Now Hiring: School Administrator

Careers
Written By Madeline Williams

Seeking Full-Time School Administrator
Reports to: Headmaster and Board of Trustees

Chesterton Academy of the Immaculata, a new co-ed high school in MetroWest, Boston serving grades 9-12, seeks a joyful, mission-driven and experienced Administrator for the 2025-2026 school year. The Administrator plays a vital leadership role in the daily operation of the school, working closely with the Headmaster and Board of Trustees to ensure that administrative, financial, and operational systems run smoothly and in full alignment with our Catholic mission.

Qualifications

  • Bachelor's degree required; advanced degree preferred

  • Experience in secondary school administration strongly preferred

  • Practicing Catholic able to take the Oath of Fidelity to the Magisterium.

  • Excellent organizational, written, and verbal communication skills

  • Professional and joyful demeanor

  • Experience working in Catholic education or mission-driven organizations is a plus

    Key Responsibilities

    1. Administrative Operations

  • Oversee daily school office functions and general administration

  • Maintain student records, staff files, and the master school calendar

  • Coordinate school-wide communications: newsletters, alerts, forms, etc.

    2. Admissions & Enrollment

  • Manage inquiries, tours, applications, and enrollment process.

  • Maintain admissions and enrollment databases.

  • Support onboarding of new families and organize open houses.

    3. Business & Financial Administration

  • Collaborate with the Board and Treasurer on financial oversight

  • Manage tuition tracking and billing (via TADS or equivalent)

  • Assist with budgeting, invoice management, purchasing, and vendor coordination

    4. Facilities and Safety

  • Ensure a clean, safe, and secure campus environment daily

  • Coordinate routine maintenance, inspections, and emergency drills

    5. Technology and Systems Oversight

  • Maintain school IT systems (internet, printers, devices)

  • Coordinate with IT support as needed

  • Manage systems for attendance, grading, communication, and digital records

    6. Support for School Leadership & Board

  • Assist with staff HR paperwork, background checks, and compliance tracking.

  • Assist with planning and logistics for various school events and activities

  • Provide administrative support for the Headmaster and Board of Trustees

  • Coordinate school calendar and scheduling logistics

    7. Advancement & Fundraising Support

  • Assist in coordinating fundraising efforts, including planning for the annual gala

  • Track donor information and maintain fundraising records

  • Support donor communications, acknowledgments, and event logistics

  • Collaborate with leadership to identify and pursue grant opportunities

    8. Parent, Faculty & Community Relations

  • Serve as a welcoming and professional presence in the front office.

  • Greet and assist students, parents, visitors, and vendors in a warm and efficient manner

  • Answer phone calls and emails; route messages and inquiries appropriately

  • Respond to parent and visitor inquiries with clarity and charity

  • Help maintain a culture of joy, order, and Catholic identity across the school day.

    To Apply

    Please send the following materials to the Chair of the Board of Directors, Nathalie Calvo, at careers@chestertonimmaculata.org:

  • A cover letter explaining how your experience reflects the mission and qualifications of the role.

  • A curriculum vitae.

  • Three professional references (include name, relationship, phone number, and email)

  • One pastoral reference.

    Applications are reviewed on a rolling basis.

    About the Employer

Chesterton Academy of the Immaculata is a member of the Chesterton Schools Network, sponsored by the G.K. Chesterton Society. chestertonschoolsnetwork.org

Under the patronage of our Blessed Mother, Chesterton Academy of the Immaculata seeks to partner with parents in forming young men and women to be joyful leaders and saints. We cultivate Christian virtues and guide students in the pursuit of Truth, Goodness and Beauty. By providing a rigorous, classical, Catholic education faithful to the Magisterium, we inspire our students to be disciples of Christ and bear witness to a culture of life. www.chestertonimmaculata.org

Madeline Williams
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