Head of School - Catholic Classical Education Leader

Chesterton Academy of Notre Dame; Madison, Northern (WI, KY); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Chesterton Academy of Notre Dame seeks a Head of School to lead a mission-driven community, formed in virtue, faith, and classical learning, at Holy Name Heights. The leader will deepen Catholic identity and guide a campus expansion to serve more students.

The role calls for virtuous, trusted leadership, strategic planning, and strong communication with the Diocese, families, donors, and faculty. Start July 2027 or earlier; compensation is competitive.

Qualifications

• Must be a practicing Catholic and willing to take an Oath of Fidelity to the Magisterium.
• Leader with integrity, humility, and moral seriousness guiding students, staff, and families.
• Clear and effective communication, sound judgment, and genuine ambition.

Responsibilities

• Lead a mission-driven school community forming students in virtue, faith, and classical learning.
• Deepen the academy's identity as a classical Catholic junior high and high school.
• Oversee the campus expansion at Holy Name Heights for greater capacity in academics, spirituality, and activities.
• Build, attract, develop, and retain outstanding faculty.
• Grow enrollment and financial sustainability through mission-aligned strategic planning.
• Cultivate relationships with the Diocese of Madison, parishes, benefactors, and partner schools.
• Champion accessible Catholic education by increasing tuition assistance and mission-partner giving.
• Serve as the public face and storyteller of the academy to inspire families and donors.

Skills

Profound Faith

Genuine Virtue

Clear Conviction

Inspirational Presence

Servant Leadership

Faculty Development

Job description

Chesterton Academy of Notre Dame seeks a Head of School to lead a mission-driven community, formed in virtue, faith, and classical learning, at Holy Name Heights. The leader will deepen Catholic identity and guide a campus expansion to serve more students.

The role calls for virtuous, trusted leadership, strategic planning, and strong communication with the Diocese, families, donors, and faculty. Start July 2027 or earlier; compensation is competitive.