Head of Upper School

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. 

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.

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