Headmaster – Chesterton Academy of Milwaukee – Brookfield, WI


Mission Statement: Chesterton Academy of Milwaukee provides an integrated, classical education rooted in the Catholic intellectual tradition and centered on the Incarnation of Jesus Christ. In cooperation with parents, the school forms students in intellect and will so that they may flourish in virtue and lead lives dedicated to the greater glory of God.

Position Summary
This is a great opportunity for one called to leadership. Be part of the educational movement reintroducing the Catholic intellectual tradition. Chesterton Academy of Milwaukee is a part of the Chesterton Academy Network and opened in 2016.
We are looking for a commitment to classical, liberal arts curriculum. Appointed by the board of directors of Chesterton Academy of Milwaukee, Inc. The headmaster is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional and administrative personnel, the curriculum, and student life.

Position Overview
The headmaster serves as the educational and organizational leader and is responsible for implementing the network curriculum, managing the teaching staff, and the policies of Chesterton Academy of Milwaukee, Inc.

He or she is responsible for instructional leadership (teacher growth and development), curriculum and school recommendations, hiring and supervision of instructional personnel, student life, discipline, and all related parent communications.

The headmaster will ensure that students are in a learning environment to maximize both faith and reason, in order that they develop God-given talents and gifts and find joy in their ultimate calling. We seek to lead and transform through beauty, truth and goodness.

Specific Duties and Responsibilities:

1. Establish and promote high standards and expectations for all students and staff for academic performance and responsibility for behavior.
2. Establish a professional and respectful rapport with students and staff. Displays the highest ethical and professional behavior and standards when working with students, parents, and school personnel.
3. Manage, evaluate and supervise effective and clear policies and procedures for the operation and functioning of the school that is consistent with the schools philosophy, mission, values and goals.
4. Supervises the instructional programs of the school, evaluating lesson plans and observing classes on a regular basis. Encourages the use of a variety of instructional strategies and materials.
5. Establish procedures for evaluation and selection of instructional materials and equipment, approving all recommendations.
6. Supervises in a fair and consistent manner effective discipline and attendance systems with high standards, consistent with the philosophy, values and mission of the school.
7. Ensures a safe, orderly environment that encourages students to take responsibility for behavior and creates high morale among staff and students.
8. Establishes schedules and procedures for the supervision of students in non-classroom areas.
9. Maintains safe storing and integrity of all public and confidential school records. Ensures that student records are complete and current.
10. Protect confidentiality of records and information gained as part of exercising professional duties and use discretion in sharing such information within legal confines.
11. Communicates with parents, seeking their support and advice, so as to create a cooperative relationship to support the student in the school.
12. Complete in a timely manner all records and reports as requested by the board.
13. Supervises procedures for identifying needs of students including academic, health- related, physical, emotional and spiritual needs.
14. Maintains an atmosphere of piety, obedience and charity throughout the school.
15. Enforces uniform policy and appearance policy so as to assure a school environment that is focused on group spiritual and academic achievement rather than on individuals.
16. Notifies the board of any contractual violations of staff.
17. Maintains visibility with students, teachers, parents and board. Attends required meetings and school sponsored events.
18. Delegates assignments to administrative personnel as appropriate.
19. Demonstrates strong leadership skills in exercising duties and responsibilities.

We are located in the beautiful town of Brookfield, WI, a suburb of Milwaukee.
Chesterton Academy of Milwaukee is a member of the Chesterton Schools Network (Edina, Minnesota).


Education: Masters in Education or knowledge of classical, liberal education preferred.

Experience: Teaching experience, secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church.

Must be a practicing Roman Catholic in good standing. Demonstrates a commitment to Catholic secondary education.

Salary is competitive and commensurate with experience.

We are a classical high school, the ability and desire to teach in a variety of disciplines is considered an asset. Please state the disciplines that you are qualified to teach and any co-curricular sports, clubs or activities that you are competent to coach, supervise or organize.


Apply by sending a cover letter and resume to: Bonnie Zamorski at bzamorski@chestertonmke.org or Chesterton Academy of Milwaukee, P.O. Box 1686, Brookfield, WI 53008-1686. We will not be able to respond individually to each resume, but we will contact you soon should we have a position that matches your qualifications. Please visit our website at: chestertonmke.org.