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Head of Upper School

Job in Pepper Pike, Cuyahoga County, Ohio, USA
Listing for: The Covenant School
Full Time position
Listed on 2026-02-16
Job specializations:
  • Education / Teaching
    Christian / Catholic School, Education Administration, Faculty, School Principal
Salary/Wage Range or Industry Benchmark: 150000 - 200000 USD Yearly USD 150000.00 200000.00 YEAR
Job Description & How to Apply Below
Location: Pepper Pike

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:

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