Headmaster

Job Description

Position:
Headmaster

Reports to:
Board of Directors

Location:
Chesterton Academy of St. Serra, Orinda, California

Start Date:
July 1, 2026 - the Feast of Saint Junipero Serra

Status:
Full-Time, Exempt

Application Deadline:
February 22, 2026 - Feast of the Chair of Saint Peter, Apostle or until position is filled

Submit Application Here:
https://form.jotform.com/260456404641150

Position Summary:
The Headmaster serves as the educational leader of Chesterton Academy of St. Serra. This position is responsible for the instructional life of the academy, ensuring that all students are supervised in a safe, learning environment with policies, regulations, and procedures that adheres to our joyful, Catholic identity while guiding the approved curricula and meeting the mission of the school.

As leader of CASS's mission and curator of our academic community and culture, the Headmaster plays a crucial role in creating a culture of excellence, a vibrant and joyful environment that attracts and retains students and families. The Headmaster serves as the lead teacher, leader of CASS's faculty, and are responsible for guiding our faculty as they provide a learning environment that is faithful to our Catholic identity, the mission of the school, and the Chesterton Schools Network model and curriculum. Additionally, the Headmaster position plays a key role in the formation of teachers as Catholic classical educators and in inspiring enthusiasm for classical Catholic education in general and for Chesterton Academy of the St. Serra in particular among all stakeholders in our community.

This role requires a leader who is:
A practicing Roman Catholic with a strong prayer life;
A joyful disciple of Jesus Christ with deep commitment to the Magisterium;
A skilled educator who loves teaching Catholic Secondary Classical Education and forming teenage students;
A collaborative partner within a dual-leadership model alongside the Executive Director;
A resourceful, innovative, and solution-oriented approach to leadership with superior organizational skills and attention to detail;
& a mission-driven leader with a startup mindset, marked by comfort in fast-paced and evolving environments; willingness to take ownership; ability to create systems and processes; and skill in inspiring faculty and staff to have the same dedication and mindset;

The responsibilities of the Headmaster include:
Curriculum & Academic Excellence, Instruction & Faculty Excellence, Student Life & Discipline, Parent Relationships & Communications, Admissions & Long-Term Student Success, Other School Operations & Teaching Responsibilities (as needed), and Mission Integration.

Further details on responsibilities of the Headmaster are included in the "Primary Responsibilities and Duties" section below.

Primary Responsibilities and Duties:

1) Curriculum & Academic Excellence
Oversee adherence to Chesterton Schools Network curriculum
Oversee implementation of tailored additions to curriculum or extracurricular programs created to meet or exceed the standards of excellence set by the board
Support Executive Director in nurturing and leveraging key partnerships with universities, research institutions, and corporations to enhance CASS academics and expand CASS students internship program
Lead faculty in courses' review process to facilitate class AP eligibility and A-G requirements, and college credit
Review results of student tests (CLT, PSAT, ACT, SAT)
Oversee school accreditation process and renewal per Network guidelines
Working with the academic Dean apply for A to G approval from the University of California at Berkeley for Chesterton courses.

2) Instruction & Faculty Excellence
Oversee faculty hiring, evaluation, rehires, terminations
Conduct classroom observations for faculty members as part of evaluation process
Coach, mentor and supervise faculty members and provide ongoing
staff development programs as appropriate.
Leverage new or existing partnerships with universities or community colleges to offer college level classes

3) Student Life & Discipline
Ensure discipline policies are enforced, communicated
Oversee parent-led sports and extracurricular activities
Identify selected programs or competitions for students to showcase their skills and talents
Ensure effectiveness of CASS house system
In coordination with the Athletic Director, oversee academic and behavioral eligibility for extra-curricular activities
Organize academic and school calendar, including faculty and students retreats, activities supporting the Cultura Vitae mission, pilgrimages, and annual pilgrimage to Rome

4) Parent Relationships & Communications
Send weekly Headmaster Missive to parents or school newsletter
Meet with parents regarding student discipline and academic issues

5) Admissions & Long-Term Student Success
Admit new students upon review of placement exam, student application materials, and meeting
Oversee transfer student process (curriculum, regulations, forms, financial)
Deliver presentations to prospective parents and students at selected school events in the community
In coordination with the Academic Dean, coordinate standardized testing, college applications and transcript preparation
Communicate with colleges, universities and other post-high school programs

6) Other School Operations & Teaching Responsibilities (as needed)
Oversee selection and evaluation of vendors (software, textbooks, other services)
Support Executive Director with fundraising efforts and with community outreach, to retain students and grow enrollment
Teaches up to 2 courses in addition to other Headmaster duties (As needed)

7) Mission Integration
Maintain/establish and implement, in collaboration with the Executive Director, faculty and staff, policies and programs designed to integrate the philosophy and mission of the school founders.
Ensure all internal-facing operations, advancement efforts, and communications are faithful to the mission, vision, and Chesterton Schools Network model.
Support a culture of joy, mission-focus, and classical Catholic education throughout the school community.

Relationships:
The Headmaster maintains the following working relationships:
The Headmaster reports directly to the Board of Directors.
The Headmaster maintains a consultative, collaborative relationship with the Executive Director.
The Headmaster maintains a supervisory relationship with faculty and other selected staff.
Builds relationships with students, parents, parishes, and other community stakeholders.
Is involved with fund raising opportunities and nurtures relationships with donors.

Administrative Model:
The Headmaster and Executive Director lead CASS together in an administrative model of shared responsibility and mutual respect and serve as ambassadors upholding the Catholic mission of the school. The Headmaster oversees internal school operations, while the Executive Director oversees external operations.
The Headmaster is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional personnel, the curriculum, and student life. The Executive Director is responsible for the business aspects of the administration including finances, human resources, fundraising, strategic planning, public relations, and building facility.
These co-leaders share responsibilities for nurturing and maintaining the mission and traditions of the school, and ensuring fidelity to the Magisterium. Both administrators are hired by and report directly to the Board of Directors.

Position Requirements:
The Headmaster must be a practicing Roman Catholic, demonstrate a commitment to advancing the mission of classical Catholic secondary education, and must be willing to take an Oath of Fidelity to the Magisterium of the Catholic Church.

Education:
Masters in Education, Administration, Educational Leadership or related field (Recommended)

Experience:
Significant teaching experience in a classical Catholic school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.

Certification:
Not required

Compensation:
Salary is competitive and commensurate with experience.

Application Process

Applicants should submit the following in their application:
1) Cover letter describing interest and alignment with the mission
2) Curriculum vitae
3) Three professional references (names, relationship, phone, email)
4) One pastoral reference (name, relationship, phone, email)
5) Video (Instructions in Application Form)

Applications are due by February 22, 2026 or until the position is filled.

About Chesterton Academy of St. Serra (CASS):
Chesterton Academy of St. Serra is a joyful, new, independent classical high school in the Catholic tradition, rooted in the teachings of the Church and the model of the Chesterton Schools Network.

About the Chesterton Academy Network:
Founded in 2008 as a result of a grass-roots movement of parents, Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of 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. Learn more about Chesterton Academy and the growing national Chesterton Schools Network.

Submit Application Here: https://form.jotform.com/260456404641150

About the Employer:
The mission of Chesterton Academy is to help parents raise a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. Our rigorous, integrated curriculum unlocks student potential and prepares students to succeed in college and professional life, and to excel in service of family, country, and Christ our Lord.

About the Employer

The mission of Chesterton Academy is to help parents raise a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. Our rigorous, integrated curriculum unlocks student potential and prepares students to succeed in college and professional life, and to excel in service of family, country, and Christ our Lord.