Founding Headmaster - Classical Catholic High School

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

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.