The Founding Headmaster is entrusted with leading the academic, cultural, and spiritual life of Chesterton Academy of Jacksonville. Working alongside the Executive Director and Board of Directors, the Headmaster will help establish a school where academic excellence, Catholic faith, and authentic community flourish together.

The Headmaster is responsible for leading the school's academic program, cultivating its Catholic identity, developing faculty, supporting students, and establishing a school culture rooted in the mission of the Academy.

This is a founding leadership position. Beyond overseeing the daily life of the school, the Headmaster will help shape its long-term vision by hiring faculty, developing institutional practices, building relationships with families, and establishing traditions that reflect the mission of Chesterton Academy of Jacksonville.

If you're passionate about education and have a heart for leading a thriving school community, we'd love to hear from you!

Join us in shaping the future of Catholic classical education! Join a Joyfully Catholic, Classical High School Forming Saints and Scholars.

We are expanding as we enter our 12th school year, and we are accepting applications for the 2026-2027 academic year! We are looking for passionate and talented educators to join our dynamic faculty in the following subject areas:

• Mathematics & the Sciences

• Humanities, including History, Latin, and Literature
  
  Special Qualities & Characteristics
  • Passionate about the mission of Chesterton Academy and its three pillars: spiritual, intellectual, and virtue formation
  • Deep appreciation for the Catholic faith and a commitment to the teachings of the Church
  • Practicing Catholic willing to take an Oath of Fidelity to the Magisterium of the Roman Catholic Church
  • Strong initiative and desire to work in a highly collaborative environment
  • Excellent rapport with parents, students, and fellow staff members
  
  Compensation & Benefits
  • Competitive salary, commensurate with experience
  • 401(k) retirement savings plan, Healthcare Allowance
  • Generous paid time off, including approximately 26 PTO days for school holidays
  • Paid sick leave included in PTO policy
  • Annual professional development opportunity at the Chesterton Schools Network Summit Conference
  • Additional stipends available for coaching and extracurricular responsibilities
  
  If you feel called to teach truth, goodness, and beauty, we invite you to apply today and join a school dedicated to forming joyful leaders, faithful Catholics, and thoughtful scholars. This is more than a job — it's a vocation. Chesterton Academy of The Holy Family is a religious 501(c)3.
  
  Apply today online at: www.chestertonacademyoftheholyfamily.com/careers

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