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Chesterton Academy of Rochester

Chesterton Academy of Rochester is a classical school in upstate New York faithful to the Catholic Magisterium. Founded in 2014, we maintain a strong and robust sacramental life meant to be meaningful to each scholar as well as to faculty and staff. It includes daily Mass, frequent opportunities for confession, a number of retreats, and various devotional activities. We just moved into a new building, which offers room to grow enrollment and expand in-house activities, and we are seeking a headmaster to join us in our next phase of development.

Feb 16, 2026
Full time
Headmaster
Chesterton Academy of Rochester
SUMMARY The Headmaster serves as the educational leader, responsible for managing the policies, regulations, and procedures to ensure that all students are supervised in a safe learning environment that adheres to our Catholic identity and meets the approved curricula and mission of the school. The Headmaster is responsible for the curricula, instructional leadership of the school, hiring and supervision of instructional personnel, student life, discipline and related parent communication. The headmaster must be practicing Roman Catholic, possess the minimum of a Master's Degree in Administration or related field, and demonstrate a commitment to Catholic secondary education. Salary is competitive and commensurate with experience. The Board of Directors appoints the Headmaster of Chesterton Academy. In addition to any teaching responsibilities, the duties of the Headmaster include: (1) curriculum and academic excellence; (2) instruction; (3) student life and discipline; (4)...