Headmaster

CatholicJobs.com; Town of Sun Prairie (WI); On-site; USD 85,000 - 110,000; Full time

Job summary

Chesterton Academy - Queen of Martyrs in Sun Prairie, Wisconsin, is seeking an experienced Headmaster to guide the school as its visionary educational and instructional leader. The Headmaster will cultivate a Catholic, classical school culture, support faculty, oversee academics, student life, and collaborate with the Executive Director.

The ideal candidate will be a practicing Roman Catholic, hold at least a Bachelor's degree with a Master's preferred, have experience in classical education,

Qualifications

• Bachelor's degree required; master's degree in education, educational administration, school leadership, or related field preferred.
• Significant experience teaching in a classical school environment.
• Demonstrated excellence as a classroom teacher.
• Deep knowledge of classical education and pedagogy.
• Experience supervising, mentoring and developing educators.
• Educational administration or instructional leadership experience preferred.
• Must be a practicing Roman Catholic in full communion with the Catholic Church.

Responsibilities

• Lead and form the faculty through mentoring, coaching, classroom observation, professional development, and evaluation.
• Lead recruitment efforts to hire teachers.
• Supervise and retain teachers who embrace the school's mission.
• Oversee curriculum and academic excellence with faithful implementation of Chesterton curriculum.
• Provide instructional leadership to develop classical pedagogy, classroom management, and student engagement.
• Oversee student life and discipline, promoting formation of students.
• Communicate with students, parents, and faculty on academic and behavioral matters.
• Participate in admissions and prospective-family meetings.
• Oversee academic guidance, testing, transcripts, college planning, scheduling, and policies.
• Collaborate with Executive Director and Board to grow the school.

Skills

Leadership

Educational leadership

Teacher development

Classical education

Education

Bachelor's degree

Master's degree in education/administration

Job description

Chesterton Academy - Queen of Martyrs

Sun Prairie, WI

Job ID#: 14431177130

Posted: September 2, 2026

Expires: November 1, 2026

Category: Secondary Education

Terms: Full-Time Employee

Experience: 2-5 Years

Education: Undergraduate Degree

Base Pay: Salary

For your privacy and security, when applying for a job, never provide your social security number, credit card number or bank account information to a prospective employer. To use this website, you must accept and comply with our Terms of Service.

Job Description

Chesterton Academy - Queen of Martyrs | Sun Prairie, Wisconsin

Chesterton Academy - Queen of Martyrs is seeking an experienced, mission-driven Headmaster to serve as the school's visionary educational and instructional leader. The Headmaster will help cultivate a strong Catholic, classical school culture, lead and support our faculty, oversee academics, student life, and guide the development of our growing school.

The Headmaster works closely with the Executive Director in a model of shared leadership and collaboration. While the Executive Director oversees the business and operational aspects of the school, the Headmaster leads the internal academic life of the school, including faculty, curriculum, instruction, student formation, and discipline.

Key Responsibilities

• Lead and form the faculty through mentoring, coaching, classroom observation, professional development, and evaluation.
• Lead the recruitment efforts to hire teachers.
• Supervise, and retain excellent teachers who embrace the mission of Chesterton Academy.
• Oversee curriculum and academic excellence, ensuring faithful implementation of the Chesterton Schools Network curriculum and classical Catholic educational philosophy.
• Provide instructional leadership, helping teachers grow in classical pedagogy, classroom management, discussion, assessment, and student engagement.
• Oversee student life and discipline, promoting the intellectual, moral, spiritual, and human formation of students.
• Communicate effectively with students, parents, and faculty regarding academic, behavioral, and student-life matters.
• Participate in admissions and prospective-family meetings, helping families understand the school's Catholic and classical educational philosophy.
• Oversee academic guidance, testing, transcripts, college/post‑secondary planning, scheduling, and academic policies.
• Collaborate with the Executive Director, Board of Directors, Academic Dean and Chesterton Schools Network to advance the mission and growth of the school.
• Depending on the needs of the school and the candidate's expertise, the Headmaster may also maintain a teaching assignment.

The Ideal Candidate Will

We are seeking an experienced classical educator and proven instructional leader who combines excellent teaching ability, strong leadership skills, and a deep commitment to Catholic education.

Required Qualifications

• Bachelor's degree required; master's degree in education, educational administration, school leadership, or a related field preferred.
• Significant experience teaching in a classical school environment.
• Demonstrated excellence as a classroom teacher.
• Deep knowledge and practical experience with classical education and pedagogy.
• Experience supervising, mentoring and developing educators.
• Previous educational administration or instructional leadership experience strongly preferred.
• Knowledge of the Chesterton Schools Network and its educational philosophy preferred.
• Must be a practicing Roman Catholic in full communion with the Catholic Church and committed to Catholic education and the teachings of the Catholic Church.

What We Are Looking For

Above all, we are looking for a teacher of teachers, a leader who understands excellent teaching firsthand, knows why classical education matters, and can help other teachers grow in their vocation as educators.

The Headmaster should be a leader who forms teachers rather than simply manages them, builds a unified faculty rather than a collection of individuals, and helps create a school culture where teachers flourish, students flourish, and the Catholic faith is lived and loved.

About The Employer

The mission of Chesterton Academy - Queen of Martyrs is to aid parents in raising up a new generation of joyful leaders who are faithful to the Magisterium of the Catholic Church and striving to be counted among the saints. Students will engage in the pursuit for the Truth through our content-rich and integrated classical Chesterton Schools curriculum.

ChestertonQofM.com