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Assistant Headmaster of Operations

The Chesterton Schools Network

The Chesterton Schools Network

Operations
Warwick, RI, USA
Posted on Jul 1, 2025

Job Description

Responsibilities:

The Assistant Headmaster of Operations coordinates and manages operations for the school, and assists in strategic planning and new initiatives. Responsibilities may include:

Manage student recruiting and enrollment

Depending on the needs of the team, serve as or supervise registrar, bursar, office manager, communications and marketing team, and facilities maintenance and staff

Manage volunteer projects, such as building and campus improvements

Maintain/establish and implement financial procedures that provide information to the Headmaster and Board, and stability to Chesterton Academy

Monitor and ensure the organization stays on budget for the current year

Work with finance committee on preparing the budget for the next year

Manage operational regulatory requirements such as required building inspections, educational statutes

Insurance Renewals, Title I and Title II Applications

Manage Accreditation Process

Assist in event planning and logistics coordination

Emergency Response planning coordination

Assist in fundraising and strategic planning

Oversee management of student records

Other duties as assigned

Mission and Vision

Our Lady of Hope's mission is to form young men and women who know and love the truth, and magnify Jesus Christ, Truth Himself, with their lives. We partner with parents to foster a community of learning, prayer, and friendship, centered in the Eucharist, so that our students become joyful leaders and saints.

Chesterton students read and discuss the Great Books, take advanced math and science courses, study Theology and Latin, engage with the natural world, practice the fine arts, have the opportunity to participate in clubs and athletics, attend Mass daily, and offer all things in prayer.

Chesterton is committed to building a school culture characterized by joy, respect, faithfulness, and deep engagement. Chesterton teachers and school leaders inspire students to pursue excellence in all areas of their lives and reach their fullest potential.

Hiring Profile

Mission and vision alignment
Strength of character
Love of learning & desire to grow
Commitment to collaboration and team unity
Strong work ethic and an enthusiastic, positive attitude
At least 2-3 years of classroom teaching experience or understanding of the classroom environment
Evidence of Operational Excellence
Working knowledge of administrative practices and procedures, as well as experience leading in a Catholic environment
Practicing, fully initiated Catholic, willing to take an oath of fidelity to the magisterium of the Catholic Church

About the Employer

Chesterton Academy of Our Lady of Hope exists exclusively for charitable, religious, and educational purposes, specifically to help parents raise up a new generation of joyful leaders and saints, educated in the classical, liberal arts tradition and the truths of the Catholic faith, in order to serve the common good.