The Chesterton Academy of Our Lady of Victory was founded in 2019 to offer a unique approach to classical education by focusing on providing transformation opportunities for our students in academics, the fine arts, outdoor adventure, and spiritual formation. Entering its third year of operation, our school expects full enrollment in the ninth, tenth, and eleventh grades this fall. The school is looking for its first Headmaster to lead its academic program. The Headmaster will be responsible for executing the school’s academic vision, philosophy of discipline, and mission, as well as overseeing the curriculum. The Headmaster will serve as a leader, and a fellow teacher, among an excellent faculty passionate about their disciplines, the love of the Lord, and sharing those loves with their students. The Headmaster will be responsible for the recruitment and hiring of teachers to join this intellectually rich environment, as well as their formation once they join the faculty.. The Headmaster will also be responsible for cultivating a joyful student culture conducive to our students’ formation as saints, through mentorship, discipline, and leadership by example. The Headmaster will supervise the faculty’s planning and execution of student life events, including the school’s House system, Formation Fridays, and other formation opportunities outside the classroom. The Headmaster will serve as the most public face of the school. This includes a critical admissions role, by serving as the chief evangelist for the school’s mission and vision among faculty and staff, current and prospective families, as well as among the greater Catholic community. 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 will report to the Board of Trustees, and in especially close collaboration with the Chairman of the Board. The Headmaster will work closely with the school’s Business Manager, and will support the Board’s efforts in the areas of communications and fundraising. This position will have room for professional growth within the School as the organization matures and the Headmaster demonstrates mastery of existing responsibilities and aptitude for additional ones. The Headmaster must be a practicing Roman Catholic and demonstrate a commitment to Catholic secondary education. The ideal candidate will possess previous experience in administration, with a preference for secondary school experience; familiarity with classical education and the teachings of the Catholic Church; and working knowledge of institutional advancement. A candidate must have a Bachelor's Degree (Master's Degree preferred) in education or a related field. Salary is competitive and commensurate with experience. The Chesterton Academy of Our Lady of Victory is a member of the Chesterton Schools Network. Founded in 2008 as a result of a grass-roots movement of parents, the Chesterton Schools Network offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, the schools develop complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about the growing national Chesterton Schools Network at

How to Apply/Who to Contact

Application Process: Please apply by emailing a cover letter and resume to our Board Chairman Mr. David Holman at