Chesterton Academy of Orlando
February 1, 2022
2025 State Road 436, Winter Park, FL 32792, Orlando, Florida
Job Type


Chesterton Academy of Orlando, a new classical high school rooted in the Catholic faith, seeks a talented and dynamic full-time Headmaster to lead the launch of its school opening in the 2022-23 academic year. This is a rare opportunity for one called to leadership in Catholic, classical education.

The Headmaster serves as the educational and organizational leader and is responsible for implementing the curriculum, managing the teaching staff, and maintaining a strong culture of joy and virtue at the school. He or she is responsible for instructional leadership (teacher growth and development), curriculum oversight, hiring and supervision of personnel, student life, discipline, and all parent communications.

The Headmaster will ensure that students are in a learning environment that develops both faith and reason, allows them to discover their God-given talents, and discern their ultimate calling with joy.

Responsibilities include:

• Admit new students upon review of placement exam, student application materials, and meeting
• Oversee transfer student process (curriculum, regulations, forms, financial)
• Review placement tests and contact parents with remedial needs
• Deliver presentations to prospective parents and students at selected school events

Curriculum and Academic Excellence
• Oversee adherence to and any changes to the curriculum
• Collect course materials for each class (syllabus, weekly teaching plan, tests)
• Review results of student tests (CLT8) and make stipulations regarding course content and delivery as needed
• Oversee school accreditation process and renewal

• Oversee faculty hiring, evaluation, rehires, and terminations
• Conduct classroom observations for faculty members as part of evaluation process

Student Life and Discipline
• Ensure discipline policies are communicated and enforced
• Oversee extracurricular activities and help with parent-led sports
• Ensure effectiveness of House System and faculty mentor programs
• Oversee academic and behavioral eligibility for extra-curricular activities

Parent Communications
• Send weekly Headmaster Missive to parents
• Meet with parents regarding student discipline and academic issues

• Coordinate standardized testing, college applications, and transcript preparation
• Communicate with colleges, universities, and other post-high school programs
• Promote various vocational opportunities

Other School Operations
• Oversee selection and evaluation of vendors (software, textbooks, other services)

Teaching Responsibilities (as needed)
• We would prefer a candidate who can teach at least 1-2 courses, such as Theology, Philosophy, Latin, History, Math, Science, or other disciplines.

• Masters Degree in Education or related field
• Significant teaching experience in a classical school environment
• Previous experience in secondary school administration
• Familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church
• Working knowledge of institutional advancement/fundraising

About Chesterton Academy of Orlando
Founded through a grass-roots movement of parents, Chesterton Academy of Orlando offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. A member of the Chesterton Schools Network, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about the school at

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