Website Chesterton Academy - Queen of Martyrs Sun Prairie, Wisconsin

As the founding headmaster, this position will have a substantial and immediate impact on the development of our school. We are seeking a faithful, joyful disciple of Jesus Christ, who has a passion for classical education, forming a rich Catholic community, and building a healthy and thriving institutional culture.

The headmaster serves as the educational leader of Chesterton Academy – Queen of Martyrs. As the public face of the school, the headmaster must be able to spark Catholic joy and inspire sacrificial service in students, parents, staff, and our broader community. Energy, patience, organization, self-confidence, practicality, and gracious tact, with the ability to say no when necessary, are all part of the job. The headmaster is responsible for implementing the policies that ensure all students are supervised in the learning environment, that adhere to our Catholic identity, and that meet the approved curricula and mission of the school.

We are looking for a joyful, prayerful servant leader who is not only a capable administrator, but also one who loves educating youth and has a passion for the formation of the whole human person. The headmaster is responsible for the curriculum and instructional leadership of the school, hiring and supervision of instructional personnel, student recruitment, student life, discipline, and related parent communication. The applicant must know how to hire and develop faculty who can effectively teach, love, and inspire their students.

The headmaster at Chesterton Academy – Queen of Martyrs will adopt the missionary spirit of the founders, who seek to provide an integrated high-school curriculum centered on Christ’s Incarnation.

This time is a pivotal one for prospective families; it requires a sharp leader who is determined to bring into existence an exceptional educational community that would be otherwise unavailable to the east side of Madison. But the opportunity is also a challenge. The work ahead requires a leader with a robust vision for Catholic education—one who is ready to tackle difficult topics and decisions with faithful discernment, all the while overseeing and protecting the hearts and minds of students.

Ultimately, the headmaster helps to create and preserve a joyful learning environment that cultivates virtue and teaches students to embody truth, goodness, and beauty.


The Board of Directors appoints the headmaster of Chesterton Academy. A collaborative relationship between the headmaster and Board of Directors is a requirement. Together they share the responsibilities of nurturing and maintaining the mission and traditions of the school, as well as ensuring fidelity to the Magisterium of the Catholic Church. The headmaster reports to the Board and will serve as ex-officio on the Board.


Must be practicing Roman Catholic and demonstrate a commitment to Catholic secondary education (Required)
Bachelor’s Degree (Required)
Master’s Degree (Preferred)
4 + years of experience in secondary school teaching or administration (Preferred)
2+ years teaching experience in a classical school environment (Preferred)
1+years of experience overseeing non-profit/for-profit fundraising (Preferred)
Exposure to a classical school environment, whether through attending, teaching or administration
Experience in hiring and managing teams or personnel
Exemplary verbal and written communication skills
Resilient and adaptable with strong time management and organizational skills as well as problem solving abilities.
Committed to the mission of Chesterton Schools Network and the teachings of the Catholic Church.
>Salary is competitive and commensurate with experience.


Candidates may familiarize themselves with the Chesterton Schools Network and Chesterton Academy – Queen of Martyrs. If interested in applying for this position, please forward a cover letter, resume, and three professional references to No third party inquiries please.


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