Head of School Search

Site Visit on Feb 12-13 and Community Input

As we begin the search for our next Head of School, below is an update on the next steps.

Our Search Partner: As mentioned in our earlier announcement, the Board and I have retained Carney, Sandoe & Associates to lead this comprehensive search. We are pleased to share that our CS&A Consultant will be Chris Boyle, an expert in the field who has led more than seventy searches for educational leaders. As a former leader within the Chicago independent school community, Chris brings a deep understanding of our local landscape and a growing appreciation of the mission and unique value of Bennett Day School.

Consultant Site Visit: February 12-13: Building on the input gathered from the Community Survey, CS&A will conduct a comprehensive two-day site visit on Thursday, February 12, and Friday, February 13. During this visit, Chris Boyle will be on campus to experience the "Bennett Why" in action by touring campus, spending time in classrooms, and meeting with multiple groups and individuals to further inform the search profile and our next steps, including:

• Family Association Chairs: A gathering following morning drop-off to ensure parent/guardian perspectives are included.
• Faculty and Staff: Time before and after school to ensure faculty and staff perspectives are included.
• School Leadership and Administration: Multiple sessions with our leadership and administrative teams and individuals.
• Search Advisory Committee: A smaller group of faculty and staff (several of whom are also Bennett parents/guardians), to be selected by Jackie Miller to provide a comprehensive perspective across grade levels to inform the search.
• Search Committee of the Board: A session with the board search committee responsible for screening candidates with CS&A and making candidate recommendations to the board. I am supported on this committee by board members like Gail Ward, founding Principal of Walter Payton High School, and Betsy Morton, a human capital expert and former CHRO with an extensive background in education. We and CS&A will maintain strict confidentiality regarding candidates during the early screening process to ensure we attract the highest quality pool of leaders as well.

Read the full letter.

Planning for Bennett’s Future: Leadership Transition through 2026-2027

After seven years of serving as an administrator at Bennett Day School, I have decided that now is the right time for me to begin a thoughtful transition from my leadership of the school.

This decision comes after much reflection. I am incredibly proud of the journey we have shared and the strength of the community we have built together. Over the last seven years, we have worked to grow a solid and stable foundation for Bennett for years to come—including doubling our enrollment and faculty, and expanding our physical campus.

We have also stood together through the most challenging of times, from the pandemic to the loss of cherished community members as well.

Leading the school through this period of growth has been both deeply rewarding and demanding, requiring personal sacrifice along the way. As I began to reflect on the next chapter, it was important to me that any transition be approached thoughtfully and deliberately in a way that prioritizes the school’s continued success and honors the community and mission I care so deeply about.

Because I love Bennett, a goal for me is to ensure there is continuity in leadership. To that end, our Board and I have collaborated on a transition plan that will be smooth and that extends over the next year-and-a-half through June 2027. This approach prioritizes the long-term stability of our community.

Read the full letter.

Our Path Forward at Bennett

I want to share profound gratitude for Jackie Miller’s leadership and dedication over what will be an eight-year journey with Bennett through next school year. Jackie has shared a very thoughtful plan for a smooth transition from her role as Head of School over the next year-and-a-half with full alignment and support from our Board and me.

It is a priority to ensure there is continuity and continued momentum for the community we have built together. We are in a position of strength given that Jackie still serves as Head of School through 2025-2026 and then as a Senior Advisor through 2026-2027 to overlap her tenure with a new Head of School. This collaborative approach allows us to protect the "Bennett Why" while providing new leadership with deep institutional knowledge and a seamless transition over time.

Read the full letter.