Upper School Head (7th-12th)

The Covenant School; Indianapolis (IN); On-site; USD 75,000 - 100,000; Full time

Job summary

The Covenant School in Indianapolis is looking for an experienced Dean of Upper School (grades 7–12) to oversee faculty leadership and academic quality. This role not only involves administrative oversight but also includes teaching a class to stay connected with students.

The ideal candidate will have strong organizational skills, understand the challenges of a growing Upper School, and embrace a classical, Christian educational model. This position is critical for shaping the future of the Upper School.

Qualifications

• Experience as an Upper School administrator.
• Ability to lead operationally and academically.
• Understanding of classical, Christian education.

Responsibilities

• Oversee Upper School faculty and academics.
• Manage graduation requirements and college advising.
• Evaluate teacher performance and oversee onboarding.

Skills

Strong organizational skills

Operational leadership

Administrative tenacity

Collaboration

Strong systems-thinking

Job description

The Classical Academy in Indianapolis is seeking an experienced Upper School leader to serve as Dean of Upper School (grades 7–12), functioning essentially as the Head of Upper School within our leadership structure.

Founded in 2018, The Classical Academy is a growing classical, Christian, collaborative school serving nearly 330 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, 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. The Dean of Upper School will also teach at least one class each year in order to remain connected to students and classroom life.

This is a unique opportunity to help shape the next chapter of Upper School life and leadership within a thriving and rapidly growing classical Christian school.