Job Openings
Headmaster | Full-time
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. 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.
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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)
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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, when applicable
• The Headmaster maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.
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Requirements
Education:
Master's in Education or related field
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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.
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Certification:
Not required
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Interested candidates should submit a cover letter, resume, and three references to chair@chestertonacademyofrochester.org.
High School Humanities Teacher | Full-time
Chesterton Academy of Rochester, a joyfully Catholic, classical high school, seeks talented and dynamic full-time Humanities teachers to join our team starting in the 2026-2027 academic year. Part-time positions may also be available.
The successful candidate will be able to teach multiple levels of at least one of the following subjects: History, Latin, Literature, and Theology. A bachelor’s or master’s degree in History, Literature, or a related Humanities or Liberal Arts field is required. Teaching experience is preferred, as well as experience in and passion for Catholic classical education.
The candidate must be a practicing Catholic and willing to take the Oath of Fidelity to the Magisterium. Candidates must demonstrate excellent organizational, written, and verbal communication skills, and possess a track record of contributing to the vision and mission of an apostolic and educational enterprise.
In addition to their teaching responsibilities, faculty at Chesterton Academy participate in the House system, which is designed to promote character and virtue and to help students grow in holiness. Full-time faculty members are required to attend daily Mass with the entire student body and assist in leading and participating in spiritual retreats and school activities.
Interested candidates should submit a cover letter, resume, and three references to dklosterman@chestertonacademyofrochester.org.
About Chesterton Academy of Rochester
Founded in 2014 as a result of a grass-roots movement of parents, Chesterton Academy of Rochester has a small student population and is looking to grow. It offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. As a member of the Chesterton Schools Network, the school develops complete thinkers who learn to draw on faith and reason in order to build a culture of life.
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