Head of School

Napcis

Madison (WI)

On-site

USD 120,000 - 180,000

Full time

14 days+
Application generator

Stand out for this role — generate a tailored resume and cover letter in about a minute.

Get past ATS filters

Job summary

St. Ambrose Academy invites a Head of School to steward its classical Catholic identity while guiding the school into a new chapter at Holy Name Heights.

The role focuses on forming students in virtue, faith, and classical learning; building faculty, expanding enrollment, and strengthening ties with the Diocese, benefactors, and partner schools.

Qualifications

  • Catholic faith expressed in life and leadership.
  • Demonstrated integrity, humility, and moral seriousness.
  • Clear, effective communicator with sound judgment.
  • Visible servant-leader presence, accessible to all.
  • Ability to coach and develop faculty aligned with mission.

Responsibilities

  • Lead a mission-driven school community in forming students in virtue, faith, and classical learning.
  • Strengthen the Academy's identity as the only accredited classical Catholic junior high and high school in the Diocese of Madison.
  • Oversee the new Holy Name Heights campus and its expanded capacity for academic, spiritual, and extracurricular programs.
  • Develop and retain outstanding faculty and support high-quality instruction.
  • Grow enrollment and financial sustainability through strategic planning and outreach to families in the Madison region.
  • Strengthen relationships with the Diocese of Madison, parishes, benefactors, and partner schools.
  • Champion tuition assistance and mission-partner giving to make Catholic education accessible.

Skills

Catholic faith
Executive leadership
Strategic planning
Communication skills
Community engagement

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

Get your free, confidential resume review.
or drag and drop your file here.
Similar jobs

Similar jobs worth comparing

Full-Time Head of School
Full-Time Head of School

Ambroseacademy • Madison (WI)

On-site
USD 110,000 - 190,000
Visionary Head of School — Classical Catholic Academy
Visionary Head of School — Classical Catholic Academy

Ambroseacademy • Madison (WI)

On-site
USD 110,000 - 190,000
Assistant Head of School
Assistant Head of School

Classical Christian Schools • Midwest (WY)

On-site
USD 90,000 - 130,000
Health Benefits
Tuition remission for children of facu
Professional development opportunities
Headmaster
Headmaster

Chesterton Academy of Notre Dame • Town of Sun Prairie (WI)

Hybrid
USD 90,000 - 150,000
Head of School Mount Mercy Academy
Head of School Mount Mercy Academy

Catholic Diocese of Buffalo  • Buffalo (NY)

On-site
USD 100,000 - 125,000
Tuition reimbursement
Comprehensive benefits package
Head of School
Head of School

Acara Solutions, Inc. • Buffalo (NY)

On-site
USD 100,000 - 125,000
Comprehensive benefits package
Tuition reimbursement
Headmaster: Agape Christi Academy
Headmaster: Agape Christi Academy

Classical Christian Schools • Midwest (WY)

On-site
USD 120,000 - 160,000
Head of School
Head of School

ServingSchools • Waterville (ME)

On-site
USD 120,000 - 170,000
Head of Upper School
Head of Upper School

The Covenant School • Pepper Pike (OH)

On-site
USD 70,000 - 90,000
Head of Academic Upper School
Head of Academic Upper School

Islamic League of America • Austin (TX)

On-site
USD 80,000 - 100,000