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Addressing the special leadership and funding challenges of a boarding and day school

Addressing the special leadership and funding challenges of a boarding and day school

March 1, 2024


In this episode of The Beacon Podcast, Lighthouse Counsel Senior Consultant Martha Ross talks with Ken Cheeseman, head of school at The Webb School, a boarding and day school in Bell Buckle, Tennessee.

In their discussion, Martha and Ken talk about:

  • The challenges of leadership and fund development at a boarding and day school. 
  • Helping students who are attending from other countries deal with isolation and loneliness.
  • Fostering camaraderie and a feeling of family among students of different backgrounds, as well as between day students and those who live on campus.

About our guest

Prior to Webb, Ken Cheeseman 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, Tennessee, and served in various leadership roles at TMI Episcopal in San Antonio, Texas, McCallie School in Chattanooga, Tennessee, and Woodberry Forest School in Orange, Virginia. 

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