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Head of Upper School

Job in Pepper Pike, Cuyahoga County, Ohio, USA
Listing for: Heritage Classical Academy
Full Time position
Listed on 2026-03-10
Job specializations:
  • Education / Teaching
    Christian / Catholic School, Education Administration
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

Job Summary:Heritage Classical Academy (HCA) seeks a faithful, mission-drivenHead of Upper Schoolto 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.

Biblical Expectations:All employees of Heritage Classical Academy possess a Christian testimony demonstrating a personal, active, and growing relationship with Jesus Christ. They also fully support HCA’s Statement of Faith and support the mission to Cultivate Lifelong Learners Who Think and Live for Christ.

They will also be involved in a local church that aligns with the mission and vision of HCA.

  • 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
  • Completeotherduties 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
  • Experience teaching and leading in a school setting; classical Christian experience strongly preferred
  • Strong communication, organizational, and leadership skills

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 Pikeand 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:Interested applicants should submit a resume and cover letter by clicking "Apply for This Job" to begin the application process.

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