Executive Director

Executive Director

Chesterton Academy of Milwaukee

Now in its 10th year of operations, Chesterton Academy of Milwaukee is a flagship school in the Chesterton Schools Network. The Academy joyfully offers a Catholic, classical liberal arts education that forms students in faith, reason, and virtue.

Reports to:

Board of Directors

Supervises:
Development Manager, Marketing Manager, Office Manager

The Executive Director serves as the chief administrative officer of Chesterton Academy of Milwaukee, 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.

• Direct all fundraising and advancement efforts to meet and exceed annual giving goals. Cultivate and steward donors, alumni, and community partners.
• Develop and implement a comprehensive marketing and admissions plan to promote enrollment growth and enhance the visibility of the Academy's mission.
• Oversee daily operations of the school, including finance, human resources, and facilities management. Ensure smooth and effective administrative processes and communications.
• Collaborate with the bookkeeping firm and Treasurer to establish and maintain sound financial procedures. In collaboration with the Treasurer, manage budgets and provide timely financial reports to the Board.
• Collaborate closely with the Board of Directors to identify, create, and implement strategic plans that sustain business objectives and advance the mission of the Academy.
• Train and supervise a talented team of employees and managers who can lead critical areas of the school's operations and functions.
• Develop and organize systems to monitor operations and performance within each functional area, ensuring efficiency, accountability, and alignment with strategic goals.
• Attend and prepare reports for quarterly board meetings. Implement policies and directives of the Board.
• Supervise and support the Development, Marketing, and Office Managers; ensure alignment of their work for excellence and in the goals of the school.

• Bachelor's degree required; advanced degree preferred.
• Prior experience in development, marketing, administration, or related leadership roles strongly desired.
• Strong organizational, communication, and leadership skills with the ability to elicit cooperation across multiple constituencies.
• Demonstrated ability in financial planning, fundraising, and operational management.
• Practicing Catholic in good standing, with a deep appreciation for and commitment to the Catholic, classical liberal arts education model championed by Chesterton Academy.

The successful candidate will be mission-driven, collaborative, strategic, and inspired by the opportunity to advance the formation of joyful, faithful, and intellectually vibrant young people in the Chesterton tradition.