Headmaster

Job Description

Chesterton Academy of the Holy Hearts is seeking an experienced, mission-driven headmaster who is passionate about classical Catholic education. The successful candidate should be a prayerful servant leader, a capable administrator, and a nurturing educator who can foster a school culture where students flourish academically and spiritually. As the educational and spiritual leader of the school, the headmaster is expected to cultivate a strong Catholic identity, lead the staff, and oversee academics and student life. The headmaster must also be able to ignite support and enthusiasm for classical education among faculty, parents, and stakeholders.

CAHH operates as an independent school, led by a Board of Directors. The headmaster reports directly to the Board and is responsible for working closely with the Board to implement the Boards' vision. The headmaster will be able to offer ideas and best practices in a spirit of collaboration but should also be able to accept and follow directives from the Board.

Above all, we are seeking a headmaster to serve as the "teacher of teachers" - a leader who knows excellent teaching firsthand and firmly believes that classical education makes a difference. The headmaster must be able to clearly articulate that vision and form teachers to grow in their vocation and work together as a unified team to help create a flourishing school where everything centers around Christ and the Catholic faith.

Position Requirements:
Must be a practicing Catholic in full communion with the Catholic Church and demonstrate a commitment to the teachings of the Catholic Church

Must have a bachelor's degree; master's degree in educational administrational, or related field, or equivalent experience preferred

Must have a deep knowledge and significant practical teaching experience with classical education, preferably at the secondary level

Must have experience supervising, mentoring, and developing educators

Previous educational administration or instructional leadership experience strongly preferred

Primary Duties and Responsibilities:
*Curriculum and Academic Excellence
-Oversee curriculum and academic excellence, ensuring faithful implementation of the Chesterton Schools Network curriculum and classical Catholic educational philosophy
-Supervise, form, and retain excellent teachers who embrace the mission of Chesterton Academy
-Provide instructional leadership and professional development, helping teachers grow in classical pedagogy, classroom management, discussion, assessment, and student engagement
-Supervise process for faculty hiring/re-hiring, evaluation, and termination
-Conduct classroom observations for faculty members as part of ongoing evaluation and coaching
-Participate in headmaster training and mentorship as outlined by CSN

*Student Life and Discipline
-Implement the St. John Bosco "Preventive Method" as the guiding model of discipline
-Ensure discipline policies are consistently enforced and communicated
-Oversee parent-led sports and extracurricular activities
-Lead the House system and faculty mentorship program
-Oversee academic and behavioral eligibility for extra-curricular activities

*Parent Communication and Formation
-Participate in admissions and prospective-family meetings, helping families understand the school's Catholic and classical educational philosophy
-Send weekly "Message from Your Headmaster" to parents or include in school newsletter
-Communicate effectively with students, parents, and faculty regarding academic, behavioral, and student-life matters
-Provide opportunities for parent formation

*Admissions
-Admit new students upon review of placement exam, student application materials, and family interview
-Oversee transfer student process (curriculum, regulations, forms)
-Review placement tests and contact parents concerning any student remediation needs
-Deliver presentations to prospective parents and students at selected school events
Guidance
-Coordinate standardized testing (CLT, PSAT, ACT, SAT), college applications, and transcript preparation
-Communicate with colleges, universities and other post-secondary programs in order to provide relevant information to students
-Promote various vocational opportunities

*Teaching Responsibilities
-Teach approximately two courses (about 10 periods per week) depending on areas of expertise

Needed Skills:
Be an excellent communicator who can build trust, unity, and collegiality among faculty
Ability to adapt to various challenges and willingness to jump in wherever needed in a small, growing school
Strong interpersonal skills
Comfortable leading, teaching, and speaking to teens
A vibrant personal prayer life
Understand the classical liberal arts tradition, including grammar, logic, rhetoric, Great Books, seminar discussion, and formation of the whole person
Solid time-management and organizational skills
Ability to listen and take direction
Prudent managerial abilities
Comfortable public speaking
Willingness to put the mission of the school ahead of personal preferences or individual agendas
Ability to support and train teachers in classical methods defined by the Chesterton Schools Network (CSN)

Candidates should familiarize themselves with Chesterton Academy of the Holy Hearts and the Chesterton Schools Network via our website.

Salary is competitive and commensurate with experience.

Please forward a cover letter, resume, and three professional references to office@caholyhearts.org.

About the Employer

Chesterton Academy of the Holy Hearts (CAHH) is an independent classical high school in the Catholic tradition that opened in Visalia, California in fall 2026. Inspired by the beauty and richness of the Catholic faith, CAHH seeks to form young men and women to be joyful leaders and saints. By introducing them to great thinkers such as Socrates, Thomas Aquinas, and Dante, and by forming them in a distinctly Catholic culture, we lead students to choose for themselves the adventure of being a disciple of Christ.