Headmaster Edit listing

Now entering its fourth year of operations, Chesterton Academy of Our Lady of Hope is a growing school in the Chesterton Schools Network, with its own 3-acre campus, including a school and a full church that seats 400. Over the past 3 years, with full diocesan support, more than 70 priests have celebrated daily Masses in our beautiful campus chapel. Our faculty and staff have doubled for this coming year, and we're seeking a leader to help grow the school to the next level.

The Headmaster of Chesterton Academy of Our Lady of Hope serves as the school's educational and spiritual leader. The Headmaster 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 will be the ambassador for the school to current and prospective families. The Headmaster serves as the leader of the school and its operations. This position reports to the Board of Directors and is supported by operations and academic staff for the overall success of the school.

Mission and Vision

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.

Job Duties:

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

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

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

Skills and Qualifications:

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: [email protected]

Upon receipt, you will receive a short questionnaire enabling you to provide greater detail of your educational vision, experience with Catholic classical education, and some areas of student life. You will also need to provide a Letter of Support from your Pastor detailing your active and engaged practice of your Catholic Faith.