Chesterton Academy of Our Lady of Guadalupe
July 12, 2021
21400 S. Nunneley Rd, Clinton Twp, Michigan
Job Type


Headmaster - Chesterton Academy of Our Lady of Guadalupe

About Chesterton Academy

Chesterton Academy is a joyful, pro-family and independent high school offering an integrated, classical 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.

Administrative Model

The Headmaster and the Executive Director lead the administrative team at Chesterton Academy. This model of school administration is one of equality and consensus with both specific and shared responsibilities.

The Headmaster is responsible for the instructional leadership of the school, as well as hiring and supervision of faculty, the curriculum, and student life.

The Executive Director is responsible for the business aspects of the administration including budgeting and finances, human resources, fundraising, strategic planning, public relations, building facility and is the key liaison to the Board of Directors.

These co-leaders share responsibilities for nurturing and maintaining the mission and traditions of the school, and ensuring fidelity to the Magisterium. Both administrators are hired by and report directly to the Board of Directors.

Position Requirements

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 faculty, student life, discipline and related parent communication.

The Headmaster must be practicing Roman Catholic, possess the minimum of a Master's Degree in Administration or related field, and demonstrate a commitment to Catholic secondary education. Salary is competitive and commensurate with experience.

Primary Responsibilities and Duties

Curriculum and Academic Excellence

Oversee adherence to curriculum and oversee changes

Collect course materials for each class (syllabus, weekly teaching plan, tests)

Review results of student tests (PSAT, ACT, SAT) and make curriculum changes as needed

Oversee school accreditation process and renewal


Oversee faculty hiring, evaluation, rehires, terminations
Conduct classroom observations for faculty members as part of evaluation process

Student Life and Discipline

Ensure discipline policies are enforced, communicated
Oversee parent-led sports and extracurricular activities
Ensure effectiveness of virtue house and faculty mentor programs
Oversee academic and behavioral eligibility for extra-curricular activities

Parent Communications

Send weekly Headmaster Missive to parents
Meet with parents regarding student discipline and academic issues


Admit new students upon review of placement exam, student application materials, and meeting
Oversee transfer student process (curriculum, regulations, forms, financial)
Review placement tests and contact parents with remedial needs
Deliver presentations to prospective parents and students at selected school events


Coordinate standardized testing, college applications and transcript preparation
Communicate with colleges, universities and other post-high school programs
Promote various vocational opportunities

Other School Operations

Oversee selection and evaluation of vendors (software, textbooks, other services)

Teaching Responsibilities (as needed)


The Headmaster maintains the following working relationships:

1. The Headmaster reports directly to the Board of Directors.

2. The Headmaster maintains a consultative, collaborative relationship with the Executive Director.

3. The Headmaster maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean, Academic Dean, and Athletic Director.

Minimal Requirements

Education: Masters degree in Education or related field

Experience: Significant teaching experience in a classical school environment; previous experience in secondary school administration; familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.

The candidate must be a practicing Catholic and willing to take the Oath of Fidelity to the Magisterium.

Certification: Not required Last Updated: June 22, 2021

Application Process and Deadline

Please submit a resume or curriculum vitae, a portfolio of related work samples, and an educational/leadership philosophy statement via email to by July 20th or until the position is filled.

Specific Job Functions and Responsibilities:

The Headmaster shall:

1.Establish and promote high standards and expectations for all students and staff for academic performance and responsibility for behavior.
2.Manage, evaluate and supervise effective and clear procedures for the operation and functioning of the school consistent with the philosophy, mission, values and goals of the school including instructional programs, extracurricular activities, discipline systems to ensure a safe and orderly climate, building maintenance, program evaluation, personnel management, office operations, and emergency procedures. Ensure compliance with all laws, board policies and civil regulations.
3.Establish the annual master schedule for instructional programs, ensuring sequential learning experiences for students consistent with the school's philosophy, mission statement and instructional goals.
4.Supervise the instructional programs of the school, evaluating lesson plans and observing classes (teaching, as duties allow) on a regular basis to encourage the use of a variety of instructional strategies and materials consistent with research on learning and child growth and development.
5.Establish procedures for evaluation and selection of instructional materials and equipment, approving all recommendations. Supervise in a fair and consistent manner effective discipline and attendance systems with high standards, consistent with the philosophy, values, and mission of the school. Ensure a safe, orderly environment that encourages students to take responsibility for behavior and creates high morale among staff and students. File all required reports regarding violence, vandalism, attendance and discipline matters.
6.Establish a professional rapport with students and with staff that has their respect. Display the highest ethical and professional behavior and standards when working with students, parents and school personnel. Serve as a role model for students, dressing professionally, demonstrating the importance and relevance of learning, accepting responsibility, and demonstrating pride in the education profession. Encourage all teachers to do the same.
7.Notify immediately the Board, and appropriate personnel and agencies when there is evidence of substance abuse, child abuse, child neglect, severe medical or social conditions, potential suicide or students appearing to be under the influence of alcohol or controlled substances.
8.Keep the Board advised of employees not meeting their contractual agreement.
9.Research and collect data regarding the needs of students, and other pertinent information including the collection of detail regarding the sacraments students have received or are preparing for. Keep the Chaplain informed of this information.
10.Keep the faculty informed and seek ideas for the improvement of the school. Conduct scheduled faculty meetings.
11.Develop clearly understood procedures and provide regular drills for emergencies and disasters.
12.Maintain a master schedule to be posted for all teachers.
13.Establish schedules and procedures for the supervision of students in non-classroom areas (including before and after school).
14.Maintain visibility with students, teachers, parents and the Board.
15.Communicate regularly with parents, seeking their support and advice, so as to create a cooperative relationship to support the student in the school.
16.Complete in a timely fashion all records and reports as requested by the Board.
17.Maintain accurate attendance records.
18.Communicate with the Board regularly about the needs, successes and general operation of the school.
19.Establish procedures for safe storing and integrity of all public and confidential school records. Ensure that student records are complete and current.
20.Protect confidentiality of records and information gained as part of exercising professional duties and use discretion in sharing such information within legal confines.
21.Organize and supervise procedures for identifying and addressing special needs of students including health-related concerns, and physical, emotional and spiritual needs.
22.Supervise the exclusion from school of any pupil who shows departure from normal health, who has been exposed to a communicable disease, or whose presence may be detrimental to the health and cleanliness of other pupils. Assure that excluded pupil's parents or guardian are apprised of the reasons for exclusion.
23.Maintain positive, cooperative and mutually supportive relationships with faculty, staff, and parents.
24.Attend required committee meetings (e.g.: fund-raising, curriculum, etc.) and extra school sponsored functions and religious events.
25.Perform any duties that are within the scope of employment and certifications, as assigned by the Board and not otherwise prohibited by law or in conflict with contract.
26.Provide quarterly student grade and behavior reports to parents. Post honor roll lists each quarter.
27.Nurture both students and teachers to achieve their greatest potential academically, instructionally and spiritually.
28.Maintain in the school a spirit conducive to prayer and study.
29.Provide an atmosphere of piety, obedience and charity throughout the school day.
30.Enforce 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.
31.Provide and supervise a safe recreation period for students.

About the Employer

Inspired by Saint Pope John Paul II, we take as our motto Cultura Vitae, the culture of life. We make it our mission to prepare our students to triumph over the materialism and despair that pervade our culture and to accept our Lord's offer to have life and have it abundantly. Our classical curriculum combines a broad, liberal arts education with a strong emphasis on the development of Christian virtues and an appreciation of beauty.

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