Assistant Head of School

Bennett Day School Inc • Chicago, IL

4h • Onsite

About The Position

The Assistant Head of School serves as chief of staff to the Head of School and provides academic leadership across Early Childhood through grade 12. Working in close partnership with the Head of School and Division Directors, this senior leader strengthens academic coherence, supports faculty growth, and leads strategic initiatives aligned with Bennett Day School’s mission. The role focuses primarily on the academic program while coordinating with enrollment, marketing, and business teams and maintaining a visible presence in classrooms, at school events, and with internship employers and community partners.

The Assistant Head supports the continued growth and identity of the Upper School, including its academic programming, internships, athletics, community partnerships, and approaches to assessment and learning. The position directly oversees designated initiatives such as the Upper School internship program and the school’s work with the Mastery Transcript Consortium, and leads other initiatives delegated by the Head of School. Division Directors retain responsibility for daily divisional leadership, including faculty supervision and evaluation, student support, and family relationships. The Assistant Head exercises judgment within agreed-upon areas and brings significant personnel, budgetary, policy, and organizational decisions to the Head of School for approval.

The position reports to the Head of School and works closely with Division Directors, the Athletic Director, faculty, and the enrollment, marketing, and business teams. It also supports school systems, reporting, and accreditation, and may act on behalf of the Head of School when asked.

Requirements

• 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.
• 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.

Nice To Haves

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

Responsibilities

• Turn the Head of School’s strategic priorities into plans with clear owners and timelines, and track progress.
• Lead schoolwide initiatives on behalf of the Head of School from planning through completion.
• Coordinate across Division Directors and growth and business teams, keeping the Head of School informed of emerging issues and opportunities.
• Prepare analysis and briefings for the Head of School, CEO, and board.
• Coordinate leadership team meetings and the annual calendar of school priorities.
• Partner with the Middle and Upper School Division Director to support Upper School growth, including enrollment, academic programming, and community partnerships.
• Manage the Upper School internship program, including employer relationships, student placements, and connections between classroom learning and real-world experiences.
• Lead the school’s work with the Mastery Transcript Consortium, including mastery-based transcripts and learning records documenting student growth and achievement.
• Partner with the Athletic Director to strengthen and expand athletics and student opportunities for participation, competition, and school spirit.
• 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 to provide students with a consistent, high-quality educational program.
• Partner with Division Directors to foster an inclusive and equitable learning environment and ensure diverse identities and perspectives are reflected in the curriculum and school culture.
• Help shape humane, restorative approaches to student community and conduct that reflect the school’s mission and values.
• Coordinate and strengthen the schoolwide faculty professional growth cycle, including coaching, observation, and feedback, in partnership with Division Directors.
• Design and implement professional development, including culturally responsive teaching and inclusive practices, and support new faculty onboarding and mentoring.
• Contribute to faculty hiring, retention, and a positive, collaborative school culture.
• Support 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.

Benefits

• Paid time off.
• Health, dental, and vision insurance.
• Short-term and long-term disability insurance.
• Life insurance.
• Transit, HSA, and FSA options.
• 401(k) with employer match.
• Tuition benefit for children who attend Bennett Day School.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior