Careers at Chesterton

Headmaster

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, ideally 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
• Oversee faculty hiring, evaluation, rehires, terminations
• Conduct classroom observations for faculty members
Student Life and Discipline
• Ensure discipline policies are enforced, communicated
• Oversee parent-led sports and extracurricular activities
• Ensure effectiveness of virtue house and faculty programs
• Oversee academic and behavioral eligibility for extra activities
Parent Communications
• Send weekly Headmaster Missive to parents/school newsletter
• Meet with parents regarding student discipline and academics
Admissions
• Admit students (placement exam, application, and meeting)
• Oversee transfer student process
• Review placement tests and contact parents
• Deliver presentations to prospective parents and students
Guidance
• Organize standardized testing, college applications, transcripts
• Communicate-colleges/universities/post-high school programs
• Promote various vocational opportunities
Other School Operations
• Oversee selection of vendors (software, textbooks, etc.)
• Teaching Responsibilities (as needed)

The Headmaster maintains the following working relationships:
• The Headmaster reports directly to the Board of Directors.
• Maintains a collaborative relationship with Executive Director.
• Maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.

REQUIREMENTS
Education: Undergraduate degree (Masters in Education or related field preferred)
Experience: Significant teaching experience in a classical school environment preferred; previous experience in secondary school administration ideal; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.
Certification: Not required

DETAILS
• Location: Winston-Salem, NC
• Opening: Fall 2027
• Start date: Jan 2027

TO APPLY
Please send a cover letter, resume, and three professional references to chestertonacademywsnc@gmail.com