Headmaster – High School

The Headmaster of Chesterton Academy of Our Lady of Hope serves as the educational and spiritual leader of the school. The Headmaster, in collaboration with the Executive Director, is responsible for communicating and implementing the school’s mission and vision by fostering a community of friends seeking to grow in wisdom, virtue, and faithfulness to Christ and His Church. The headmaster will oversee academics, the formation of student and faculty culture, and day-to-day educational operations, including mentoring teachers.

The Headmaster and the Executive Director will be the ambassadors for the school to current and prospective families. The headmaster, along with the Executive Director, serves as the leadership of the school and its operations. Both will report to the Board of Directors and be supported by operations and academic staff for the overall success of the school.

Chesterton Academy of Our Lady of Hope exists exclusively for charitable, religious, and educational purposes, specifically to help parents raise up a new generation of joyful leaders and saints. This is achieved by educating our students in the Catholic classical, liberal arts tradition and values of the Chesterton Academy model both rooted in the truths of the Catholic faith, to serve the common good.

We seek to form young men and women who know and love the truth, and magnify Jesus Christ, Truth himself, with their lives. Chesterton students read the Great Books, take advanced math and science courses, study Latin, engage meaningfully with their external community, care for plants and animals, explore the fine arts, and can participate in extracurricular clubs and athletics, all guided by the light of the Catholic faith.

In conjunction with rigorous academics, Chesterton is committed to building a transformative school culture filled with joy, respect, and deep engagement. Chesterton’s teachers and school leaders inspire students to pursue excellence in all areas of their lives and reach their fullest potential. Our pedagogy is focused on developing the dispositions that enable deep attention and wonder, a love of tradition, and the capacity for fruitful inquiry in a community of friends.

We partner with parents to foster a community of learning, prayer, and friendship, centered in the Eucharist.

• Responsible for all Academic operations
• Oversee and mentor the Dean of Student Life (discipline, prefects, house system, student life events and initiatives), the Dean of Academics (grade books oversight, implementing CSN Curriculum, student academic support, college applications counseling, administrative support), and Teachers.
• Lead the hiring of the academic staff, supported by the Executive Director and the administrative staff for HR related matters
• Oversee the implementation of curriculum in the Catholic Classical Liberal Arts and Chesterton School Network model.
• Actively participate in professional networks, including but not limited to CSN.
• Support School Resource Development efforts
• Collaborate with School leadership team for greater community outreach.
• Oversee school liturgies (daily Mass, morning and evening prayer, class prayer), encourage students in spiritual life, and provide opportunities for Confession
• Communicate internally and externally with staff, students, parents, and the community. Example:
  Weekly newsletter, weekly faculty meeting
• Play a key role in recruitment, admissions, and enrollment of students, including student and family interviews
• Maintain compliance with program policies, rules, and regulations
• Maintain program budget in conjunction with the Executive Director and the Board of Directors
• Attend and participate in all board meetings with Headmaster’s report
• Develop enrichment opportunities for students and staff
• Implement initiatives for community building and parent formation
• Collaborate with the Director of Operations for the safety of the students and faculty on campus, and assist with the development of a site emergency preparedness plan
• Oversee parent-led sports and extracurricular activities

• Love of our Lord Jesus Christ, Children, the Catholic…