Founding Headmaster — Catholic Classical School

Chesterton Academy of Notre Dame; Wilmington (DE); Hybrid; USD 90,000 - 130,000; Full time

Job summary

Chesterton Academy of Wilmington seeks a founding Headmaster to lead academic operations and spiritual life as the school opens in Fall 2027. You'll begin before opening to set curriculum, hire faculty, and recruit our first families.

Reporting to the Board of Directors, you will oversee curriculum implementation, faculty mentoring, liturgies, recruitment, communications, and community outreach. This role shapes school culture and governance.

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.

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.

Skills

Faithful Catholic

Strong character

Mentoring and coaching

Communication

Budget planning

Education

Master’s degree or PhD preferred

Job description

Chesterton Academy of Wilmington seeks a founding Headmaster to lead academic operations and spiritual life as the school opens in Fall 2027. You'll begin before opening to set curriculum, hire faculty, and recruit our first families.

Reporting to the Board of Directors, you will oversee curriculum implementation, faculty mentoring, liturgies, recruitment, communications, and community outreach. This role shapes school culture and governance.