throughout his career. At various stages, he has been aware of Webb's storied history, its success and its  reputation for education excellence.

"Even during my last year as an undergraduate at University of Virginia when I was looking for my first job in   education, I was intrigued by the success of The Webb School. During several of my interviews at other schools, I heard people talk about Sawney Webb. So, for more than 30 years, I have connected the name Webb with excellence in independent education. Serving as the President of the Board for the Tennessee Association of Independent Schools, I was often reminded of the high quality of education that defined Webb."

Webb's reputation, leading a day/boarding school -- a combination that he found "very appealing" early in his career -- and returning to Tennessee, attracted him to Webb during the 2019 head of school search. He was named as the next head in December and brings extensive experience and expertise with education in independent day and boarding schools, strategic planning, policy setting, admissions and fundraising. He succeeds Ray Broadhead, who served in the position for the last decade.

"I firmly believe that Webb can be the best small boarding/day school in the Southeast and perhaps the country in instilling a love for and excellence in the three A's: academics, arts, and athletics. This kind of complete student experience in the beautiful setting of The Webb School can be unparalleled," Cheeseman offered. "Since my earliest days in education, I have seen the combination of clear, high standards aspired to within the deep, healthy relationships between teachers/coaches and students produce the best, most transformative learning."

Cheeseman Family - Photo

In his leisure time, Webb's new leader enjoys running, walking and hiking. "You will often find me running with Cathy, my wife, or trying unsuccessfully to keep up with one of our four children on a run. I love to travel and experience new places and cultures. You will notice as you glance at my bookshelves that I love to read -- a couple of hours with a good book is always time well spent. Playing board games or watching a movie with family is a favorite as well."

Prior to Webb, he served as Head of School of Fort Worth Christian School in Fort Worth, Texas. He has also held positions of Head of School and Academic Dean, respectively, at St. Paul Christian Academy and Brentwood Academy, both in Nashville, Tenn., and served in various leadership roles at TMI Episcopal in San Antonio, Texas, McCallie School in Chattanooga, Tenn., and Woodberry Forest School in Orange, Va. He 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 and Cathy have four children, Allison 24, Claire 22, Carter 19 and Abby Faith 13.