Assistant Head of School

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

Description

Assistant Head of School

About Bennett Day 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.

Role Purpose

The Assistant Head of School serves as chief of staff to the Head of School and provides schoolwide 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.

Leadership Authority and Collaboration

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.

Core Responsibilities

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 schoolwide 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 schoolwide 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 program.
• Partner with Division Directors to foster an inclusive and equitable learning environment where students and families experience a strong sense of belonging and diverse identities and perspectives are reflected in the curriculum and school culture.
• Help shape humane, restorative approaches to student community and conduct that reflect Bennett's mission and values.

Faculty Growth and Culture

Partner with Division Directors to:

• Coordinate and strengthen the schoolwide faculty professional growth cycle, including coaching, observation, and feedback.
• Design and implement meaningful professional development opportunities, including culturally responsive teaching and inclusive practices, and support the onboarding and mentoring of new faculty.
• Contribute to faculty hiring, retention, and a positive, collaborative school culture.

Schoolwide Operations and Reporting

• Support the effective coordination of school systems, including schedules, events, and the school calendar.
• Help manage required reporting and accreditation processes, including Cognia and NIPSA accreditation and NAIS data reporting.
• Act on behalf of the Head of School in her absence when asked.

Requirements

Qualifications and Experience

Required

• Master's degree in educational leadership or a related field.
• At least ten years of teaching experience, including significant experience in Upper School education and student culture.
• At least five years in a formal leadership role in an independent or comparable school.
• Experience with project-based learning.
• An 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, with experience applying culturally responsive practices in teaching, leadership, and school community building.
• Exceptional organization and follow-through across multiple projects and priorities.
• Excellent written and verbal communication skills and sound judgment with confidential information.
• Familiarity with Cognitive Coaching, restorative practices, or systems thinking.
• Comfort with technology and AI tools that help a leadership team work more effectively.

Preferred

• Experience with inquiry-based or Reggio-inspired learning.
• Experience with learning differences, executive functioning, and student support.

Qualities We Are Looking For

• Trustworthy and discreet. Holds confidences and exercises sound judgment.
• Committed to our mission. Excited by hands‑on, purposeful, one‑of‑one learning.
• Emotionally intelligent. Reads a room, stays steady under pressure, and handles difficult conversations with empathy and self‑awareness.
• A good listener. Listens first, hears what people need, and makes them feel understood.
• Present and approachable. Shows up in classrooms and at events, and is known by students, families, and colleagues.
• A good sense of humor. Brings lightness and perspective and can laugh with the team.
• Organized and steady. Keeps many things moving without unnecessary drama.
• A teacher at heart. Respects the craft of teaching and the children we serve.
• Collaborative and non‑prescriptive. Builds shared ownership rather than issuing directives.
• Warm and direct. Gives honest feedback with care.
• Culturally responsive and inclusive. Values diverse perspectives, recognizes the importance of identity and belonging, and works to create a school community where every student, family, and employee feels respected and valued.
• Systems thinker. Sees how people, programs, and processes connect.
• Entrepreneurial. Thinks outside the box and builds new ways of doing things.
• Flexible and adaptable. Adjusts well as needs, priorities, and circumstances change.

Details and How to Apply

Location: Bennett Day School, 955 W. Grand Ave., Chicago (Fulton Market)
Start date: July 1, 2027 (full-time, 12-month position)
Benefits:

• Paid time off
• health, dental, and vision insurance
• short-term and long-term disability and life insurance
• transit, HSA, and FSA options
• 401(k) with employer match
• and a tuition benefit for children who attend Bennett Day School

To apply: Please submit a cover letter, resume, educational leadership philosophy, and five references to Heidi Hutchison at [e-mail] by November 6, 2026.

Bennett Day School is an equal opportunity employer and welcomes applicants of all backgrounds.