Executive Director

Chesterton Academy of Annapolis

Annapolis, MD

Job ID#:
11403172776
Posted:
December 5, 2025
Expires:
February 3, 2026
Category:
Fundraising
Terms:
Full-Time Employee
Experience:
0-2 Years
Education:
Undergraduate Degree
Base Pay:
Salary
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Job Description

The Executive Director serves as the chief administrative officer of Chesterton Academy of Annapolis, responsible for the overall leadership, management, and strategic direction of the school in partnership with the Board of Directors and the Headmaster. This role oversees marketing, development, operations, and financial strategy to ensure the school's long-term sustainability and fidelity to its Catholic, classical liberal arts mission.

The Executive Director embraces the mission of Chesterton Academy and the broader vision of launching a new era of education based on the Chesterton model.

The Executive Director must possess strong leadership skills that inspire excellence and cooperation from all constituent groups and demonstrate (1) positive convictions about Chesterton's unique integrated curriculum and dedication to building a culture of life, (2) comprehensive working knowledge of school finance, operations, and budgeting, (3) the ability to promote a strong institutional advancement (fundraising) program, and (4) a commitment to continuing and enhancing strategic planning. Familiarity with public relations and communications and the supervision of facilities will be valuable assets.

The Executive Director must be practicing Roman Catholic, possess the minimum of a Bachelor's Degree and preferably a Master's Degree in Administration or related field and demonstrate a commitment to Catholic secondary education. Salary is competitive and commensurate with experience.

The Board of Directors appoints the Executive Director of Chesterton Academy of Annapolis. A collaborative relationship between the Executive Director and Headmaster is a requirement. The responsibilities of the Executive Director include: (1) daily operations; (2) advancement and fundraising; (2) finances and budgeting; (3) Board of Directors activities and long-range planning.

Primary Responsibilities and Duties
Lead institutional advancement and fund-raising activities to meet and exceed fundraising goals.
Daily operations, including a wide range of school administration including finance, human resources, facilities management, public relations.
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.
Implement policies and directives of the Board of Directors.
Oversee and facilitate long-range planning.
Provide input and direction for the Board of Directors and plan and implement Board formation strategies.
Maintain/establish and implement financial procedures that provide information to the Board and stability to Chesterton Academy of Annapolis
Provide public relations activities that maintain positive communication with key constituents.

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.

Requirements
Education: Bachelor's degree required; advanced degree (e.g. Masters in Administration or related field) preferred.
Experience: Previous experience in administration; secondary school administrative experience preferred; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement
Certification: Not required

About the Employer

Founded in 2018, Chesterton Academy of Annapolis is a member of the growing, international movement that is the Chesterton Schools Network. The mission of Chesterton Academy of Annapolis is to raise up a generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith, abounding in the skills and character requisite for success in college and professional life as well as in building up the kingdom of God, and to excel in service of family, of country, and of Christ our Lord. To that end we seek to form our students intellectually, morally, and spiritually, In the words of G.K. Chesterton, we seek to teach our students that "there is a whole truth of things and that in knowing and speaking it we are happy."