Benefits:
401(k)
401(k) matching
Competitive salary
Employee discounts
Opportunity for advancement
Training & development
Reports to: Board of Directors
Administrative Model
The Headmaster and the Executive Director lead the administrative team at Chesterton Academy. This model of school administration is one of equality with both specific and shared responsibilities.
The Headmaster is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional personnel, the curriculum, and student life.
The Executive Director is responsible for the business aspects of the administration including finances, human resources, fundraising, strategic planning, public relations, and building facility.
These co-leaders share responsibilities for nurturing and maintaining the mission and traditions of the school, and ensuring fidelity to the Magisterium. Both administrators are hired by and report directly to the Board of Directors.
Summary
The Headmaster serves as the educational leader, responsible for managing the policies, regulations, and procedures to ensure that all students are supervised in a safe, learning environment that adheres to our Catholic identity and meets the approved curricula and mission of the school. The Headmaster is responsible for the curriculum, instructional leadership of the school, hiring and supervision of instructional personnel, student life, discipline and related parent communication.
The Headmaster must be practicing Roman Catholic, possess the minimum of a Master’s Degree in Administration or related field, and demonstrate a commitment to Catholic secondary education. Salary is competitive and commensurate with experience.
The Board of Directors appoints the Headmaster of Chesterton Academy. A collaborative relationship between the Headmaster and Executive director is a requirement. In addition to any teaching responsibilities, the duties of the Headmaster include: (1) curriculum and academic excellence; (2) instruction; (3) student life and discipline; (4) parent communications; (5) student admissions; (6) guidance; (7) other school operations.
Primary Responsibilities and Duties
Curriculum and Academic Excellence
Oversee adherence to Chesterton Schools Network curriculum
Oversee implementation of changes to curriculum
Review results of student tests (CLT, PSAT, ACT, SAT)
Oversee school accreditation process and renewal per Network guidelines
Instruction
Oversee faculty hiring, evaluation, rehires, terminations
Conduct classroom observations for faculty members as part of evaluation process
Student Life and Discipline
Ensure discipline policies are enforced, communicated
Oversee parent-led sports and extracurricular activities
Ensure effectiveness of virtue house and faculty mentor programs
Oversee academic and behavioral eligibility for extra-curricular activities
Parent Communications
Send weekly Headmaster Missive to parents or school newsletter
Meet with parents regarding student discipline and academic issues
Admissions
Admit new students upon review of placement exam, student application materials, and meeting
Oversee transfer student process (curriculum, regulations, forms, financial)
Review placement tests and contact parents with remedial needs
Deliver presentations to prospective parents and students at selected school events
Guidance
Coordinate standardized testing, college applications and transcript preparation
Communicate with colleges, universities and other post-high school programs
Promote various vocational opportunities
Other School Operations
Oversee selection and evaluation of vendors (software, textbooks, other services)
Teaching Responsibilities (as needed)
Relationships
The Headmaster maintains the following working relationships:
The Headmaster reports directly to the Board of Directors.
The Headmaster maintains a consultative, collaborative relationship with the Executive Director.
The Headmaster maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.
Requirements
Education:
Masters in Education or related field
Experience:
Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.
Certification:
Not required
About Chesterton Academy of the Divine Family
Founded in 2025 in responds to a spiritual calling, Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about Chesterton Academy of the Divine Family and the growing national Chesterton Schools Network.