Head of School

Job Description

Headmaster
Reports to: 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 a practicing Roman Catholic, possess the minimum of a Master's Degree in Education Administration or related field or equivalent experience, 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. 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 implementation of and adherence to Chesterton Schools Network curriculum
• Oversee implementation of any changes to the 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 and terminations
• Conduct classroom observations for faculty members as part of the evaluation process

Student Life and Discipline
• Ensure discipline policies are enforced and 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 include in 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, financials)
• Review placement tests and contact parents concerning any student remediation
• 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 vendor products (software, textbooks, etc.)

Teaching Responsibilities
• Fill in as needed

Working Relationships
The Headmaster maintains the following working relationships:

• The Headmaster reports directly to the Board of Directors.
• The Headmaster maintains a supervisory relationship with faculty and other selected staff.

Requirements

Education:
Masters in Education Administration or related field or equivalent experience

Experience:
Significant teaching experience in a classical school environment Is preferred; 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
Founded in 2008 as a result of a grass-roots movement of parents, 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 (www.chestertonic.org) and the growing national Chesterton Schools Network (https://chestertonschoolsnetwork.org/).

About the Employer

We are a joyfully, Catholic classical high school raising up the next generation of leaders and saints by forming their intellect, character, and spirituality. We are opening our school August 2026.