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 Administrator to lead academic and student life for the 2025–2026 school year and beyond.

The Administrator 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 administrator ensures that all students are formed in both intellect and virtue within a faithful Catholic culture rooted in the classical tradition.

Responsibilities

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

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

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

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

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