Founding Headmaster — Classical Catholic High School

Chesterton Academy of Notre Dame; Winston-Salem (NC); Hybrid; USD 110,000 - 170,000; Full time

Job summary

Chesterton Academy of Winston-Salem seeks a founding Headmaster to lead the educational program rooted in Catholic tradition. The role includes curriculum oversight, faculty hiring and evaluation, student life, discipline, parent communication, and admissions oversight.

Reporting to the Board of Directors and collaborating with the Executive Director, the Headmaster will shape the school culture, ensure alignment with Chesterton Network curricula, and drive academic excellence for Fall 2027

Qualifications

• Bachelor level degree required; master's preferred.
• Significant teaching experience in a classical school environment preferred; secondary school admin experience ideal.

Responsibilities

• Oversee curriculum and academic excellence aligned with Chesterton Schools Network.
• Lead hiring, supervision, and evaluation of instructional staff.
• Manage student life, discipline, and parent communications.
• Oversee admissions, guidance, and student support services.
• Coordinate with executive leadership and board on policy and strategic direction.
• Manage school operations, vendor selections, and program implementation.

Skills

Leadership

Curriculum oversight

Communication

Catholic identity

Education

Undergraduate degree

Masters in Education or related field preferred

Job description

Chesterton Academy of Winston-Salem seeks a founding Headmaster to lead the educational program rooted in Catholic tradition. The role includes curriculum oversight, faculty hiring and evaluation, student life, discipline, parent communication, and admissions oversight.

Reporting to the Board of Directors and collaborating with the Executive Director, the Headmaster will shape the school culture, ensure alignment with Chesterton Network curricula, and drive academic excellence for Fall 2027