Headmaster Position

Saint Joseph Classical, A Chesterton Academy – Sioux Falls, South Dakota
Saint Joseph Classical, a member of the Chesterton Schools Network, seeks a dynamic, mission-
driven Headmaster to lead the launch and growth of our new high school in Sioux Falls.
Modeled after the original Chesterton Academy in Minneapolis, our school offers a joyful,
classical education rooted in the Catholic faith and centered on the Incarnation of Jesus Christ.
The Headmaster will serve as the spiritual, academic, and operational leader of the school,
ensuring fidelity to the Catholic mission and to the proven Chesterton Academy curriculum and
culture. This role is critical in shaping the school’s identity, guiding faculty, inspiring students,
and partnering with families to cultivate a vibrant community.

Responsibilities
Spiritual & Mission Leadership
 Foster a culture of faith, charity, and intellectual curiosity rooted in Catholic teaching.
 Ensure all aspects of school life reflect the school’s mission and Catholic identity.
 Collaborate closely with the Chaplain and Board to nurture the spiritual formation of
students, faculty, and families.
Academic & Faculty Leadership
 Oversee the implementation of the Chesterton Academy curriculum.
 Recruit, hire, and mentor faculty committed to Catholic classical education.
 Provide ongoing evaluation, professional development, and support for teachers.
 Ensure high standards of teaching, learning, and student performance.
Student Life & Formation
 Guide the holistic formation of students—intellectual, spiritual, moral, and social.
 Oversee student discipline, ensuring it is consistent, just, and mission-aligned.
 Support extracurricular activities that enrich student life and school culture.
Administration & Operations
 Partner with the Board of Directors on strategic planning and school governance.
 Oversee admissions, enrollment, and family outreach.
 Manage day-to-day operations, including budgeting, scheduling, and communications.
 Represent the school in the broader Sioux Falls and Catholic communities.

Qualifications
 A faithful and practicing Catholic in good standing with the Church, joyfully living and
able to articulate the teachings of the Catholic faith.
 Master’s degree in education, administration, or a related field preferred.
 5 years of teaching and/or school leadership experience, ideally in a Catholic or classical
setting.
 Strong leadership and organizational skills, with the ability to inspire faculty, students,
and families.
 Excellent communication and interpersonal skills.
 Commitment to the classical, Catholic educational model of the Chesterton Schools
Network.

About Saint Joseph Classical, A Chesterton Academy
Opening in Sioux Falls in Fall 2026, Saint Joseph Classical joins a growing network of
Chesterton Academies worldwide. Our school is dedicated to forming the whole person—mind,
body, and soul—through a joyful classical curriculum, daily prayer, participation in the
sacraments, and a strong culture of virtue and friendship.

Application Process
Qualified candidates should submit the following materials:
 Cover letter expressing interest in the position and alignment with the mission.
 Resume/CV outlining educational background and leadership experience.
 Three professional references, including at least one from a pastor, supervisor, or school
leader.
Applications and inquiries may be sent to: shofflander@stjosephclassicalacademy.org