Chesterton Academy of the St. Croix Valley seeks a talented and dynamic full-time headmaster to lead the transition from satellite campus in Saint Paul, Minnesota to an independent Chesterton network school at its new location in Historic Stillwater, Minnesota beginning in the 2020-21 academic year. This is a rare opportunity for one called to leadership in Catholic, classical education.

The Headmaster serves as the educational and organizational leader and is responsible for implementing the network curriculum, managing the teaching staff, and the policies of the Chesterton Academy of the St. Croix Valley. He or she is responsible for instructional leadership (teacher growth and development), curriculum and school recommendations, hiring and supervision of instructional personnel, student life, discipline, and all related parent communications.

The headmaster will ensure that students are in a learning environment to maximize both faith and reason, in order that they develop God-given talents and gifts and find joy in their ultimate calling. We seek to lead and transform through beauty, truth and goodness.

Responsibilities include:

Curriculum and Academic Excellence
• Oversee adherence to and any changes to the curriculum
• Collect course materials for each class (syllabus, weekly teaching plan, tests)
• Review results of student standardized tests (Classical Learning Test Suite (CLT) or other national tests) and make stipulations regarding course content and delivery as needed
• Oversee school accreditation process and renewal

• Oversee faculty hiring, evaluation, rehires, terminations
• Conduct classroom observations for faculty members as part of evaluation process

Student Life and Discipline
• Ensure discipline policies are enforced, communicated
• Oversee parent-led sports and extracurricular activities
• Ensure effectiveness of virtue house and faculty mentor programs
• Oversee academic and behavioral eligibility for extra-curricular activities

Parent Communications
• Send weekly Headmaster Missive to parents
• Meet with parents regarding student discipline and academic issues

• Admit new students upon review of placement exam, student application materials, and meeting
• Oversee transfer student process (curriculum, regulations, forms, financial)
• Review placement tests and contact parents with remedial needs
• Deliver presentations to prospective parents and students at selected school events

• Coordinate standardized testing, college applications and transcript preparation
• Communicate with colleges, universities and other post-high school programs
• Promote various vocational opportunities

Other School Operations
• Oversee selection and evaluation of vendors (software, textbooks, other services)

Teaching Responsibilities
• In these early years of growth of the academy, the headmaster will be a key member and leader of the faculty by teaching a half-time to three quarter-time teaching load.


Experience: Six to ten years of teaching experience in a classical school environment; three to five years of experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church. Less important but an added bonus, a working knowledge of institutional advancement/fundraising.

Education: Preference for a masters-degree or higher level of education in a key academic subject of the Chesterton Academy curriculum. (Theology, Philosophy, Literature, Mathematics, Science, the Arts.)


Interested candidates should submit a cover letter, resume, and three to five references to



Founded in as a result of a grass-roots movement of parents in the Fall of 2017, Chesterton Academy of the St. Croix Valley offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. A member of the Chesterton Schools Network, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about Chesterton Academy of the St. Croix Valley and the growing national Chesterton Schools Network at