Founding Headmaster

Job Description

Chesterton Academy of The Divine Mercy, a new classical Catholic high school, is seeking a Founding Headmaster to help launch and lead the school.

This role is ideal for a faithful Catholic leader who is passionate about Classical education and ready to help build a school from the ground up. Early responsibilities will focus on student recruitment, faculty hiring, and establishing school culture, with the role growing into full academic and administrative leadership.

Responsibilities:
In the school's early phase (pre-opening and Year 1), the Headmaster will focus heavily on:
Student recruitment and family engagement
Faculty recruitment and formation
Building school culture and community identity
Operational setup and early systems creation

The role will develop into full academic and administrative leadership as the school grows.

The Headmaster will:
Serve as the primary ambassador of the school's mission to prospective families and the broader community
Lead and form faculty in the Chesterton Schools Network model of classical Catholic education
Foster a joyful, faithful, and intellectually vibrant school culture
Oversee curriculum implementation, ensuring fidelity to the Catholic intellectual tradition
Teach (typically 2-4 courses) as part of the faculty
Collaborate closely with the Board in strategic planning, enrollment growth, and long-term sustainability

Qualifications
Practicing Roman Catholic (willing to take Oath of Fidelity)
Master's degree required
Teaching experience required (classical preferred)
Leadership experience preferred
Strong communication and organizational skills

Candidate Profile
A strong commitment to the Catholic faith, actively practiced and lived each day
Belief in the value of Catholic classical education
Takes initiative and follows through
Communicates clearly and effectively
Leads with clarity, confidence, and an encouraging spirit

To Apply
Please submit:
Cover letter addressing your interest in founding leadership and Catholic classical education
Curriculum vitae
Three professional references
One pastoral reference

Please direct all inquiries to Jesse Mayhew, Board President, at careers@chestertondm.org

Compensation
Salary is commensurate with experience and reflects the startup nature of the school, with growth as enrollment increases.

About the Employer

Under the patronage of G.K. Chesterton and in partnership with families and the Church, the mission of the Chesterton Schools Network 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.