Headmaster

Terms: Full-Time Employee
Experience: 2-5 Years
Education: Undergraduate Degree
Base Pay: Salary

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.

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

How to apply: https://www.catholicjobs.com/job/16445177317

• 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