The Headmaster of St. John Bosco Schools / Chesterton Academy of Rochester 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 mission and three pillars of the school. The Headmaster is responsible for the curriculum, instructional leadership of the school, hiring and supervision of instructional personnel, student life, discipline and related parent communication.

Position Summary
The Board of Directors appoints the Headmaster of SJBS/CAR. A collaborative relationship between the Executive Director and Headmaster is a requirement. 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) parent communications; (5) student admissions; (6) guidance; (7) other school operations.

Administrative Model
The Executive Director and Headmaster lead the administrative team at SJBS/CAR. This model of school administration is one of equality with both specific and shared responsibilities for nurturing and maintaining the mission and traditions of the school, and ensuring fidelity to the Magisterium.

The Headmaster is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional personnel, the curriculum, and student life.

The Executive Director is responsible for the business aspects of the administration including finances, human resources, fundraising, strategic planning, public relations, and building facility.


The Headmaster must be practicing Roman Catholic, possess the minimum of 5 years of educational leadership experience or a Master’s Degree in Administration or related field, and demonstrate a commitment to Catholic education. Salary starts at $50,000, commensurate with experience.



Apply at or email After a preliminary phone interview with a member of our search committee, we will arrange a group interview with school leadership. Finally, before hire the candidate will spend time with several faculty representatives to get a better feel for the SJBS/CAR mission and community.