Meet our Next Head of School

It is with great joy that we announce the Board of Trustees has unanimously and enthusiastically selected Kenneth C. Cheeseman as St. David's School's next Head of School.


After an extensive search and rigorous evaluation of exceptional candidates, we have the utmost confidence that we have found the individual who will best lead St. David’s School forward in its mission.

As we embark on this new chapter together, I am eager to collaborate with each member of the community—Board of Trustees, faculty, staff, parents, alumni and friends of the school—to further advance our mission and uphold the rich traditions that have long distinguished St. David's. Guided by our unwavering commitment to faith, virtue and knowledge, I am confident that we will continue to cultivate a learning environment where every student is empowered to flourish spiritually, academically, artistically and athletically with the kind of Christian character that will effectively lead the next generation.Ken Cheeseman

Ken Cheeseman received a Bachelor of Arts in English and economics from the University of Virginia and a Master of Education in curriculum development from Lipscomb University. He comes to St. David’s with a rich history of school leadership, including twenty-three years of experience as Head of School. 

Mr. Cheeseman began his career teaching English at Woodberry Forest School and McCallie School. He remained in the boarding school realm until he arrived at Nashville’s Brentwood Academy, where he served as Academic Dean. He served sixteen years as Head of St. Paul Christian Academy, a PreK-6th grade school. His next headship was at Fort Worth Christian School, a PS-12th grade day school. After fruitful years at FWC, Mr. Cheeseman was excited to move back to the southeast and lead The Webb School, a 6th-12th grade co-educational day and boarding school with a 154-year history of excellence. During his time at Webb, Mr. Cheeseman has effectively led his team in growing recruitment and retention of students, alumni development and engagement, and philanthropic enhancements. He has years of experience leading faculty, recruiting excellent teachers, supporting and growing fine arts and athletics, and fundraising. 

Mr. Cheeseman’s leadership philosophy is anchored in his deep Christian faith. A former colleague who worked closely with him shared, “He is authentically Christian. He is true to his faith and leads from that truth. Ken believes that Christian schools should operate with academic excellence as well as stay true to their Christian mission.”  This commitment to faith, virtue, and knowledge is why Mr. Cheeseman has long held St. David’s in high esteem. While reflecting on being a finalist in the 2006 Head of School search for St. David’s, he shared, “I fell in love with the mission of St. David’s and was excited to live and share the benefits of a community that embraced 2 Peter 1:5…” The opportunity to lead a school committed to academic excellence and faith and virtue formation resonates deeply with Mr. Cheeseman's passion for shaping the next generation.

Ken and his wife, Cathy, are delighted to relocate closer to their two oldest daughters. Allison and her husband live in High Point and joyfully welcomed their first child in March, while Claire and her husband currently reside in Fuquay-Varina. Allison and Claire were successful collegiate cross country and track athletes, as is their brother, Carter, who continues his running career for the Belmont Bruins while in graduate school. The Cheeseman’s youngest daughter, Abby Faith, is a rising senior in high school and is prayerfully considering which college to continue her academic and cross country and track career. Running runs in the family! No surprise, Ken and Cathy were both college cross country and track athletes. Cathy, one of the most decorated high school coaches in Tennessee history, loves coaching her beloved sport at Webb. As they complete their final year at Webb and enjoy Abby Faith’s senior year, they eagerly anticipate joining St. David’s community in June 2025. 

The St. David's School Board of Trustees is thankful for God's provision throughout the search for a new leader. Our thanks go to the Search Committee for its unwavering commitment to finding the best candidate. We are grateful to Jack Hall and Gerri Williams of CarterBaldwin Executive Search for their invaluable partnership. The board is immensely thankful to the St. David's community, the Leadership Team, and the Consultative Committee for their involvement in the search process and for providing valuable input and feedback. A special thanks to Kathy Bateman for her exceptional support. The board is deeply appreciative to St. David's School's faculty, staff, and families who have prayed for God's guidance and provision throughout the search.

Perhaps our deepest gratitude is for Matt Hillegass, who has graciously agreed to remain Head of School for the upcoming school year while Mr. Cheeseman completes his final year at Webb. Mr. Hillegass’s continued leadership is a tremendous blessing to our school as we transition to a new leader. To support Mr. Hillegass’s commitment to leading St. David’s while simultaneously pursuing family priorities already in motion, the board is partnering with him to structure this school year with a focus on maintaining the momentum of some key strategic priorities and bridging Mr. Cheeseman into the St. David’s community. Mr. Hillegass and Mr. Cheeseman are eager to partner together throughout this bridge year in preparation for fully passing the leadership baton to Mr. Cheeseman when he takes over as Head of School in June 2025.  

Please join us in our celebration and thanksgiving for God’s abundant provision to St. David’s School. 

With gratitude and joy,

The Board of Trustees



Search Updates

March 4, 2024
January 31, 2024
November 7, 2023
November 7, 2023
October 12, 2023
October 12, 2023
October 11, 2023
October 11, 2023


Search Committee Members

Anne Fletcher, Committee Chair

Joe Knott, Trustee

Paul Conway, Trustee

Donna McClatchey, Trustee

Dana Simpson, Trustee


Search Consultant

CarterBaldwin is an executive search firm that partners with corporate, nonprofit, and academic clients to build exceptional leadership teams. They pride themselves on having a highly experienced staff, an unrivaled search process, and an exceptional client and candidate experience. The firm is listed among a variety of rankings published by Hunt Scanlon Media, including its Top 50, Private Equity Power 100, and Top 50 Higher Education Search Firms.  Mr. Jack Hall, partner, and Dr. Gerri Williams, consultant, will lead the firm’s team working with St. David’s Head of School Search Committee.