Headmaster

Chesterton Academy of Jacksonville seeks an exceptional Catholic educational leader to serve as its Founding Headmaster. This is a rare opportunity to help establish a new classical liberal arts high school rooted in the Catholic tradition and the educational philosophy of the Chesterton Schools Network. Working alongside the Board of Directors, Executive Director, and founding faculty, the Headmaster will shape the academic program, school culture, and Catholic identity of an institution that will serve students and families in Northeast Florida for generations to come. The ideal candidate is a faithful Catholic, an accomplished instructional leader, and a collaborative servant leader with a passion for forming young people in truth, goodness, and beauty. Responsibilities include providing academic leadership, mentoring and developing faculty, fostering a joyful and mission-driven school culture, partnering with families and the broader Catholic community, and helping guide the successful launch and long-term growth of the Academy. This is more than a leadership position, it is an opportunity to help build a lasting Catholic institution from the ground up. Candidates who are inspired by the mission of classical Catholic education and called to lead with faith, humility, and vision are encouraged to apply. To learn more and submit application materials, please visit or email View email address on click.appcast.io. #J-18808-Ljbffr Chesterton Academy of Jacksonville