Executive Director

Executive Director

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.

• Strong leadership skills that inspire excellence and cooperation from all constituent groups.
• Positive convictions about Chesterton’s integrated curriculum and dedication to building a culture of life.
• Comprehensive working knowledge of school finance, operations, and budgeting.
• Ability to promote a strong institutional advancement (fundraising) program.
• Commitment to continuing and enhancing strategic planning.
• Familiarity with public relations and communications and supervision of facilities.
• Practicing Roman Catholic.
• Minimum of a Bachelor’s Degree (preferred Master’s Degree in Administration or related field).
• Commitment to Catholic secondary education.

• The Executive Director reports directly to the Board of Directors.
• Maintains a consultative, collaborative relationship with the Headmaster.
• Maintains a supervisory relationship with selected staff.

• Education:
  
  Bachelor’s degree required; advanced degree (e.g., Master’s 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.

Salary is competitive and commensurate with education and experience.