Lakeside School

On Feb. 11, Dr. Kai Bynum shared with the Lakeside community that he will be stepping down as Lakeside’s head of school in order to focus on his health. “Serving as Lakeside’s head of school has been a remarkable privilege,” shared Bynum. “Even as I found the work deeply fulfilling and invigorating, the demands of serving as head were proving incompatible with the realities of my health.” Bynum has been on medical leave since November 2025.

"In his four years at Lakeside, Kai Bynum has had a notable impact on the school," wrote Board of Trustees Chair Sean O'Donnell, in his message to the community. "Under [Kai's] leadership and with the help of a stellar leadership team, the school has responded to the world-altering advent of generative AI; modernized its approach to campus safety; expanded programming that supports student and family health and wellbeing; and overseen major advancements in educational excellence, including the construction of the Vassar Center, our new home for sciences and humanities. Perhaps most importantly, Kai led our community through Lakeside’s first comprehensive strategic planning process in 20 years, uniting the school’s work in educational excellence; community experience, engagement, and impact; and infrastructure, operations, and capacity. Led by Kai and the trustees, the school reaffirmed Lakeside’s mission and values; recommitted to diversity, equity, inclusion, and belonging; and adopted a vision that has inspired us all with a sense of purpose, possibility, and hope."

This spring, the Board of Trustees will launch a comprehensive search for Lakeside School’s next head of school, who will start in the summer of 2027. Bynum will continue to work with the board in an advisory capacity while the school navigates the head of school transition.

During the search, Assistant Head of School/Upper School Director Ryan Boccuzzi will step into the role of interim head of school, ensuring stability and continuity. He will be working closely with Lakeside’s directors, particularly Associate Head of School/Chief Financial Officer Birage Tandon and Assistant Head of School/Director of Student and Family Support Jamie Asaka, ensuring that all aspects of the school continue to run smoothly.

“Later this year, we’ll have opportunities to personally express our gratitude and appreciation for Kai’s many contributions to our community,” shared Board Chair Sean O’Donnell ’90. “On behalf of the board, I want to thank Kai for his vision, passion, and deep love and care for our community, and wish him peace and good health.”

Read the full announcement from Dr. Bynum and Lakeside School Board Chair Sean O’Donnell.