Headmaster

Chesterton Academy of Vero Beach, a classical high school in the Catholic tradition in Vero Beach, FL established in 2025, is seeking a headmaster.

As headmaster and educational leader of CAVB, you will be responsible for implementing the school's academic vision and mission, upholding the school's discipline policies and traditions (including adhering to the Chesterton Schools Network curriculum), and also the hiring, mentoring, and training of teachers. The headmaster will work in collaboration with the executive director and the executive team, which is responsible for the image, public relations, fundraising, enrollment/tuition, activities, events, recruiting, and marketing of the school, and should provide support in these activities.

Working with the Executive team on building strong parent-school relationships and communication is also included. A collaborative relationship between the headmaster, the executive director, and the board is a requirement and essential to the success of the school.

The headmaster must be practicing Roman Catholic and possess a passion for Catholic, classical secondary education. Other requirements include teaching experience in a classical school environment, preferably Catholic; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy of Vero Beach, the Chesterton Schools Network, and the teachings of the Catholic Church; and the minimum of a Master’s Degree or equivalent experience.

• Adhering to and Protecting the Curriculum to Ensure Academic Excellence
• Creating and Fostering a Joyful Culture
• Faculty and Staff Hiring, Instruction, and Oversight
• Student Life and Discipline
• Parent Communications
• Student Admissions
• Community Building
• School Administration
• Promoting the School
• Other School Operations

For a complete job description please visit (Use the "Apply for this Job" box below).-

• A cover letter outlining your interest in this position
• A curriculum vitae
• Three (3) professional references
• One (1) pastoral reference

Please send all applications and inquiries to Dr. Daniel Whalen via careers. Applications received by February 23rd, 2026 will be given priority consideration. The position remains open until filled.

Salary is competitive and commensurate with experience.

Start Date:

July 1, 2026