Head of School

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

Job Description

The next Head of School will serve as the primary guardian and champion of the Academy's classical Catholic identity, while leading the institution into a promising new chapter at its beautiful Holy Name Heights campus.

• Lead a dynamic, mission-driven school community in forming students in virtue, faith, and classical learning
• Deepen and strengthen the Academy's identity as the only accredited classical Catholic junior high and high school in the Diocese of Madison
• Steward the Academy's exciting new chapter at Holy Name Heights - a beautiful, purpose-built campus with expanded capacity for academic, spiritual, and extracurricular programs
• Build on strong academic outcomes by continuing to attract, develop, and retain outstanding faculty
• Grow enrollment and financial sustainability through mission-aligned strategic planning,including expanding the school's reach to new families across the Madison region
• Cultivate deep relationships with the Diocese of Madison, supporting parishes, benefactors, and partner schools to strengthen the Academy's community and resource base
• Champion the Academy's commitment to accessible Catholic education by growing its tuition assistance program and mission-partner giving
• Serve as the public face and storyteller of St. Ambrose Academy - inspiring families, alumni, and donors with the transformative power of a classical Catholic education

Requirements

The candidate must be a practicing Catholic, willing to make an Oath of Fidelity to the Magisterium, whose life of faith serves as an example to our students and families. Desired qualifications and attributes include:

• A Person of Profound Faith: Our Head of School must embody the Catholic faith, not simply manage a Catholic institution.
• A Leader of Genuine Virtue: A virtuous leader whose character is beyond question -someone whose integrity, humility, and moral seriousness sets the tone for every student, faculty, and staff member; in every conversation, and decision.
• Clarity & Conviction: Clear and effective communication skills, sound judgment, and genuine ambition. A leader who makes decisions that people trust, even when those decisions are difficult.
• Inspirational Presence: Energy, warmth, and a contagious sense of purpose that students and families feel from the first encounter.
• The Heart of Servant Leader: The Head of School is not above it -they are woven into it. Our next leader will be present, accessible, and genuinely invested in the flourishing of every person in the building.
• A Builder of Faculty Culture: Our teachers are deeply mission-aligned and talented. They are looking for a leader who invests in them - who coaches, challenges, and recognizes our mission advancement.

Start Date: July 2027 or earlier

Compensation: Competitive

More Information: https://ambroseacademy.org/wp-content/uploads/2026/07/SAA-Head-of-School_Career-Opportunity.pdf