Head of School Chesterton Academy of The Holy Family Joyfully Catholic High Scho

Position Summary: The Head of School at Chesterton Academy of The Holy Family will serve as the educational and administrative leader, responsible for realizing our educational philosophy, fostering a positive school culture, ensuring academic excellence, and promoting the spiritual development of our students. This role involves close collaboration with the Board of Directors, faculty, staff, and parents to uphold the school’s mission. The Head of School reports to the Board of Directors.

Opportunities and Challenges: The Head of School, in collaboration with the Board of Directors, will play a key role in building a sense of community among staff, students, parents, alumnae, and benefactors. Specific opportunities and challenges include:

Collaborating with the Board of Directors on a strategic plan;

Ensuring alignment with the Chesterton Academy identity and Chesterton Schools Network standards;

Fostering an environment that embodies the Catholic faith and virtues;

Fully understand, articulate, and integrate the history of CATHF, its mission and academic vision both internally and externally;

Overseeing and promoting high standards and expectations for all students and employees;

Partnering with the Business Operations Team and the Board of Directors to maintain and enhance the financial strength and stability of CATHF;

Inspiring the CATHF community; staff, students, parents, alumnae, and benefactors to embrace and support the mission of the school and the fundraising efforts to fund operations, facility improvements and to increase scholarship awards.

Key Responsibilities:

Educational Leadership:

Articulate the academic vision consistent with the school’s mission and CSN;

Promote fidelity to the CSN curriculum, emphasizing critical thinking across disciplines;

Foster an environment that encourages knowledge pursuit, intellectual curiosity, and a love of learning;

Inspire students by joyfully practicing the Catholic faith;

Oversee the implementation of the CSN curriculum, in collaboration with the Dean of Curriculum and Instruction.

Administrative Oversight:

Collaborate with the Board of Directors to set strategic goals and priorities;

Recruit and retain devoted and mission-driven faculty and staff;

Lead and support the faculty and staff, providing professional development and fostering a collaborative culture;

Manage day-to-day operations, including budgeting, resource allocation, and facility management;

Ensure compliance with education laws, regulations, and accreditation standards.

Spiritual and Moral Formation:

Promote the Catholic faith and the school’s commitment to spiritual formation;

Foster a faith-filled, joyful culture that encourages spiritual growth and community;

Encourage a culture of respect, virtue, and integrity among students, families, and employees;

Support and oversee the implementation of the St. John Bosco discipline methods.

Parent and Community Engagement:

Ignite support for classical education among parents, employees, and stakeholders;

Build strong relationships with parents, alumnae, and the local community;

Engage parents in the educational process and involve them in school activities;

Communicate effectively with stakeholders, providing regular updates on school activities and achievements.

Enrollment, Development, and Marketing:

Collaborate with the Admissions Team to attract and retain students aligned with the school’s mission;

Participate in marketing and outreach efforts to promote the school within the community;

Support development and build strong donor relationships.

Qualifications:

Joyful, practicing Catholic with an active and integrated faith life;

Knowledge of classical education principles and practices;

Ability to inspire and motivate various stakeholders on the mission;

Highly relational leader with strong emotional intelligence and community-building skills;

Strong communication and interpersonal skills, with the ability to share the school’s story effectively;

Working knowledge of institutional advancement and fundraising;

Experience in secondary school teaching or administration, preferably in a classical school;

Bachelor’s degree required, Master’s or PhD preferred;

Experience in other industries is beneficial.

Application Process: Interested candidates are asked to reflect on the Chesterton Academy of The Holy Family mission before applying. If, after prayerful consideration, an applicant believes they can support and embrace the mission of the school, they are to complete and submit the following via the school website:

A completed candidate questionnaire;

A cover letter expressing their position of interest;

A current resume;

An essay responding to the prompt: “Having reflected on Chesterton Academy of The Holy Family’s mission, explain in what specific ways you anticipate supporting and advancing our school’s mission.”;

A list of five professional references with names, relationships, phone numbers, and email addresses (references will not be contacted without the candidate’s permission).

The Board of Directors will uphold the confidentiality of our candidates until necessary to share with our school community.

Join us in shaping the future of Catholic classical education!

Please do not email resumes; use the link above or go to the school website.

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