Founding Headmaster

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. The Headmaster reports to the Board of Directors. The ideal candidate will demonstrate:

• A vibrant Catholic faith and a commitment to living in accordance with the teachings of the Church.
• A deep commitment to the mission of Catholic education and the formation of the whole person.
• An appreciation for classical liberal education and a willingness to embrace the mission and educational philosophy of the Chesterton Schools Network.
• Integrity, humility, and sound judgment in leadership and decision-making.
• The ability to inspire confidence, build trust, and cultivate meaningful relationships with students, families, faculty, clergy, and the broader community.
• As a condition of employment, all employees of Chesterton Academy of Jacksonville are required to take the Oath of Fidelity and affirm their commitment to faithfully uphold the teachings of the Catholic Church in accordance with the Magisterium.

Professional Qualifications:

• Bachelor's degree required. Graduate study or advanced preparation in education, leadership, theology, or a related field is preferred.
• Significant experience in Catholic education, with prior school leadership experience preferred.
• Success as an instructional leader through faculty formation, academic program development, and the ability to build a joyful, mission-driven school culture.
• Ability to recruit, develop, and retain outstanding faculty while fostering a collaborative culture of professional growth.
• Strong communication, organizational, and interpersonal skills, with the ability to build meaningful relationships with students, families, faculty, and community partners.

Compensation: $70,000+ per year, including some teaching duties, depending on experience. Interested candidates are invited to submit: A letter of interest describing your interest in the mission and your qualifications. A current resume or curriculum vitae. A list of at least three professional references. Applications will be reviewed on a rolling basis. Please submit materials electronically to [REMOVED - SEE ORIGINAL LISTING]