Head Teacher - High School
Full Time • Hagerstown
Benefits:
- 401(k) matching
- Competitive salary
- Dental insurance
- Health insurance
- Opportunity for advancement
- Paid time off
- Training & development
- Vision insurance
Benefits/Perks
- Daily Mass and spiritual enrichment
- Vibrant, mission-driven faculty and parent community
- Competitive salary (commensurate with experience)
- Professional development through the Chesterton Schools Network
- Opportunity to shape the spiritual, academic, and cultural foundation of a new Catholic high school
Job Summary
Chesterton Academy of The Divine Family, a joyfully Catholic, classical high school in the Chesterton Schools Network, seeks a mission-driven and experienced Head Teacher to lead academic and student life for the 2025–2026 school year and beyond.
The Head Teacher serves as the educational and spiritual leader of the school, responsible for the academic excellence, faculty mentorship, student formation, and the daily rhythm of life at the school. The Head Teacher ensures that all students are formed in both intellect and virtue within a faithful Catholic culture rooted in the classical tradition.
Responsibilities
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Academic Leadership
- Ensure fidelity to the integrated Chesterton Schools Network curriculum
- Oversee faculty development, classroom observations, and academic support
- Coordinate school-wide assessments (CLT, PSAT, SAT, ACT) and student testing schedules
- Support curriculum implementation and continuous academic improvement
- Monitor student progress and support individual growth and remediation plans
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Faculty Oversight
- Lead the hiring, supervision, and evaluation of teaching staff
- Promote a collaborative, mission-focused faculty culture
- Provide mentorship and ongoing formation to new and returning teachers
- Organize and lead professional development in classical pedagogy and Catholic formation
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Student Life & Formation
- Oversee discipline with charity and consistency, grounded in the teachings of the Church
- Supervise virtue-based programs such as the House system and school-wide retreats
- Guide students in character formation, spiritual development, and vocational discernment
- Coordinate extracurricular, academic, and spiritual activities with faculty and staff
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Parent & Community Communication
- Maintain clear, timely, and mission-aligned communication with parents and families
- Support parent-teacher collaboration in academic and disciplinary matters
- Represent the school with joy and integrity in the broader Catholic and classical community
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Admissions & Operations (in collaboration with Executive Director)
- Participate in admissions interviews and placement testing
- Help ensure fidelity to Catholic identity in marketing and messaging
- Assist with academic planning, class schedules, and student placement
Qualifications
- Master’s degree in Education, Administration, or a related field (preferred)
- 5+ years of experience in teaching or leading within a classical or Catholic school
- Deep understanding of Catholic intellectual tradition and classical education
- Practicing Roman Catholic, joyfully faithful to the Magisterium, and willing to take the Oath of Fidelity
- Strong leadership, communication, and interpersonal skills
- A heart for evangelization, mentorship, and forming the next generation of saints and leaders
Compensation: $55,000.00 - $62,290.00 per year
Chesterton Academy of The Divine Family offers a classical, integrated high school education rooted in the Catholic intellectual and spiritual tradition. As part of the Chesterton Schools Network, our mission is to form a new generation of joyful leaders and saints through a curriculum centered on truth, beauty, and goodness. With daily Mass, strong academics, and a vibrant community life, we help students discover their vocation and grow in virtue. Our affordable tuition model ensures that families of all backgrounds can access this transformative education.
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