Headmaster

Job Description

Headmaster
Chesterton Academy of Wilmington

About the School
Chesterton Academy of Wilmington is a new Catholic, classical school opening in Wilmington, Delaware in the Fall of 2027. We exist to help parents raise up a new generation of joyful leaders and saints, forming young men and women who know and love the truth, and who magnify Jesus Christ, Truth himself, with their lives.

Our students read the Great Books, take advanced math and science, study Latin, explore the fine arts, and grow in a school culture of joy, respect, and deep engagement, all centered on the Eucharist. We follow the Catholic classical liberal arts tradition and the Chesterton Academy model.

Overview
We are looking for a founding Headmaster to lead the academic and spiritual life of the school and to help build it from the start. Because we open in the Fall of 2027, the Headmaster will begin well before that date to establish curriculum, hire faculty, and recruit our first families.
The Headmaster reports to the Board of Directors.

Responsibilities
• Responsible for all academic operations.
• Oversee the implementation of the Catholic classical liberal arts curriculum in the Chesterton Schools Network model.
• Hire the academic staff, supported by the Executive Director and administrative staff on HR matters.
• Mentor and coach faculty for their ongoing development, and develop enrichment opportunities for students and staff.
• Oversee school liturgies (daily Mass, morning and evening prayer, class prayer), encourage students in their spiritual life, and provide opportunities for Confession.
• Play a key role in recruitment, admissions, and enrollment, including student and family interviews.
• Communicate clearly with staff, students, parents, and the wider community (for example, a weekly newsletter and a weekly faculty meeting).
• Implement initiatives for community building and parent formation, and collaborate with the leadership team on community outreach.
• Oversee parent-led sports and extracurricular activities.
• Maintain the program budget in conjunction with the Board of Directors.
• Attend and participate in all board meetings, with a Headmaster's report.
• Maintain compliance with program policies, rules, and regulations.
• Participate in professional networks, including CSN, and support school resource development efforts.

Qualifications
• A faithful Catholic in good standing with the Church, faithful to her teachings and active in the practice of the faith, and willing to sign our statement of faith.
• A love of our Lord Jesus Christ, of children, of the Catholic faith, and of the classical liberal arts tradition.
• A man or woman of strong character, committed to giving a Gospel witness.
• Able to cultivate a beautiful student culture and a joyful discipline.
• A gift for mentoring and coaching faculty.
• Secondary-level teaching experience, with school administrative experience. A master's degree or PhD is preferred.
• A working understanding of budgets, planning, and common school operations (safety, compliance, recordkeeping).
• Timely and effective communication with staff, students, parents, and supporters.
Experience at a classical Christian school, and familiarity with the Chesterton or CSN model, are a plus.

Details
• Location: Wilmington, Delaware
• Opening: Fall 2027
• Start date: End of 2026

To Apply
Please send a cover letter, resume, and three professional references to hello@cawilm.org.

About the Employer

A joyful, classical Catholic high school forming students in Jesus Christ for lives of clarity, purpose, and virtue.