Assistant Head of School

Bennett Day School•Chicago, IL

13h•Onsite

About The Position

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, the school emphasizes real-world, project-based learning and aims to nurture inquiry, curiosity, creativity, and lifelong learning. Its campus is at 955 W. Grand Ave. The school is accredited by Cognia and NIPSA. 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. The role partners with Division Directors to strengthen academic coherence, support faculty growth, and lead strategic initiatives. While the Head of School leads growth, enrollment, marketing, and business operations, the Assistant Head focuses on the academic program and helps advance the Upper School’s identity and opportunities, including internships, athletics, and innovative assessment and learning. The Assistant Head reports to the Head of School and works closely with Division Directors, the Athletic Director, faculty, and enrollment, marketing, and business teams. Division Directors retain responsibility for daily division leadership, including faculty supervision and evaluation, student support, and family relationships. The Assistant Head directly oversees designated initiatives, including the Upper School internship program and the school’s work with the Mastery Transcript Consortium, and leads initiatives delegated by the Head. The role exercises judgment within agreed areas of responsibility; significant personnel, budgetary, policy, and organizational decisions are brought to the Head for approval. This is a full-time, 12-month position located at Bennett Day School in Chicago. The start date is July 1, 2027.

Requirements

Master’s degree in educational leadership or a related field.
At least ten years of teaching experience, including significant Upper School education and student culture 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, 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.
Trustworthy and discreet, with the ability to hold confidences and exercise sound judgment.
Commitment to the school’s mission and enthusiasm for hands-on, purposeful, individualized learning.
Emotional intelligence, including the ability to stay steady under pressure and handle difficult conversations with empathy and self-awareness.
Strong listening skills and ability to help others feel understood.
Visible and approachable presence in classrooms and at events with students, families, and colleagues.
Organization and steadiness in managing multiple priorities.
Respect for teaching and the children served.
Collaborative, non-prescriptive leadership that builds shared ownership.
Ability to give honest feedback with care.
Culturally responsive and inclusive approach that values diverse perspectives, identity, and belonging.
Systems-thinking ability to understand how people, programs, and processes connect.
Entrepreneurial approach to developing new ways of doing things.
Flexibility and adaptability as needs and priorities change.

Nice To Haves

Familiarity with Cognitive Coaching, restorative practices, or systems thinking.
Comfort with technology and AI tools that help a leadership team work more effectively.
Experience with inquiry-based or Reggio-inspired learning.
Experience with learning differences, executive functioning, and student support.
A good sense of humor, lightness, and perspective.

Responsibilities

Translate 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 informed of emerging issues and opportunities.
Prepare analysis and briefings for the Head of School, CEO, and board.
Coordinate leadership team meetings and the school’s annual calendar of 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, increasing student 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 promote a consistent, high-quality educational program.
Partner with Division Directors to foster an inclusive and equitable learning environment where students and families experience 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 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 onboarding and mentoring of new faculty.
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.