Headmaster - Jacksonville, FLSociety of Gilbert Keith Chesterton

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!

Few educational leadership opportunities offer the chance to shape a school from its very beginning. As the Founding Headmaster of Chesterton Academy of Jacksonville, you will work alongside the Board of Directors, Executive Director, faculty, families, and the Chesterton Schools Network to establish the traditions, culture, academic excellence, and Catholic identity that will define the Academy for generations to come. This role calls for a leader who is energized by building, collaborating, and investing in a mission that extends well beyond the opening of the school's first academic year.

As Founding Headmaster, responsibilities include:

●      Helping establish the traditions, culture, and rhythms of the Academy.

●      Assisting in the development of school policies, procedures, and faculty expectations.

●      Leading the recruitment, hiring, formation, and onboarding of the Academy's founding faculty.  

●      Collaborating with the Board of Directors and Executive Director to support the successful opening and sustainable growth of the Academy.

●      Working closely with the Chesterton Schools Network during the Academy's launch and early years.

●      Ensuring that the Academy's academic program reflects the rigor of the classical liberal arts tradition and the mission of Catholic education.

●      Implementing the curriculum of the Chesterton Schools Network while maintaining high standards of academic excellence.

●      Providing instructional leadership through the supervision, coaching, evaluation, and professional growth of faculty.

●      Building strong partnerships with parents as the primary educators of their children.

●      Cultivating a school culture marked by trust, collaboration, hospitality, and open communication.

●      Serving as a visible ambassador for the Academy by representing the school at admissions events, parish and diocesan gatherings, community events, and other public engagements.

A advanced degree in Education, Educational Leadership, Theology, or a related field is strongly preferred. Demonstrated ability to manage budgets, allocate resources effectively, and ensure compliance with educational regulations and standards.

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.

Chesterton Academy of Jacksonville is being founded on the belief that academic excellence and faithful Catholic formation are inseparable. Rooted in the classical liberal arts and the teachings of the Catholic Church, we seek to cultivate students who pursue truth, goodness, and beauty, who love what is good, and who are prepared to serve Christ and the common good with courage and joy. 

Individuals interested in the Founding Headmaster position are invited to submit the following materials: 

• A letter of interest describing your interest in the mission of Chesterton Academy of Jacksonville and your qualifications for the role. 

• A current résumé or curriculum vitae. 

• A list of at least three professional references. 

Application materials should be submitted electronically to: info@chestertonjax.org.