Founding Headmaster

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

As the school grows, the role will develop into full academic and administrative leadership.

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.