Headmaster

Chesterton Academy of Notre Dame; Melbourne, Northern (FL, KY); Hybrid; USD 90,000 - 120,000; Full time

Job summary

Chesterton Academy of Mary Star of the Sea in Melbourne, FL is seeking a Founding Headmaster to guide the new Catholic classical high school from its inception, shaping its academic and spiritual culture.

The Headmaster will collaborate with the Executive Director, Board, faculty, families, and the Chesterton Schools Network to establish traditions, policies, and a thriving school community rooted in truth, goodness, and virtue.

Qualifications

• Bachelor's degree required.
• Advanced degree in Education, Educational Leadership, Theology, or related field strongly preferred.
• Demonstrated leadership experience in education or related setting.
• Strong organizational and administrative skills, including budgeting and resource management.
• 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 desirable.

Responsibilities

• Establish traditions, culture, routines, and identity of the Academy.
• Develop school policies, procedures, academic standards, and faculty expectations.
• Recruit, hire, form, and onboard founding faculty.
• Partner with Board and Executive Director for launch and long-term growth.
• Collaborate with Chesterton Schools Network during launch and formative years.
• Lead the academic program in line with classical liberal arts and Catholic education.
• Implement curriculum while maintaining high academic standards.
• Provide instructional leadership through supervision, coaching, and professional development.
• Foster partnerships with parents as primary educators.
• Cultivate a culture of trust, collaboration, hospitality, and open communication.
• Serve as ambassador at admissions events and community gatherings.
• May teach additional sections for extra compensation.

Skills

Leadership

Administration

Budget management

Regulatory compliance

Catholic education

Education

Bachelor's degree

Advanced degree in Education or Theology

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

• 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.

Job Category: Education