HeadmasterSociety of Gilbert Keith Chesterton

We're looking for someone with 3-5 years of experience as an educational leader to serve as our Headmaster. This pivotal role requires a dedicated individual who can provide visionary leadership while maintaining our academic standards and institutional values. You'll oversee all aspects of school operations, from curriculum development to budget management, while fostering a thriving learning environment. The ideal candidate will bring both educational expertise and a commitment to our mission and faith-based principles.

• 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 (gradebooks 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

• Communication 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

• Attendance and participation 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 Faith, and Classical Liberal Arts tradition and education

• Faithful Catholic in good standing with the Church. Faithful to the teachings of the Church and actively involved in the practice of faith

• A man or woman of strong character, committed to providing a Gospel witness

• Able to develop intentional processes and procedures that support a school culture of joy, respect, and deep engagement

• Able to cultivate a beautiful student culture and joyful discipline

• Keen ability to be a mentor and coach faculty for ongoing development.

• Minimum 3-5 Years of secondary-level teaching and 2+ years of school administrative experience.

• Master's Degree or PhD preferred.

• Timely and effective communication to staff, children, parents, and broader community of supporters.

• Understanding of financial budgets and planning processes.

• Understanding of common standards for school operations: Safety, Compliance, Recordkeeping, etc.

• Ability and willingness to engage the greater community with information about CAOLH and the great work being done.

Please forward a cover letter, curriculum vitae and 3 professional references to the following email: HMsearch@chestertonri.org

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.