Headmaster

Job Description

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

Montessori Primary Lead Guide
Competitive Compensation Package
High Quality of Life Location

St. Joseph Academy, a hybrid, Catholic, classical school in Sioux Falls, SD, is seeking a
Montessori 3-6 Lead Guide for the 2025-2026 school year. Join a faculty of teachers and
parents on a mission to impart the love of truth, beauty, and goodness.

Ideal candidates:
Certified 3-6 Montessori Guide (AMI).
Are passionate about working with children ages 3-6 and supporting home-educating families.
Implement the Montessori philosophy and curriculum tailored to the developmental needs of children ages 3-6.
Create and maintain a beautifully prepared environment that fosters independence, self-discipline, and confidence in each child.
Integrate outdoor experiences.
Direct and collaborate with one assistant.
Work between 7:30 a.m. and 3:30 p.m. Monday, Tuesday, Wednesday, and Thursday, August through May, following an academic calendar.
Collaborate and communicate with parents and faculty to support the holistic development of our littlest saints-in-training.
Embrace our founding ethos of faithfulness to the Catholic Church and love of Jesus.

Send resume and cover letter to shofflander@stjosephclassicalacademy.org

About the Employer

St. Joseph Classical, a Chesterton Academy is raising up a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. This Chesterton Academy will serve high school students in grades 9-12 beginning with grade 9 in fall 2026. Chesterton Academy offers a rigorous, integrated curriculum that unlocks their potential and prepares them to succeed in college, professional life, and to excel in service of family, country, and Christ our Lord. St. Joseph Classical, a Chesterton Academy is an extension of St. Joseph Academy and a member of the international Chesterton Schools Network.