Leadership & Vision

Q & A with CCA’s Head of School

Jeffrey Thompson was recently appointed Cape Cod Academy’s new Head of School. An accomplished business leader and entrepreneur, Mr. Thompson has served as Cape Cod Academy’s Director of Advancement and Director of Admissions. A graduate of Trinity College, Mr. Thompson is an active member of the greater Cape Cod community and currently resides in Harwich with his wife and their two children.
Why did you take on this new role at Cape Cod Academy?
It doesn’t take long to realize that Cape Cod Academy is a special place. We have outstanding faculty, beautiful facilities, and a truly wonderful community of students and families. Though my background in business is somewhat atypical for a school head, in the past few years I have been able to dive in and help create some new opportunities in partnership with the leadership team and many of our educators.
It is the success of that collaborative process that gave me the confidence that I can continue to work in tandem with our larger community to build on CCA’s mission and move the school forward in in innovative new ways to maintain our position as the best private school in the region.
What are your priorities in your first year as Head?
The biggest priority is growing the school. We have seen a spike in enrollment inquiries in all divisions. Our lower school students thrive in small class sizes where they greatly benefit from individual attention. Our middle school is uniquely designed to foster the educational and social development of adolescent students, and the richness of our upper school is unsurpassed. I look forward to sharing these attributes with prospective families.
Additionally, we are fortunate to have the best teachers in the region, and I plan to build on that going forward. I am meeting with groups of faculty, students, and parents to acquire a deeper understanding of everything that takes place in every department, classroom, and athletic field. Understanding the priorities from all viewpoints will help us chart a strategy and vision for the future that will support our teachers in creating a positive, lasting impact on each and every student that attends CCA.
What do you see at CCA that sets us apart from other schools in the area?
No surprise, it is our teachers. I am proud to work with them on a daily basis. But I would also add that the sense of community we foster and the impact that is likely to have on our young people long after they graduate is an understated, but critical part of the CCA experience.
How does your experience benefit CCA?
I really believe in the power and benefits of a private school education. I learned a lot from my father who was a teacher, coach, and then headmaster at a number of schools. I attended independent schools my entire life, and when I was in law school, I taught eighth-grade history classes. In addition to teaching, I have enjoyed wearing many hats in the private school sector, including coach, custodian, board member, parent volunteer, and chair of the Annual Fund. I hope that my personal commitment to advancing the independent school experience, combined with my business skills and belief that no head is successful without greater partners across the school community, will be the foundation for our future success.
Did you have a mentor or teacher who inspired your career or shared good advice with you?
Yes. While attending college, I worked for Governor Ella Grasso of Connecticut and served as the youngest field coordinator in President Carter’s re-election campaign. Ella Grasso gave me a piece of advice I will never forget: “Every decision is a fork in the road. You gather the information as best you can and move forward confidently. If you pick the wrong path, you can go back to the fork with the knowledge that you have learned from your experience. Because you are smart, you will make the right choice most of the time.”
What are some of your goals for the future of CCA?
Taking over the admissions role sparked a deep interest in me about how best we can engage students in their learning. I am committed to ensuring we have the largest incoming class possible and that CCA delivers the highest quality education.

Our leadership team

List of 5 members.

  • Photo of Jeffrey Thompson

    Jeffrey Thompson 

    Head of School and Director of Admissions
  • Photo of Lisa Kowaleski

    Lisa Kowaleski 

    Associate Head of School & Director of Lower School
  • Photo of Jessica Barbieri

    Jessica Barbieri 

    Assistant Head of School and Director of Upper & Middle School
  • Photo of Nancy Boyle

    Nancy Boyle 

    Director of Personalized Learning
  • Photo of Philip Kenney

    Philip Kenney 

    Director of Student Accountability, Humanities Faculty, Interim Director of Athletics
    508-428-5400 x 221
Cape Cod Academy is one of the only independent, co-educational, college preparatory schools serving students from kindergarten to grade 12 on Cape Cod.