Headmaster

Job Description

Position: Founding Headmaster
Chesterton Academy of Vero Beach

Chesterton Academy of Vero Beach (CAVB), a classical high school in the Catholic tradition opening in Vero Beach, FL in the fall of 2025, is seeking its founding 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 (CSN) 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 a Practicing Roman Catholic with a Working Understanding of the Teachings of the Catholic Church
• Possess a Master's Degree in Administration or Related Field
• Have Teaching Experience in a Classical School Environment
• Have Experience in School Administration
• Be familiar with the Mission of CAVB and the CSN
• Have a Joyful Persona

In addition to any teaching responsibilities, the duties of the headmaster include, but are not limited to:

• Student/Family Communication, Interviews, Admission, and Formation
• Understanding, Protecting, and Implementing the CSN Curriculum
• Faculty and Staff Hiring, Instruction, and Oversight
• Advising and Assisting the Board in Starting the School
• Creating and Fostering a Joyful Culture
• School Administration
• Community Building
• Other School Operations

A complete job description can be found at the address below.
https://chestertonvero.org/news/were-hiring

Interested applicants must provide a curriculum vitae, three references (one from a member of religious life), and a brief paragraph outlining your interest in this position.

Please send all applications and inquiries to Daniel Whalen via chestertonvero@gmail.com.

Salary is competitive and commensurate with experience.

About the Employer

Chesterton Academy of Vero Beach is a classical high school in the Catholic tradition located in the Vero Beach area offering an integrated, rigorous curriculum centered on Jesus Christ. 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.