Headmaster

Chesterton Academy of Mary Star of the Sea Melbourne, FL Job ID#: 16425177161 Posted September 4, 2026 Expires November 3, 2026 Category Secondary Education Terms Full-Time Employee Experience 0-2 Years Education Undergraduate Degree Base Pay Salary Send applications or inquiries to: admin@chestertonmarystar.org Apply by Email For your privacy and security, when applying for a job, never provide your social security number, credit card number or bank account information to a prospective employer. To use this website, you must accept and comply with our Terms of Service. Report This Listing Job Description Founding Headmaster - Melbourne, FL Chesterton Academy of Mary Star of the Sea (CAMSS) Location: Melbourne, FL Position: Full-time, on-site Compensation: Salary Job Summary Chesterton Academy of Mary Star of the Sea is seeking an exceptional Founding Headmaster to lead the academic, cultural, and spiritual development of a new Catholic classical high school in Melbourne, FL. Working in close partnership with the Executive Director, Board of Directors, faculty, families, and the Chesterton Schools Network, the Headmaster will play a central role in establishing a school where academic excellence, Catholic faith, and authentic community thrive together. This is a unique opportunity to shape a school from its earliest days. In addition to providing day-to-day academic and institutional leadership, the Founding Headmaster will help establish the CAMSS's vision, traditions, policies, faculty culture, and relationships with families and the broader community. We are looking for a mission-driven educational leader who is passionate about Catholic education, classical learning, and forming young people in truth, goodness, and virtue. Key Responsibilities As Founding Headmaster, You Will Establish the traditions, culture, routines, and identity of the Academy. Help develop school policies, procedures, academic standards, and faculty expectations. Recruit, hire, form, and onboard the CAMSS's founding faculty. Partner with the Board of Directors and Executive Director to ensure a successful school launch and sustainable long-term growth. Collaborate with the Chesterton Schools Network throughout the Academy's launch and formative years. Lead the academic program in accordance with the classical liberal arts tradition and the mission of Catholic education. Implement the Chesterton Schools Network curriculum while maintaining high standards of academic excellence. Provide instructional leadership through faculty supervision, coaching, evaluation, and professional development. Build strong, trusting partnerships with parents, recognizing them as the primary educators of their children. Foster a school culture characterized by trust, collaboration, hospitality, joy, and open communication. Serve as a visible ambassador for the Academy at admissions events, parish and diocesan gatherings, community events, and other public engagements. Headmasters may be required to teach additional course sections for extra compensation. Qualifications Bachelor's degree required. Advanced degree in Education, Educational Leadership, Theology, or a related field strongly preferred. Demonstrated leadership experience in education or a related setting. Strong organizational and administrative skills, including the ability to manage budgets and allocate resources responsibly. Ability to ensure compliance with applicable educational regulations and standards. Commitment to the mission and principles of Catholic classical education. Experience in classical education, academic administration, and/or Catholic education is highly desirable. As a condition of employment, all employees of Chesterton Academy of Mary Star of the Sea 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. About Chesterton Academy Of Mary Star Of The Sea Chesterton Academy of Mary Star of the Sea is being founded on the conviction that academic excellence and faithful Catholic formation belong together. Rooted in the classical liberal arts and the teachings of the Catholic Church, CAMSS seeks to form young people who pursue truth, goodness, and beauty; develop a love for what is good; and are prepared to serve Christ and the common good with courage and joy. As Founding Headmaster, you will have the opportunity to help bring this vision to life and establish a school community that will serve Melbourne families for generations. How to Apply Applicants For The Founding Headmaster Position Should Submit A letter of interest explaining your connection to the mission of Chesterton Academy of Mary Star of the Sea and your qualifications for the position. A current resume or curriculum vitae. At least three professional references. Application materials should be submitted electronically to admin@chestertonmarystar.org Job Category: Education Send applications or inquiries to: admin@chestertonmarystar.org About The Employer Classical Catholic High School Similar Job Listings President Dominican High School Whitefish Bay, WI 2 days ago 9/02 Male Pro-Life Missionary (Paid) Generation Life Philadelphia, PA 4 days ago 8/31 Middle School Math Leave Replacement St. Rose of Lima School Massapequa, NY 7 days ago 8/28 Office Manager St. Jerome Institute Falls Church, VA 8 days ago 8/27 Director of Advancement Operations Mount De Sales Academy Catonsville, MD 8 days ago 8/27 Per Diem Substitute Teachers St. John the Baptist DHS West Islip, NY 9 days ago 8/26 Director of Boarding Admissions Maur Hill-Mount Academy Atchison, KS 14 days ago 8/21 Upper Level Spanish Teacher (Grades 9-12) Academy of the Holy Angels Demarest, NJ 15 days ago 8/20 Middle School Religion Teacher (Grades 5-8) Saint Mark Catholic Academy Brooklyn, NY 15 days ago 8/20 Middle School Teacher St Ignatius of Antioch Catholic School Yardley, PA 17 days ago 8/18