Chesterton Academy of the Holy Hearts (CAHH) is a new, independent classical high school in the Catholic tradition opening 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.

We are seeking a founding headmaster for the school, who is passionate about classical Catholic education. The successful candidate should be a prayerful servant leader who is a capable administrator and nurturing educator with an ability to form the character of young people. As the leader of the school the headmaster must be able to ignite support and enthusiasm for classical education among faculty, parents, and stakeholders.

The headmaster serves as the educational and spiritual leader of the school, responsible for managing the policies, regulations, and procedures to ensure all students are supervised and learning in a safe environment that is rooted in the Catholic faith and adheres to our school’s mission. The headmaster is responsible for working closely with the Founding Board to implement the Founders’ vision while ensuring school policies that foster a rigorous, yet loving, learning environment are followed. The headmaster will be able to offer ideas and best practices in a spirit of collaboration but also be able to accept and follow directives from the Founding Board.

Position Requirements
Must be practicing Catholic and demonstrate a commitment to the teachings of the Catholic Church
Oath to the Magisterium is required
Must have a bachelor’s degree or higher
Must have experience in secondary school education and familiarity with classical education
3+ years teaching experience, preferably classical
Master’s degree in Education Administration or related field or equivalent experience preferred

Needed Skills
Exemplary verbal and written communication skills
Ability to adapt to various challenges
Strong interpersonal skills
Comfortable leading, teaching, and speaking to teens
A vibrant personal prayer life
Solid time-management and organizational skills
Ability to listen and take direction
Prudent managerial abilities
Comfortable public speaking
Ability to support and train teachers in classical methods defined by the Chesterton Schools Network (CSN)

Primary Duties and Responsibilities
Curriculum and Academic Excellence Oversee implementation of and adherence to Chesterton School Network curriculum Review results of student tests (CLT, PSAT, ACT, SAT)
Oversee school accreditation process and renewal per Chesterton Schools Network (CSN) guidelines and instruction
Supervise process for faculty hiring/re-hiring, evaluation, and termination
Conduct classroom observations for faculty members as part of the evaluation process
Participate in headmaster training and mentorship program 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 enforced and communicated
Oversee parent-led sports and extracurricular activities
Ensure effectiveness of virtue houses and faculty mentor programs
Oversee academic and behavioral eligibility for extra-curricular activities
Parent Communications Send weekly “Message from Your Headmaster” to parents or include in school newsletter
Meet with parents regarding student discipline and academic issues

Admissions
Admit new students upon review of placement exam, student application materials, and meeting Oversee transfer student process (curriculum, regulations, forms, financials)
Review placement tests and contact parents concerning any student remediation
Deliver presentations to prospective parents and students at selected school events

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

Teaching Responsibilities
Teach up to two courses initially (subject to change as school grows)

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

Salary is competitive and commensurate with experience.