Chesterton Academy of The Holy Family - Western Suburbs of Chicago, Illinois

About Chesterton Academy of The Holy Family

Chesterton Academy of The Holy Family is a pro-family high school located in the western suburbs of Chicago offering an integrated, college preparatory curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life.

Our Administrative Model

The Headmaster and the Executive Director lead the administrative team, which operates under the Board of Trustees at Chesterton Academy of The Holy Family. These co-leaders share the responsibilities of nurturing and maintaining the mission and traditions of the school, as well as ensuring fidelity to the Magisterium. Both administrators are hired by and report directly to the Board of Trustees.

Headmaster’s Role


  • 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 any 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 of The Holy Family and the teachings of the Catholic Church; and working knowledge of institutional advancement.


Salary is competitive and commensurate with experience.

Application Process

Apply by emailing a cover letter and resume to our Board Chairman Mr. Brenie Bowles at careers@cathf.com.

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