Head of School

Job Description

Summary
Chesterton Academy of St. Nicholas (CASN) is a new classical high school in the Catholic tradition opening up in the fall of 2026 in Northwest Indiana. Our mission is to raise the next generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. We are seeking our founding head of school who has a passion for Catholic classical education.

POSITION DETAILS
We are opening in fall 2026 with a freshmen and sophomore class. We anticipate enrolling 10 to 15 students in the first year and growing from there. We are finalizing a temporary location. We would like someone who can start in January on a stipend basis with plans to start full time in May or June 2026, following our planned vision dinner to raise a majority of our funds. The headmaster will work closely with the founding board to implement the Founders' vision.

Qualifications
Faithful, practicing Catholic in full communion with the Church
Willingness to take the Oath of Fidelity to the Magisterium
Bachelor's degree or higher (Master's in Educational leadership or related field preferred) Minimum of 3 years teaching experience (secondary education preferred) Prior administrative or leadership experience in education strongly desired.

Skills and Attributes
Proven history of being scrappy and frugal - we are a new school committed to providing a quality education to students while also operating within the confines of being a nonprofit. Strong leadership and interpersonal skills. Excellent verbal and written communication
Ability to form and mentor teachers and students. Sound judgment and managerial ability. Strong organizational and time-management skills. Capacity to take direction and collaborate effectively.
Engaging public speaker, comfortable addressing teens and parents
Deep personal prayer life and commitment to Catholic formation

Key Responsibilities
Curriculum and Academics
Oversee implementation of the Chesterton Schools Network curriculum. Monitor academic excellence and student achievement (CLT, PSAT, ACT, SAT). Manage accreditation and renewal processes in collaboration with CSN. Supervise faculty recruitment, evaluation, professional development, and retention. Conduct instructional improvement. Oversee student life and discipline. Communicate regularly with parents and the community.

Teaching
Teach up to three courses during the school's initial years
Compensation. Salary is competitive and commensurate with experience.

Application Process

Candidates should familiarize themselves with Chesterton Academy of the St. Nicholas and Chesterton Schools Network via www.nwicasn.com

Please send the following to: northwestindianaca@gmail.com
Cover letter
Resume
Three professional references. It is requested that at least one be from someone who is familiar with your spiritual life, such as a pastor or deacon. If this is not possible at the moment (i.e. you currently work at a Catholic school connected to your parish) please let us know.

About Chesterton Academy
Founded in 2008 as a result of a grass-roots movement of parents, Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, 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 and the growing national
Chesterton Schools Network (https://chestertonschoolsnetwork.org/).

About the Employer
Chesterton Academy of St. Nicholas is a member of the Chesterton Schools network. We are opening our school in August 2026.

About the Employer

Chesterton Academy of St. Nicholas is a member of the Chesterton Schools Network, which mission is to bring up the new generation of joyful leaders and saints.