Founding Headmaster - Chesterton Academy Ave Maria

Job Description

FOUNDING HEADMASTER
Chesterton Academy of Ave Maria
Ave Maria, Florida

Position: Founding Headmaster
Employment: Full-time, year-round
School Opening: August 2027
Preferred Start: As soon as practicable; exact date to be negotiated with the selected candidate
Starting Salary: $105,000+, negotiable and commensurate with experience
Application Deadline: October 9, 2026

Chesterton Academy of Ave Maria (CAAM) is seeking an experienced, mission-driven Founding Headmaster to serve as the educational, spiritual, and cultural leader of a new Catholic classical high school opening in Ave Maria, Florida, in August 2027.

This is a unique opportunity to help establish a school from its earliest days and shape the academic culture, faculty, traditions, and community that future generations of students will inherit.

CAAM is seeking more than an administrator. We are seeking a builder, teacher of teachers, cultural leader, and missionary educator who understands excellent teaching firsthand, can form and inspire faculty, communicates a compelling vision of Catholic classical education, and is excited by the opportunity to build something new.

The Opportunity:
Before the Academy opens, the Founding Headmaster will work closely with the Board of Directors to prepare CAAM for its inaugural academic year. Key priorities will include:

- Assist in the recruitment and formation of the founding faculty;

- Supporting admissions, enrollment, and prospective-family engagement;

- Working with the CAAM Board to develop academic policies, schedules, procedures, and school systems;

- Preparing for faithful implementation of the Chesterton Schools Network curriculum;

- Supporting advancement, donor engagement, and community outreach; and

- Helping establish the spiritual, academic, and cultural traditions of the Academy.

Once the school opens, the Headmaster will serve as the Academy's principal educational and instructional administrator, responsible for daily school operations, faculty leadership, student formation, academic excellence, and cultivation of a joyful and authentically Catholic culture.

Depending upon enrollment, staffing needs, and the candidate's background, the Headmaster may also maintain a limited teaching assignment.

Governance and Leadership:
Chesterton Academy of Ave Maria is governed by its local Board of Directors, composed of parents and community members entrusted with stewardship of the Academy's mission.

The Board establishes policy, strategic direction, institutional priorities, and the local framework within which the Academy operates. The Founding Headmaster reports directly to the Board, is accountable to it, and manages the daily academic, faculty, student-life, and administrative functions of the school within the Board's established framework and the educational model of the Chesterton Schools Network.

Key Responsibilities
The Founding Headmaster will:

- Serve as a visible and joyful witness to the Catholic faith and foster a school culture rooted in the teachings and sacramental life of the Catholic Church;

- Promote the intellectual, spiritual, moral, and human formation of students;

- Recruit, lead, mentor, evaluate, and form a strong faculty committed to Catholic classical education;

- Oversee faithful implementation of the Chesterton Schools Network curriculum and safeguard academic excellence;

- Provide leadership in classical pedagogy, Socratic discussion, integrated humanities, the liberal arts, mathematics, sciences, fine arts, languages, and theology;

- Oversee student formation, discipline, academic expectations, assessment, schedules, transcripts, and preparation for college and post-secondary life;

- Cultivate a school culture marked by joy, charity, personal relationships, hospitality, high expectations, and meaningful adult presence;

- Establish thoughtful norms concerning technology, phones, artificial intelligence, and digital media;

- Build strong relationships with students, parents, faculty, clergy, benefactors, and the broader community;

- Support admissions, enrollment, advancement, fundraising, donor engagement, and community outreach; and

- Provide regular reporting, recommendations, and timely information to the Board.

The Ideal Candidate
CAAM seeks a leader who:

- Is a practicing Roman Catholic in full communion with the Catholic Church and joyfully faithful to the teachings of the Magisterium;

- Views Catholic education as a vocation and understands the Headmaster's role as one of formation as well as administration;

- Possesses a strong understanding of Catholic classical education and the integration of faith and reason;

- Is an excellent educator capable of recognizing excellent teaching and helping other teachers grow;

- Can help recruit, form, inspire, and unite a founding faculty;

- Possesses the confidence to lead and the humility to listen;

- Communicates exceptionally well with students, parents, faculty, Board members, benefactors, clergy, and the broader community;

- Has the initiative, adaptability, energy, and resourcefulness required to launch and grow a new school; and

- Demonstrates a collaborative, mission-first approach to leadership and a willingness to subordinate personal preference to the good of the Academy and its students.

Qualifications
Required
- Bachelor's degree from an accredited college or university;

- Minimum of two years of successful classroom teaching experience in a classical education setting, preferably at the secondary level, sufficient to demonstrate mastery of instruction and the ability to mentor other educators;

- Demonstrated educational leadership ability;

- Strong understanding of Catholic education and classical pedagogy;

- Ability to supervise, mentor, evaluate, and develop educators; and

- Practicing Roman Catholic in full communion with the Catholic Church and committed to the mission of Chesterton Academy.

Strongly Preferred
- Master's degree in education, educational leadership, theology, classical studies, humanities, or a related field;

- Previous school administration or instructional leadership experience;

- Experience in a Catholic classical school;

- Familiarity with the Chesterton Schools Network;

- Experience launching or growing a school or educational organization; and

- Experience with admissions, enrollment, advancement, fundraising, or organizational development.

About Ave Maria
Chesterton Academy of Ave Maria will be located in the growing Catholic community of Ave Maria, Florida, in Southwest Florida.

Ave Maria is also home to Ave Maria University, creating distinctive opportunities for intellectual, educational, spiritual, cultural, and community collaboration as the Academy grows.

Because the Headmaster will be a visible and active leader within the school and broader community, the successful candidate will be required to reside in Ave Maria or within approximately a 30-minute drive of the Academy.

Compensation and Start Date
This is a full-time, year-round position.

Starting salary is $105,000+, negotiable based upon qualifications and experience. Competitive compensation will be commensurate with experience; benefits will be discussed with qualified candidates.

CAAM's preference is for the selected Headmaster to begin as soon as practicable in order to participate fully in faculty recruitment, admissions, advancement, and school-launch preparation. The exact start date will be negotiated between CAAM and the selected candidate.

How to Apply
Qualified candidates should submit to info@chestertonavemaria.com:

Resume or CV;

Cover letter, including a statement of interest and the candidate's philosophy of Catholic classical education; and

Professional references.

Application Deadline: October 9, 2026

Chesterton Academy of Ave Maria seeks a founding leader who sees building a new Catholic classical school not merely as an administrative challenge, but as a mission: forming teachers, serving families, educating young men and women in wisdom and virtue, and helping establish an institution for generations to come.

About the Employer

Under the patronage of G.K. Chesterton and in partnership with families and the Church, the mission of Chesterton Academy of Ave Maria is to partner with parents to educate students in the classical tradition, grounded in the truths of the Catholic faith, and to form them to become joyful leaders prepared to excel in their chosen pursuits, serve their neighbor with humility and in charity, and to foster a Culture of Life, answering God's call to holiness and sainthood.