Chesterton Academy of the Immaculate Heart, a member of the growing Chesterton Schools Network, seeks a talented and dynamic full-time headmaster to lead the launch of its new school opening 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 Immaculate Heart. 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 tests (PSAT, ACT, SAT, CLT) 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 (as needed)


Education: Masters in Education or related field
Experience: Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.


Please send cover letter, resume, and three reference letters to Steve Wilson (Chairman of CATIH Board) at



Chesterton Academy of the Immaculate Heart is blessed to have our school location next to St. Peter Church. run by the Canons Regular of St. John Cantius. who will celebrate daily mass for our students.