Join Our Team!

G.K. Chesterton’s joy was never a retreat from the challenges of the age; it was the fruit of moral courage exercised in the face of them. He courageously countered the errors of materialism, relativism, and the erosion of human dignity, not by withdrawing but by speaking clearly and charitably and living faithfully as a disciple of Christ. In the same way, founding a Chesterton Academy is a response to the call to be a light to the nations and to build up the Kingdom of God.

Become a Founder! Our school founders are meeting the urgent formation needs of young people today and growing our local community to foster personal holiness and sanctify the world.

Chesterton Academy of The Divine Mercy is currently seeking a Founding Headmaster.

Start Date: Summer 2026 

Chesterton Academy of The Divine Mercy, a new classical Catholic high school in the Diocese of Springfield, is seeking a mission-driven Catholic leader to serve as its Founding Headmaster.

This is a rare opportunity to help build a school from the ground up - shaping its culture, forming its faculty, and leading its growth from the earliest stages. The ideal candidate is a mission-driven leader with a passion for Catholic classical education, an entrepreneurial spirit, and the ability to inspire families and students to embrace a bold vision for education.

Headmaster’s Role - The Founding Headmaster serves as the chief architect and guardian of the school’s mission, responsible for bringing the vision of Chesterton Academy of The Divine Mercy to life.

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

Characteristics of the Ideal Candidate

  • Strong commitment to Catholic classical education and the formation of young people

  • A faithful Catholic who actively practices and lives out the faith on a daily basis

  • Entrepreneurial mindset: comfortable building, adapting, and leading in a startup environment

  • Ability to attract, inspire, and retain families, students, and faculty

  • Strong communication and public speaking skills

  • A positive and steady leader who communicates clearly and leads with conviction

  • Capacity to build systems, not just operate within them

  • Desire for personal intellectual and spiritual growth

Qualifications

  • Practicing Roman Catholic willing to take the Oath of Fidelity to the Magisterium

  • Master’s degree (required)

  • Teaching experience (classical experience preferred)

  • Leadership experience in education or a mission-driven organization (preferred, but not strictly required for exceptional candidates)

  • Ability to clearly articulate and defend the mission of Catholic education

  • Experience in recruitment, fundraising, or organizational leadership is a strong plus

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 Chesterton Academy of The Divine Mercy

Chesterton Academy of The Divine Mercy is a member school of the Chesterton Schools Network. In partnership with parents, we seek to form joyful leaders and saints through a rigorous classical curriculum grounded in the Catholic intellectual tradition. We aim to cultivate wisdom and virtue by guiding students in the pursuit of Truth, Goodness, and Beauty.