Executive Director

Job Description

Position:
Executive Director

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 Executive Director serves as the business, operational, and advancement leader of Chesterton Academy of St. Serra. This position is responsible for the external life of the academy, ensuring that CASS operates with excellence in finance, fundraising, operations, human resources, facilities, enrollment, marketing, and strategic planning-all in fidelity to CASS's joyful Catholic mission.

As co-leader of CASS's mission and steward of the school's growth and sustainability, the Executive Director plays a defining role in shaping the long-term trajectory of CASS and ensuring its ability to form a new generation of joyful leaders and saints. The Executive Director oversees advancement operations, builds strong relationships with benefactors, donors, parishes, and the broader community, and ensures communications, public relations, and enrollment efforts support the school's mission and identity.

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 seasoned administrator with expertise in financial management, strategic planning, and organizational leadership;
-A collaborative partner within a dual-leadership model alongside the Headmaster;
-Mission-driven and entrepreneurial, comfortable in a startup-like environment, capable of creating systems and structures from the ground up;
-A skilled communicator and relationship-builder with the ability to inspire confidence among parents, donors, Board members, parishes, and the wider community;
-& committed to ensuring all operations, communications, and advancement activities reflect the Catholic classical mission of CASS.

The Executive Director must possess strong leadership skills that inspire excellence and cooperation from all constituent groups and demonstrate positive convictions about Chesterton's unique integrated curriculum and dedication to building a culture of life, comprehensive working knowledge of school finance, operations, and budgeting, the ability to promote a strong institutional advancement (fundraising) program, and a commitment to continuing and enhancing strategic planning. Familiarity with public relations and communications and the supervision of facilities will be valuable assets.

The responsibilities of the Executive Director include: (1) Institutional Advancement & Fundraising, (2) Finance & Operational Excellence, (3) Strategic Planning and Board Collaboration, (4) Marketing, Enrollment & External Relations, & (5) Mission Integration.

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

Primary Responsibilities and Duties:

(1) Institutional Advancement & Fundraising
-Lead all advancement efforts to meet and exceed annual fundraising goals
-Develop and execute long-term advancement and capital strategies to support school sustainability and growth
-Build and maintain strong relationships with benefactors, prospective donors, parishes, and community partners
-Oversee donor communications, events, and stewardship

(2) Finance & Operational Excellence
-Oversee all financial operations, including budgeting, long-term financial planning, and reporting to the Board
-Ensure best practices in accounting, compliance, and internal controls
-Supervise human resources, payroll, and personnel policies
-In collaboration with the Headmaster, direct facilities management, vendor selection, contracts, and campus needs

(3) Strategic Planning and Board Collaboration
-Collaborate with the Board of Directors to advance the long-term mission, vision, and sustainability of CASS
-Provide timely financial and operational reports, recommendations, and analysis to the Board.
Implement Board policies and directives

(4) Marketing, Enrollment & External Relations
-Oversee communications and public relations to ensure the school is positively represented and its mission is clearly articulated
-Support admissions and enrollment initiatives, fostering relationships with prospective families, feeder schools, and parish communities
-Promote CASS within the broader community, ensuring alignment with its joyful Catholic classical identity
-Strengthen parent, community, and parish engagement to cultivate a thriving school ecosystem

(5) Mission Integration
-Maintain/establish and implement, in collaboration with the Headmaster, faculty and staff, policies and programs designed to integrate the philosophy and mission of the school founders.
-Promote a culture of excellence by developing, nurturing, and leveraging key partnerships that can enhance academics, student life, or other aspects of a CASS education.
-Ensure all external-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 Executive Director maintains the following working relationships
-The Executive Director reports directly to the Board of Directors.
-The Executive Director maintains a consultative, collaborative relationship with the Headmaster.
-The Executive Director maintains a supervisory relationship with selected staff.
-Builds relationships with parents, donors, parishes, and other community stakeholders.

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 Executive Director 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 Administration, Business or related field (recommended)

Experience:
Demonstrated success in administration, nonprofit leadership, or school operations; Experience in finance, budgeting, and strategic planning; Experience in institutional advancement/fundraising and donor stewardship; Experience in marketing, enrollment, and public relations; Secondary school administrative experience preferred; Familiarity with Chesterton Academy's mission and the teachings of the Catholic Church.

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) Resume or Curriculum Vitae
3) Three professional references (names, relationship, phone, email)
4) One pastoral reference (name, relationship, phone, email)
5) Video (Instructions included 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.