Head of School Search

Thomas W. Sheppard

Tom Sheppard’s thirty-three-year career in independent schools began in 1991 teaching social studies, coaching, and serving as a dorm parent at Perkiomen School in Pennsylvania.  After Perkiomen, Mr. Sheppard spent twenty-two years in lead admissions and enrollment roles at Trinity-Pawling School in New York, Stevenson School in Pebble Beach, California, and The Lawrenceville School in New Jersey.  Mr. Sheppard’s tenures at these prominent schools were marked by significant achievements in enrollment, marketing, and tuition revenue that earned him a national reputation.

Mr. Sheppard assumed his first headship in 2018 at the St. Andrew’s Episcopal School in Jackson, Mississippi, a PK-12 co-ed day school with 1,041 students. While Head of School at St. Andrew’s, Mr. Sheppard led one community-wide strategic planning process and began another, and oversaw more than $6 million of fundraising to support educational innovations, including investment in technology opportunities and early education. Mr. Sheppard also developed and directed the school’s first Diversity, Equity & Inclusion program overseen by a newly created full-time position. Under Mr. Sheppard’s leadership, the school partnered with Mississippi’s William Winter Institute to bring additional Diversity, Equity & Inclusion programming to the school.

In July 2021, Mr. Sheppard assumed a two-year interim headship at the Chadwick School, a K-12 co-ed independent day school with 865 students in Palos Verdes Peninsula, California.  Mr. Sheppard took on the important role of leading a splintered school community out of a tumultuous five-year period of leadership turnover and community turbulence. This interim headship has called for tremendous energy, creativity, and empathy to rebuild the school leadership team, reestablish trust with faculty and build programs to support their wellbeing and professional development, and set the school on a path to financial sustainability and strategic planning for the future.  Chadwick’s Board President has shared that Mr. Sheppard has done an outstanding job in this difficult role and is a “superb leader.”  Mr. Sheppard describes himself as a “systems thinker,” with an “approach to leadership . . . that emphasizes a commitment to building community.”

Mr. Sheppard is a product of an independent school education having graduated in 1987 from Severn School in Severna Park, Maryland.  He has a Bachelor of Arts in History from Washington and Lee University and a Master in Education in Educational Leadership from Lehigh University.

Tom and his wife of twenty-two years, Jennifer, have two children, a son attending Davidson College and a daughter in her senior year at boarding school in Delaware.  Jennifer Sheppard is a veteran leader in independent school admissions and financial aid, currently with Clarity Tuition.