Headmaster’s Role Summary:
• The Headmaster is responsible for implementing the school’s vision, philosophy of discipline, and mission, as well as the Chesterton Schools Network
curriculum. The Headmaster is responsible for the hiring, mentoring, and training of teachers. Ultimately, the Headmaster is charged with forging strong relationships with students and creating an environment in which students are formed intellectually, spiritually, and in character.
• The Headmaster works in collaboration with the Executive Director and the
executive team, which is responsible for public relations, fundraising, student
life events, and recruiting. The Headmaster supports the team’s efforts in the areas of fundraising, marketing, admissions, and extracurricular activities.
He/She also works with the executive team on maintaining strong parent-school relationships and communication.
• A collaborative relationship between the Headmaster, the Executive Director,
and the Board is a requirement.
The Headmaster serves as our academic leader and is responsible for managing the policies, regulations, and procedures to ensure that students are supervised in a safe learning environment that adheres to our Catholic identity and meets the approved curriculum and mission of the school. The Headmaster and ultimately his/her family are the “face” of Chesterton Academy of The Holy Family. The Headmaster plays a
crucial role in recruiting and retaining students and families. He/she must inspire
students in the classroom and ignite support and enthusiasm for classical education among our faculty, parents, and stakeholders. To this end the Headmaster should be present in the classrooms and hallways of the school for the majority of the school day.
In addition to teaching responsibilities, the primary responsibilities of the Headmaster include forming the whole student, building the morale of the faculty, and protecting and implementing the Chesterton Schools Network Curriculum.


The Headmaster must be a practicing Roman Catholic and demonstrate a commitment to Catholic secondary education. The ideal candidate will possess teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy Schools and the teachings of the Catholic Church; and working knowledge of institutional advancement.

Salary is competitive and commensurate with experience.


Apply by emailing a cover letter and resume to our Board Chairman, Mr. Steven Wilson