Cape Cod Academy Appoints Jeffrey Thompson Head of School

I am pleased to announce that the Board of Trustees has selected Jeffrey Thompson, our current Director of Advancement and Admissions, as our new Head of School. The vote of the Board was unanimous, reflecting our confidence in Jeff’s strong leadership and business skills, his commitment to partnering with our outstanding team of educators, and his true appreciation for all the many qualities that make Cape Cod Academy special.

Before I share more information on how we got here, I want to pause and, on behalf of the entire Board, thank Chad Small for his interim leadership. He has been outstanding in his role, equally committed to the educational and personal growth of Cape Cod Academy’s students and the success of its faculty and staff. His flexibility, insights, and focus have been a real asset to us, and we are grateful for his leadership.

As many of you know, the Board engaged Independent Thinking (a firm experienced in independent school leadership recruiting) to assist us in our search for the next Head of School. The goal was to have an inclusive search, and Independent Thinking conducted a number of sessions with our board, faculty, staff, alumnae, and others to gain insights into the qualities needed for this role. Based on this work and the field of candidates, Independent Thinking offered the strong recommendation that the Board move forward with Jeff immediately.

We agreed, for a number of reasons. First and foremost, Jeff is a proven leader with strong administrative and business skills who recognizes the importance of fostering a strong team united under a common mission. Second, in his tenure at Cape Cod Academy, Jeff has built positive relationships across our community — with faculty and staff, students and their families, alumnae and supporters. Finally, he has a vision for Cape Cod Academy’s future success which builds on our historic strengths and our dynamic independent school environment.

In some ways, Jeff’s resume is atypical for an independent school leader. His most recent roles included leadership positions in energy, real estate, and technology companies. However, given Cape Cod Academy’s strong and stable educational leadership and staff, many of our priority needs are on the operational side. Jeff has already been a strong partner to the board in building our enrollment, developing strategies for managing the EduBoston challenges, increasing fundraising, and future planning. We are confident that Jeff will maintain our high standards and ambitions for the Cape Cod Academy community and support our mission: fostering a life-long drive to learn, grow, and make a difference in the world.
Thank you for joining me in thanking Chad for his leadership and welcoming Jeff to his new role.


Joel Crowell P ‘08
Chair of the Board of Trustees
Cape Cod Academy
Cape Cod Academy is one of the only independent, co-educational, college preparatory schools serving students from kindergarten to grade 12 on Cape Cod.