Headmaster

Job Description

(This is an abbreviated job description. The full job description will be given to all applicants.)

Position: Headmaster
Job Period: 2026-27 Academic Year, July 1, 2026-June 30, 2027
Grade Levels: TK-8
Enrollment: 40-60
Base Salary: $121k-$150k, commensurate with experience & comparable to SF Archdiocese payscale

Who are we?
Our Lady of the Pillar Academy is a new joyfully Catholic, classical grade school in its 3rd year offering a rigorous, integrated 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. Our classical curriculum combines a broad, liberal arts education with a strong emphasis on developing Christian virtues and an appreciation of beauty. We make it our mission to prepare our students to triumph over the materialism and despair that pervade our culture and accept our Lord's offer to have life and have it abundantly.

Our mission is to build abundant lives in the Half Moon Bay coast side area . . .through Catholic classical education.

Our vision is to cultivate saintly, intellectually well formed, confident children prepared for adulthood and beyond, and to be the school of choice for 220 preschool and primary school students.
Our Lady of the Pillar Academy is located in the middle of the San Francisco Peninsula on the ocean side of San Mateo County, in beautiful Half Moon Bay and within the Archdiocese of San Francisco.

Whom are we seeking?
We are seeking a candidate who will serve as both the Chief Educator and the COO with the title Headmaster who will report to the chairman of the board who is the president & CEO of the institution.
The Headmaster must be a Catholic in good standing with the Church, and is required to take an oath of fidelity to the Church Magisterium on all doctrinal matters, with particular care for those concerning the nature of the human person, sexual ethics, and sexual identity. The ideal candidate is enthusiastic about developing a classical primary school that flourishes, in part, by looking toward the future from the vantage point of tradition. Furthermore, the candidate possesses the natural skills and zeal to draw parents and other stakeholders into the same enthusiasm.

What will you do?
Core Areas of Responsibility

As CHIEF EDUCATOR
Curriculum and Academic Excellence
Faculty Instruction
Student Life and Discipline
Parent Communications
Student Information Systems (SIS)
Student Attraction, Admissions & Enrollment
Student Retention
Teaching Responsibilities (as needed)

As EXECUTIVE DIRECTOR - COO
Business Administration and Other School Operations
Ensure Institutional Stability in collaboration with the board of directors
Fundraising
Marketing/Public Relations
Recruiting
Board Relations
Long term strategic planning
Build systems for efficient, effective and scalable operations
Oversee daily office administration
Safe Environment Coordination

Education/Experience
Post-graduate degree preferred
Significant teaching experience preferably in a classical school environment.
Previous experience in grade school administration.

Certification
Not required

Other Requirements and Reimbursements
Proven ability to engage and inspire a wide range of stakeholders
Provide a certificate of automobile insurance
Maintain a sharp, professional appearance and demeanor; classical formal academia. No sneakers, denim, bare shoulders, low-cut tops, or visible tattoos.
Cooperate with random drug testing.

Compensation & Work Schedule
Base Annual Salary $121k-$150k commensurate with experience
HRA (Health Reimbursement Arrangement) - $6,450 for single employees and $13,100 for employees with families.
2 weeks paid vacation
Paid Holidays

How to Apply
Thank you for your interest! Please email your CV to info@olp.academy. Please include a succinct cover letter introducing yourself and explaining what has you interested in this position.

About the Employer

Our Lady of the Pillar Academy is a new joyfully Catholic, classical grade school in its 3rd year offering a rigorous, integrated 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. Our classical curriculum combines a broad, liberal arts education with a strong emphasis on developing Christian virtues and an appreciation of beauty. We make it our mission to prepare our students to triumph over the materialism and despair that pervade our culture and accept our Lord's offer to have life and have it abundantly.