Assistant Head of School

Description

Assistant Head of School

Bennett Day School is a PreK–12 independent school in Chicago's Fulton Market neighborhood, serving more than 400 students from age two through grade 12. Founded in 2014, Bennett set out to build a "one-of-one" school where real-world, project-based learning builds resilience, creativity, and lifelong learners. Our nearly 100,000-square-foot campus at 955 W. Grand Ave. includes a full-size gymnasium, library, and community spaces.

Accredited by Cognia and NIPSA, Bennett was named a 2026 Chicago Innovation Awards Top 100 finalist for utilizing the Mastery Transcript in both Middle and Upper School.

Our mission: To provide a collaborative culture that nurtures our innate sense of inquiry and curiosity. We are committed to advancing creativity, innovation, and the development of lifelong learners and leaders.

The Assistant Head of School serves as chief of staff to the Head of School and provides school wide academic leadership from Early Childhood through grade 12. Partnering with Division Directors, the Assistant Head strengthens academic coherence, supports faculty growth, and leads strategic initiatives that advance Bennett's mission.

While the Head of School leads growth, enrollment, marketing, and the school's business side, the Assistant Head focuses on the academic program. Together with the Head, the Assistant Head is out and about: in classrooms, at games and exhibitions, and with the internship employers and community partners who make Bennett's real-world learning possible.

The Assistant Head also plays a significant role in the Upper School's continued growth, helping shape its identity and expand opportunities for students through internships, athletics, and innovative approaches to assessment and learning.

Reports to: Head of School
Works closely with: Division Directors, Athletic Director, faculty, and the enrollment, marketing, and business teams.

The Assistant Head is a senior academic leader who works in close partnership with the Head of School and Division Directors. The role requires both independent leadership and a collaborative approach that respects the expertise and responsibilities of existing school leaders.

• Division Directors retain responsibility for the daily leadership of their divisions, including faculty supervision and evaluation, student support, and family relationships.
• The Assistant Head directly oversees designated initiatives, including the Upper School internship program and Bennett's work with the Mastery Transcript Consortium, and leads initiatives delegated by the Head of School.
• Decisions: The Assistant Head exercises judgment within agreed-upon areas of responsibility and brings significant personnel, budgetary, policy, and organizational decisions to the Head for approval.

Chief of Staff to the Head of School

• Turn the Head's strategic priorities into clear plans with owners and timelines, and track progress.
• Lead school wide initiatives on the Head's behalf, from planning through completion.
• Coordinate across Division Directors and the growth and business teams so the Head is informed of emerging issues and opportunities.
• Prepare analysis and briefings for the Head, the CEO, and the board.
• Coordinate leadership team meetings and the school's annual calendar of priorities.

Program Growth and Student Experience

• Partner with the Middle and Upper School Division Director to support the continued growth of the Upper School, including enrollment, academic programming, and community partnerships.
• Manage and oversee the Upper School internship program, including employer relationships, student placements, and meaningful connections between classroom learning and real-world experiences.
• Lead the school's work with the Mastery Transcript Consortium, including mastery-based transcripts and the learning records that document student growth and achievement.
• Partner with the Athletic Director to strengthen and expand Bennett's athletic program, increasing opportunities for student participation, competition, and school spirit.

Academics and School Life

• Lead school wide efforts to strengthen curriculum alignment, project-based learning, assessment practices, and instructional innovation from Early Childhood through grade 12, in collaboration with Division Directors.
• Support coherence and collaboration across divisions so students experience a consistent, high-quality educational…