Assistant Head of School — Academic Innovation & Growth

Bennett Day School, Inc.; Chicago (IL); On-site; USD 90,000 - 150,000; Full time

Benefits offered by this job

Paid time off

Health, dental, and vision insurance

Disability and life insurance

Transit, HSA, and FSA options

401(k) with employer match

Tuition benefit

Job summary

Bennett Day School in Chicago seeks an Assistant Head of School to serve as chief of staff to the Head of School and provide schoolwide academic leadership for PreK–12.

You will partner with Division Directors, oversee academic coherence, support faculty growth, and lead strategic initiatives aligned with Bennett's mission in a 100,000-square-foot campus. This senior role emphasizes internships, Mastery Transcript work, and a strong collaboration with athletic and enrollment teams.

Qualifications

• Master's degree in educational leadership or related field.
• At least ten years of teaching experience, including significant Upper School experience.
• At least five years in a formal leadership role in an independent or comparable school.
• Experience with project-based learning.
• Understanding of competency-based assessment.
• Experience building or supporting an Upper School internship or experiential learning program.
• Experience supervising, coaching, and evaluating faculty.
• Demonstrated commitment to diversity, equity, inclusion, and belonging.
• Excellent written and verbal communication, organization, and judgment.
• Familiarity with Cognitive Coaching, restorative practices, or systems thinking.
• Comfort with technology and AI tools that help a leadership team work more effectively.

Responsibilities

• Turn the Head's strategic priorities into clear plans with owners and timelines.
• Lead schoolwide initiatives on behalf of the Head from planning through completion.
• Coordinate across divisions and growth teams; brief the Head on opportunities and issues.
• Prepare analysis and briefings for the Head, CEO, and board.
• Coordinate leadership team meetings and the school calendar of priorities.
• Support Upper School growth, enrollment, academic programming, and community partnerships.
• Oversee the internship program and Mastery Transcript Consortium work.
• Partner with the Athletic Director to strengthen the athletic program and student participation.
• Strengthen curriculum alignment, project-based learning, assessment practices, and instructional innovation.

Skills

Strategic leadership

Project-based learning

Diversity & inclusion

Communication

Education

Master's degree in educational leadership

Tools

Cognitive Coaching

Restorative practices

Systems thinking

Google Workspace / MS Office

Job description

Bennett Day School in Chicago seeks an Assistant Head of School to serve as chief of staff to the Head of School and provide schoolwide academic leadership for PreK–12.

You will partner with Division Directors, oversee academic coherence, support faculty growth, and lead strategic initiatives aligned with Bennett's mission in a 100,000-square-foot campus. This senior role emphasizes internships, Mastery Transcript work, and a strong collaboration with athletic and enrollment teams.