Administrative Model The Headmaster and the Executive Director lead the administrative team at Chesterton Academy. This model of school administration is one of equality and consensus with both specific and shared responsibilities. The Headmaster is responsible for the instructional leadership of the school, as well as hiring and supervision of faculty, the curriculum, and student life. The Executive Director is responsible for the business aspects of the administration including budgeting and finances, human resources, fundraising, strategic planning, public relations, building facility, and is the key liaison to the Board of Directors. These co-leaders share responsibilities for nurturing and maintaining the mission and traditions of the school and ensuring fidelity to the Magisterium. Both administrators are hired by and report directly to the Board of Directors. Position Requirements 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 curriculum, instructional leadership of the school, hiring and supervision of faculty, 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. Minimal Requirements Education: Masters degree in Education or related field Experience: Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising. The candidate must be a practicing Catholic and willing to take the Oath of Fidelity to the Magisterium. Application Process and Deadline Please submit a resume or curriculum vitae a portfolio of related work samples, and an educational/leadership philosophy statement via email to by July 13th or until the position is filled. About the Employer Chesterton Academy is a joyful, pro-family, and independent high school offering an integrated, classical 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.

How to Apply/Who to Contact

Please send your curriculum vitae and cover letter to by July 25th.