Headmaster
Our Lady of the Sacred Heart Academy Chesterton School
Rockford, IL
Job ID#:
4566176888
Posted:
August 14, 2026
Expires:
October 13, 2026
Category:
Secondary Education
Terms:
Full-Time Employee
Experience:
0-2 Years
Education:
Undergraduate Degree
Base Pay:
Salary
Send applications or inquiries to: YWRtaW5Ab2xzaGEub3Jn
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Job Description
Administrative ModelThe Headmaster and the Executive Director lead the administrative team at Our Lady of the Sacred Heart Academy-Chesterton Network School. This model of school administration is one of equality with both specific and shared responsibilities.
The Headmaster is responsible for internal operations, including the instructional leadership of the school, as well as hiring and supervision of instructional personnel, the curriculum, and student life.
The Executive Director is responsible for the business aspects of the administration including finances, human resources, fundraising, strategic planning, public relations, and building facility.
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.
Summary
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 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 Our Lady of the Sacred Heart Academy-CNS. A collaborative relationship between the Headmaster and Executive director is a requirement. 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.
Primary Responsibilities and Duties
Curriculum and Academic Excellence
• Oversee adherence to curriculum
• Oversee implementation of changes to curriculum
• Review results of student tests (IOWA, CLT, PSAT, ACT, SAT)
• Oversee school accreditation process and renewal per Network guidelines
Instruction
• 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 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 or school newsletter
• Develop and send monthly calendars and Reports
• Meet with parents regarding student discipline and academic issues
Admissions
• 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
Guidance
• 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)
Relationships
The Headmaster maintains the following working relationships:
• The Headmaster reports directly to the Board of Directors.
• The Headmaster maintains a consultative, collaborative relationship with the Executive Director.
• The Headmaster maintains a supervisory relationship with faculty and other selected staff, including Administrative Dean and Academic Dean.
Requirements
Education:
Masters in Education or related field
Experience:
Significant teaching experience in a classical school environment; previous experience in elementary or secondary school administration; familiarity with the mission of the Academy and the teachings of the Catholic Church; and working knowledge of institutional advancement/fundraising.
Certification:
Not required
About Our Lady of the Sacred Heart Academy-pre-K-12 and CSN High School
Founded in 2000 as a result of a grass-roots movement of parents, Our Lady of the Sacred Heart Academy's high school became a member of the Chesterton Schools Network in 2020. We offer a rigorous, integrated classical program for grades pre-K-12 and our curriculum is 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 OLSHA-CNS at www.olsha.org and the growing national Chesterton Schools Network at www.chestertonschoolsnetwork.org.
Send applications or inquiries to: YWRtaW5Ab2xzaGEub3Jn