Careers at Chesterton

As a new school opening in August 2026 with 9th grade — and possibly 10th grade, depending on interest — our faculty will have a unique opportunity to grow and develop within our vibrant school community.

We are actively recruiting for our inaugural headmaster. All teaching positions will be open soon. Please follow us on social media (LinkedIn, Facebook, and Instagram) and check CatholicJobs.com regularly for posted opportunities.

Headmaster - open until filled

The Headmaster serves as the educational leader, responsible for managing the policies, regulations, and procedures to ensure that all students are supervised in a safe, learning environment that adheres to our Catholic identity and meets the approved curricula and mission of the school. The Headmaster is responsible for the curriculum, instructional leadership of the school, hiring and supervision of instructional personnel, student life, discipline, and related parent communication.

The Headmaster must be a practicing Roman Catholic, possess the minimum of a Master's Degree in Administration or a related field, and demonstrate a commitment to Catholic secondary education. Salary is competitive and commensurate with experience. The Board of Directors appoints the Headmaster of Chesterton Academy. A collaborative relationship between the Headmaster and Executive Director is required.

In addition to any teaching responsibilities, the duties of the Headmaster include:

1. curriculum and academic excellence

2. instruction

3. student life and discipline

4. parent communications

5. student admissions

6. guidance

7. other school operations.

For the full job description, see our posting on Catholicjobs.com.

Send applications or inquiries to: info@chestertonblcarlo.org

Teaching Positions - Opening Soon!

Full- and part-time teaching positions will be available across multiple disciplines, including:

• Mathematics

• Science

• Humanities (Theology, History, Literature, Latin, Philosophy)

• Fine Arts, Music, and Drama