Head of Upper School

The Covenant School; Pepper Pike (OH); On-site; USD 70,000 - 90,000; Full time

Job summary

A classical Christian school is seeking a Head of Upper School to provide spiritual, academic, and cultural leadership for grades 6–12. This role requires a committed Christian leader who supports the school’s mission. Responsibilities include recruiting and mentoring faculty, overseeing student life and discipline, and fostering a joyful and engaged school culture. Applicants need a Bachelor’s degree and experience in a school setting, with strong communication and leadership skills emphasized. This position offers an opportunity to shape a spiritually rich educational environment in Pepper Pike, Ohio.

Qualifications

• Committed Christian with active membership in a local church.
• Experience teaching and leading in a school setting, preferably classical Christian.
• Strong interpersonal and relational abilities.

Responsibilities

• Provide spiritual, academic, and cultural leadership for grades 6–12.
• Foster a Christ-centered Upper School culture marked by joy and charity.
• Recruit, mentor, evaluate, and support Upper School faculty.

Skills

Strong communication

Organizational skills

Leadership skills

Proficiency in Microsoft Office

Education

Bachelor’s degree

Master’s degree

Job description

Overview

Job Summary: Heritage Classical Academy (HCA) seeks a faithful, mission-driven Head of Upper School to provide spiritual, academic, and cultural leadership for grades 6–12 in service of the school’s mission of Cultivating Lifelong Learners Who Think and Live for Christ. The Head of Upper School is a senior leader who understands and advances the vision of classical Christian education while upholding The Portrait of the Graduate as a guiding standard for student formation. This individual will shape Upper School culture, support faculty, shepherd students, and partner with families.

Mission & Leadership

• Advance and model HCA’s mission, vision, values, and Statement of Faith
• Foster a Christ-centered Upper School culture marked by joy, charity, order, and curiosity
• Uphold The Portrait of the Graduate as a shared expectation for faculty and students
• Demonstrate servant leadership and a biblical model of work
• Represent the school clearly and graciously to students, families, and the community

Faculty & Academic Leadership

• Recruit, mentor, evaluate, and support Upper School faculty
• Cultivate a culture of professional growth and Christian charity
• Support faithful classical pedagogy and curricular coherence
• Collaborate with senior leadership on staffing, scheduling, and course offerings

Student Life & Formation

• Oversee student life, discipline, and spiritual formation for grades 6–12
• Apply discipline biblically and restoratively, seeking growth and reconciliation
• Guide students toward maturity consistent with The Portrait of the Graduate
• Oversee the House System and support co-curricular programs
• Plan and implement vision for Convocation and Chapels, along with other programs
• Support college and career readiness

Administrative Responsibilities

• Oversee daily Upper School operations
• Communicate clearly and consistently with parents and faculty
• Interview prospective and current families to ensure mission alignment
• Partner on community engagement initiatives
• Complete other duties as assigned by the Associate Head of School

Qualifications

• Committed Christian with active membership in a local church
• Full support of HCA’s mission and Statement of Faith
• Bachelor’s degree required; Master’s degree preferred
• Experience teaching and leading in a school setting; classical Christian experience strongly preferred
• Strong communication, organizational, and leadership skills
• Proficiency in Microsoft Office

Personal Qualities

• Shepherd-hearted, humble, and joyful leader
• Wise, steady, and relational
• Ability to lead with clarity, consistency, and grace
• Capacity to manage conflict biblically and constructively
• Passion for forming students who think and live for Christ

About Heritage Classical Academy

Heritage Classical Academy is a classical Christian school, with campuses in Pepper Pike and Peninsula, Ohio, partnering with families to cultivate lifelong learners who think and live for Christ through a Christ-centered education grounded in truth, goodness, and beauty.

Application Process

Application Process: https://www.heritageclassicalacademy.org/employment