Upper School Head
Listed on 2026-07-19
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Education / Teaching
Education Administration, Academic, School Principal
Position Description
The Classical Academy in Indianapolis is seeking an experienced Upper School Head (grades 7–12).
Founded in 2018, The Classical Academy is a growing classical, Christian, collaborative school serving nearly 330 PreK-12 students. Our Upper School is entering a significant new season of growth as double cohorts move steadily into grades 7–12, and we are seeking a mature, highly capable leader to help guide the division through this next chapter.
This is not primarily a student-life or discipline role. We are seeking a true divisional leader who carries broad responsibility for the operational and academic life of the Upper School, including faculty leadership, instructional quality, organizational systems, and execution. The ideal candidate will be an experienced Upper School administrator who understands the pace, complexity, and relational demands of a growing Upper School.
He or she should fully embrace a classical, Christian, university-schedule model and thrive within a collaborative leadership culture built around shared authority, trust, and strong partnership with families.
Responsibilities include overseeing Upper School faculty, academics, graduation requirements, transcripts, college advising, teacher onboarding and evaluation, and overall divisional systems and follow-through. The Dean also oversees the Assistant Dean of Upper School, who primarily focuses on House and student culture, while working closely with operations, administrative staff, college advisor, and the Head of School.
We are seeking someone who is highly organized, operationally strong, and able to lead through others with wisdom, steadiness, humility, and maturity. Strong systems-thinking, administrative tenacity, and excellent follow-through are essential.
This is a unique opportunity to help shape the next decade of Upper School life and leadership within a thriving and rapidly growing classical Christian school on the northeast side of Indianapolis.
* Highly competitive pay and a moving stipend
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