Contact [email protected]

Chesterton Academy of St James
Redwood City, CA

Chesterton Academy of Saint James seeks a vigorous, effective leader to serve as its inaugural Headmaster starting in Fall 2022. Headmaster job starts full time on June 1, 2022. Part-time work will be requested before June 1, 2022.

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The Headmaster "owns" the job of delivering our classical curriculum effectively and joyfully per the model to our students. This individual is responsible for the school's instructional leadership, hiring, and supervision of instructional personnel, the curriculum, student life, and other related internal operations. Additionally, he will assist with some recruiting, fundraising, and other external activities.

Whom are we seeking?

The Headmaster serves as the educational leader effectively and efficiently managing the systems, procedures, and culture of a joyful, protected, fruitful learning environment in keeping with Catholic Tradition and the approved curricula and mission of the school. This individual will also maintain discipline and related parent communication.
The Headmaster must be a Catholic in good standing with the Church, who assents 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 Candidate will possess a zeal for our Lord in producing a joyfully classical education environment from the vantage point of Catholic Tradition, with an ability to speak comfortably and competently with various stakeholders.

What will you do?
1. Curriculum and Academic Excellence
• Oversee adherence to Chesterton Schools Network curriculum
• Oversee implementation of changes to the curriculum
• Review results of student tests (e.g., CLT, PSAT, ACT, SAT)
• Oversee school accreditation process and renewal per Network guidelines
2. Instruction
• Oversee faculty hiring, evaluation, rehires, terminations
• Conduct classroom observations for faculty members as part of the evaluation process
• Develop, mentor and lead each faculty member in personal and professional growth.
3. Student Life and Discipline
• Ensure discipline policies are enforced, communicated
• Oversee parent-led sports and extracurricular activities
• Ensure effectiveness of Chesterton virtue houses and faculty mentor programs
• Oversee academic and behavioral eligibility for extracurricular activities
4. Parent Communications
• Send weekly Headmaster Missive to parents
• Meet with parents regarding student discipline and academic issues
5. Admissions
• Admit new students upon review of the placement exam, student application materials, and interview results
• Oversee transfer student process (curriculum, regulations, forms, financial)
• Review placement tests and contact parents of students with remedial needs
• Deliver presentations to prospective parents and students at selected school events
6. Guidance
• Coordinate standardized testing, college applications, and transcript preparation
• Communicate with colleges, universities, and other post-high school programs
• Promote various vocational opportunities
7. Other School Operations
• Oversee selection and evaluation of vendors (software, textbooks, other services)
8. Teaching Responsibilities (as needed)

• Board of Directors - Reporting, weekly
• Executive Director - Consultative and collaborative, daily
• Faculty & Staff - supervisory, daily
• Students - lead by example, daily
• Parents - weekly or more as needed

Knowledge & Skill Requirements:
• Abundance mindset
• Integrity, honesty, and commitment to excellence
• Strong written and verbal communication skills
• Strong organization, multi-task, and project management abilities
• Strong email and phone message monitoring and management skills
• Strong ability to stay focused and exceptional attention to detail
• Must have a service-based attitude and ability to remain calm under pressure
• Team Player

• Post-graduate degree preferred
• Significant teaching experience in a classical school environment.
• Previous experience in secondary school administration.
• Familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church.
• Working knowledge of institutional advancement/fundraising.
• Not required

Other Requirements and Reimbursements

• Practicing Catholic who is committed to Catholic secondary education.
• Gravitas and credibility to proudly represent an outstanding refreshingly classical liberal arts Catholic high school in the San Francisco Bay Area

• Exceptional communication and interpersonal skills, including a proven ability to engage and inspire a wide range of stakeholders from young students to parents and contributors.
• Significant visionary leadership and management skills to address immediate organizational needs while keeping sight of long-term goals.
• An inspiring presence to encourage confidence and passion in a positive work environment and the maturity and wisdom required to energize Board members' engagement in the mission.
• Fundraising, recruiting, marketing skills, and familiarity with budgets and operations.
• Maintain a California Driver's License in good standing.
• Provide and maintain in good condition your own automobile appropriate for travel to school
functions, travel to training sessions, and as needed otherwise. Your automobile must be insured up 100/300/100 limits. You are required to provide to Chesterton Academy of St. James a certificate of automobile insurance naming Chesterton Academy of St. James as additional insured.
• Chesterton Academy of St. James will reimburse you for your automobile mileage driven exclusively for school business. You are required to submit a log of reimbursable mileage showing the date, description of exclusive business mileage, starting location, ending location, and quantity of miles for each log entry. Mileage logs should be submitted to your supervisor on the 1st of the month or following business day, and reimbursements will be paid monthly on the 10th or following business day.
• Maintain a sharp, professional appearance and demeanor at all times, business formal or business casual, depending on the situation. No denim, corduroy, bare shoulders, low-cut tops, or visible tattoos.
• Maintain a tidy workstation and contribute to a clean, professional look.
• All school expenses should be paid on school charge accounts, but if in certain exceptions you
need to pay for an authorized school expense with your personal cash or charge account Chesterton Academy of St. James will reimburse you for the approved business expense. A receipt is required for reimbursement.
• Provide your own smartphone for use on the job. You will receive a monthly reimbursement of $25 for school use.
• Cooperate with random drug testing.

Compensation & Work Schedule
• Base Annual Salary $125k-$175k commensurate with experience
• HRA (Health Reimbursement Arrangement) - $5,000 for single employees and $10,000 for
employees with families.
• Paid vacation per a written schedule - begins to accrue after 90 days of employment.
• Paid holidays
• This position will require a minimum of 40 hours per week plus a willingness to devote
additional time as needed for board meetings, community and donor events, and other meetings that occasionally occur in the evenings and on weekends.

How to Apply
Thank you for your interest! Please email your CV to [email protected]. Please include a succinct cover letter introducing yourself, explaining what has you interested in this position and what is your availability for part time work between now and June 1, 2022.

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