CAREERS

Chesterton Academy is a school with a higher purpose. Our faith and family-centered mission uses a relevant, innovative classical curriculum with a strong Fine Arts emphasis. Daily Mass, reconciliation, student led prayer team, weekend retreats and a strong Pro-Life stance defines our Catholic Identity.

We are always looking for mission-driven individuals to help us raise up the next generation of saints. If you are seeking a teaching or administrative role, please send a resume to board@castserra.com.

Current Postings

Feb. 15, 2026

Headmaster | Full Time

The Headmaster serves as the educational leader of Chesterton Academy of St. Serra. This position is responsible for the instructional life of the academy, ensuring that all students are supervised in a safe, learning environment with policies, regulations, and procedures that adheres to our joyful, Catholic identity while guiding the approved curricula and meeting the mission of the school.

Executive Director | Full Time

The Executive Director serves as the business, operational, and advancement leader of Chesterton Academy of St. Serra. This position is responsible for the external life of the academy, ensuring that CASS operates with excellence in finance, fundraising, operations, human resources, facilities, enrollment, marketing, and strategic planning-all in fidelity to CASS's joyful Catholic mission.