Cheshire Academy

Head of School
Start Date: July 1, 2025

Co-ed, Grades 9-PG College Preparatory Boarding and Day School, 362 Students
10 Main St, Cheshire, CT


Cheshire Academy is an internationally-minded college preparatory school that challenges its students to maximize their potential by developing the confidence, character, and critical thinking skills that enable them to thrive as global citizens.

Pillars of Bowden

Cheshire Academy strives to uphold the values of belonging, collaboration, engagement, and growth. These core values are born of and buoyed by the simple yet powerful Pillars of Bowden: Respect, Responsibility, Caring, Civility, Citizenship, Morality, Fairness, and Trustworthiness, each of which is represented by one of the eight pillars of Bowden Hall, one of the oldest schoolhouses in continuous use in the United States.

About Cheshire Academy

Cheshire Academy (CA) is a college preparatory, coed boarding and day school for 362 students in grades 9-12 and postgraduates. Founded in 1794 as The Episcopal Academy of Connecticut, a boarding school for young men, it is one of the oldest boarding schools in the country. In the 19th century the school became co-educational, and, in spite of its affiliation with the Episcopal Church, allowed students to practice the religions of their families. In the 1850s it became the first private educational institution in the U.S. to accept international students. In 1917, the school once again became a single gender school for young men, focusing on preparing students for nearby Yale University. Coeducation returned to stay in 1969. Today, Cheshire Academy is a school of a little more than 360 young men and women from around the world who thrive in a close-knit and student-centered learning environment that prepares them to thrive as global citizens.

The historic 104-acre campus is nestled in the bucolic yet central town of Cheshire, Connecticut. This friendly and safe town of approximately 30,000 is just two hours from both Boston and New York and 30 minutes from both Hartford and New Haven. Rich in educational opportunities, Connecticut boasts 91 private schools, most of them within easy driving distance from Cheshire. Many colleges and universities, too, are in the area, such as Quinnipiac, Yale, Southern Connecticut State University, Trinity, Wesleyan, and many more. Similarly, there is a broad array of museums and cultural activities to take advantage of, as well as beautiful parks, hiking trails, and beaches all within an hour’s drive.

One of Cheshire Academy’s points of pride is that it takes students where they are and supports their growth in a multicultural, globally-minded environment. In all facets of life at CA, emphasis is placed on self-reflection about personal and academic growth. CA believes all students are unique individuals with their own interests, styles, and needs. Faculty are keen to ensure students have an active role and voice in their learning and take ownership over creating work that reflects their passions and evolving world views. The Academy adopted the International Baccalaureate Diploma Programme (IBDP) in 2011. Its student-centered, interdisciplinary, and multi-modal approach and its philosophy fit perfectly with the school’s mission.

About the Position

The Cheshire Academy Board of Trustees has launched the search for the school’s next Head of School, who will take office July 1, 2025. The next Head will have the opportunity to build on a long tradition of success, leveraging the school’s historical reputation as one of the oldest boarding schools in the country. The school provides an excellent academic program augmented and balanced by outstanding opportunities in athletics and the arts.

How to Apply

Candidates interested in this position are asked to submit the following materials in a single merged document, in the order listed: 

  • EC Candidate Summary Sheet (Contact a consultant, below, for this document) 
  • Letter of Interest, addressed to the Cheshire Academy Search Committee 
  • Current résumé
  • Statement of Educational Leadership philosophy
  • A list of five or more references with contact information (including phone numbers and email addresses)
  • EC Disclosure Form (Contact a consultant, below, for this document)

Please send any inquiries, nominations, referrals, or expressions of interest electronically and in confidence to:

Sally Mixsell, Partner

Mary Seppala, Partner

Listing Date: June 4, 2024