Headmaster

Chesterton Academy of Winston-Salem; Winston-Salem (NC); On-site; USD 90,000 - 130,000; Full time

Job summary

Chesterton Academy of Winston-Salem is seeking a founding headmaster to guide the school’s development, culture, and Catholic identity. You will lead curriculum, instruction, student life, discipline, and communications while partnering with the Board of Directors.

The role emphasizes curriculum fidelity, hiring and supervising staff, and building a culture of faith and academic excellence for Fall 2027. Starts in Jan 2027; strong leadership required.

Qualifications

• Undergraduate degree; Masters in Education or related field preferred.
• Significant teaching experience in a classical school environment.
• Experience in secondary school administration ideal.
• Familiarity with Chesterton Academy mission and Catholic Church teachings.
• Working knowledge of institutional advancement/fundraising.
• Certification not required.

Responsibilities

• 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 management.
• Parent communications and weekly updates.
• Admissions oversight and presentations to prospective families.
• Guidance on college applications and post-high school planning.
• Oversee school operations and vendor selections.

Skills

Leadership

Curriculum oversight

Faculty evaluation

Strategic planning

Education

Undergraduate degree

Masters in Education or related field

Job description

ABOUT THE SCHOOL Chesterton Academy of Winston-Salem, opening Fall of 2027, is a classical high school rooted in Catholic Tradition that seeks to raise a generation of saints. 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. We are seeking a founding headmaster to help build this culture of hope focused on the intellectual and spiritual formation of students using the Chesterton Schools Network curriculum. 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