Headmaster

Headmaster
Chesterton Academy of The Florida Martyrs | Pensacola, Florida

About the School
Chesterton Academy of The Florida Martyrs (CAFM) is an independent classical high school, joyfully grounded in the Catholic Faith. Founded in 2023 and located at St. Anne Catholic Parish in Pensacola, CAFM is one of more than 80 member schools in the Chesterton Schools Network, an initiative of the Society of Gilbert Keith Chesterton. The 2026-27 school year is our fourth year of operation, with 26 students and 10 staff (4 full-time), and we project 32 students for 2027-28. The Chesterton model includes an integrated classical curriculum, daily Mass, a house system, clubs, fine arts, and athletics. CAFM accepts Florida’s Step Up for Students scholarship.

Our Mission
Under the patronage of G.K. Chesterton and in partnership with families and the Church, the mission of Chesterton Academy of The Florida Martyrs is to foster a Culture of Life by forming a new generation of joyful leaders and saints, educated in the classical tradition and grounded in the truths of the Catholic Faith.

The Role
We seek a headmaster who shares our heart for a timeless and proven educational model, and who will foster a distinctly Catholic culture in which the Mystery of the Incarnation is infused in every academic subject and aspect of school life. School culture begins with faculty culture, so the headmaster leads a faculty prepared to serve each day as joyful witnesses to Christ. The headmaster serves as the school’s educational leader and provides institutional stability through oversight of both school and business operations. The headmaster is supported by an Advancement Director, who oversees fundraising and development, and an Operations Assistant, and reports to the Board of Directors.

Key Responsibilities

Curriculum and Academic Excellence

Oversee adherence to the Chesterton Schools Network curriculum and the implementation of curriculum changes
Review student test results (CLT, PSAT, ACT, SAT)
Oversee the school accreditation process and renewal per Network guidelines

Instruction

Oversee faculty hiring, evaluation, rehires, and terminations
Conduct classroom observations as part of the evaluation process
Teach one or two classes per semester (if able), leading by example in classical instruction

Student Life and Discipline

Ensure discipline policies are communicated and enforced
Oversee parent-led sports and extracurricular activities, including academic and behavioral eligibility
Ensure the effectiveness of the house system and faculty mentor programs

Parent Communications

Send a weekly Headmaster Missive or school newsletter to parents
Meet with parents about student discipline and academic issues

Admissions

Admit new students after review of the placement exam, application, and family interview
Manage the transfer process, including curriculum adjustments and student transition
Review placement tests and contact parents about remediation needs
Present to prospective families and at selected school events

Guidance

Coordinate standardized testing, college applications, and transcript preparation
Communicate with colleges, universities, and other post-secondary programs
Promote vocational opportunities

Compliance and Operations

Oversee compliance with Step Up for Students, the Florida Department of Education, and other relevant government entities
Coordinate materials acquisition (software, textbooks, furniture, etc.)
Provide financial oversight, including budget drafting and spending oversight, and serve on the Finance Committee

Qualifications

Practicing Roman Catholic
Bachelor’s degree required and willingness to work toward a master’s; a master’s in education or a related field is preferred
Previous experience in secondary education
Familiarity with and commitment to the classical model of education
Familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church
Working knowledge of institutional growth
Significant experience in secondary school administration and/or business administration preferred
Certification is not required, but candidates should be willing to pursue continuing education, including Florida’s Classical Education Teaching Certificate

Compensation: Competitive and commensurate with experience
Start Date: By June 1, 2027. An earlier start is welcome to allow for a transition.
Reports To: Board of Directors

About Pensacola
Pensacola, America’s first settlement (est. 1559), offers more than 50 miles of coastline, a temperate climate, a welcoming community, many vibrant Catholic parishes, and strong school choice policy. In 2025, ConsumerAffairs ranked it the #1 best coastal city to move to.

To Apply
Send the following to csalamida@chestertonpensacola.org with the subject line “Headmaster Position”:

Resume
Cover letter
Statement of Catholic educational leadership philosophy
List of five professional references

Applications are not complete until all requested items are received. All applications are handled with the utmost confidentiality, and references will not be contacted without the candidate’s prior knowledge. Applications are accepted on a rolling basis until the position is filled.Send applications or inquiries to: headmaster@chestertonpensacola.org

About the Employer
Under the patronage of G.K. Chesterton and in partnership with families and the Church, the mission of Chesterton Academy of The Florida Martyrs is to foster a Culture of Life by forming a new generation of joyful leaders and saints, educated in the classical tradition and grounded in the truths of the Catholic faith.