Cape Cod Academy Appoints Jeffrey Thompson Head of School

Filed Under: Non Profit News

November 20, 2019…Osterville, MA… The Cape Cod Academy Board of Trustees today announced that Jeffrey Thompson was selected as the sixth Head of School. An accomplished business leader and entrepreneur, Mr. Thompson has served as Cape Cod Academy’s Director of Advancement since 2016 and Director of Admissions since summer 2019.
“Jeff brings a deep appreciation and understanding of independent schools along with an impressive set of business skills to this position,” said Joel Crowell, Chair of the Cape Cod Academy Board. “He has a genuine desire to strengthen Cape Cod Academy, and he has a strong affinity with the school’s mission to inspire the minds and hearts of students. We are excited to have him as the next leader of Cape Cod Academy.”
Mr. Thompson will succeed Interim Head of School, Chad Small, who will be available as a resource through the end of December. The school is incredibly grateful for the leadership Mr. Small provided. He was instrumental in leading the school to its re-accreditation with the New England Association of Schools and Colleges (NEASC). Mr. Small worked tirelessly with faculty and staff to carry out the school’s commitment to its mission and core values, always doing what is best for the students.
For the past twenty-plus years, Mr. Thompson has served in leadership roles at energy, real estate, and technology companies, where he was responsible for business leadership, external affairs, and growth strategies. He joined Cape Cod Academy’s senior administrative team in 2016 as Director of Advancement. In this role, he surpassed previous school fundraising efforts each year. He then assumed additional responsibilities as Director of Admissions, where he successfully demonstrated his keen ability to inspire current and prospective families.
“I am incredibly honored to be appointed to lead this truly special place where young people learn and grow, supported by the best educators in the region,” said Mr. Thompson. “I want to thank outgoing Head of School, Chad Small, for his many insights and guidance, our faculty and staff for their current and future partnership, and our students and their families for their continued investment in our community. Together, we are going to ensure that Cape Cod Academy remains the best independent school on Cape Cod and will meet the education needs of future generations.”
The Board was assisted in its search by Independent Thinking, a firm experienced in independent school leadership recruiting. Independent Thinking conducted a series of conversations with the board, faculty, staff, alumnae, and others to develop criteria for the Head of School search.
“Based on our assessment, we believe that Jeff is a strong candidate for Cape Cod Academy,” said Bill Lyons, Managing Partner of Independent Thinking. “He is an accomplished individual with a track record of success, as well as a genuine passion for the school, its team, and the students it serves. In partnership with CCA’s strong educational team well steeped in curricula, Jeff will bring a strategy and vision that puts the school in the best position for success.”
A graduate of Trinity College, Mr. Thompson is an active member of the greater Cape Cod community. Most recently, he served as Commodore of the West Dennis Yacht Club in West Dennis, MA. In addition to his professional experiences, Mr. Thompson has been active in numerous civic and non-profit organizations, including serving as the Annual Fund Chair at Saint Andrews School, Austin, TX and in various leadership roles on the board of the Norwood School in Bethesda, MD. Mr. Thompson currently resides in Harwich with his wife, Elissa Thompson, a cardiologist at Cape Cod Healthcare in Hyannis. They have two children.
Cape Cod Academy (CCA) is one of the only independent, co-educational, college preparatory schools serving students from kindergarten to grade 12 on Cape Cod. Founded in 1976, the school is located on a gorgeous 46-acre campus that features outdoor classrooms, multiple athletic fields, two gymnasiums, state-of-the art science labs, and a black box theatre. Our mission is to instill a love of learning in students as they pursue academic excellence and develop life skills in a safe, values-centered community. CCA students succeed inside and outside our classrooms to become inquisitive learners, leaders on the field, leaders in their communities, and eventually, leaders in our global community. One-hundred percent of Cape Cod Academy seniors are accepted to four-year colleges! For more information, visit

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