Dear Lakeside School parents and guardians, 

I’m writing today with bittersweet news. After many heartfelt conversations with my family, my medical team, and Lakeside’s trustees, I’ve made the hard decision to step down as Lakeside’s head of school. This has been an incredibly difficult choice to make, but I believe it is the right one, both for my family and me, but most especially for everyone at Lakeside. 

Serving as Lakeside’s head of school has been a remarkable privilege. We have made so much meaningful progress together: launching Lakeside’s strategic plan, Hope in Action; completing the T.J. Vassar ’68 Center for the Sciences and Humanities; and evolving the school’s approach to community health and safety. 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. As poet Theodore Roethke writes in “The Waking,” “I learn by going where I have to go.” During my leave, I turned the mirror of awareness and perspective on myself and realized what I needed to do; though the decision is a heavy one, it is accompanied by a sense of peace. 

I would not have been able to make this decision without the deep trust and respect I have for everyone at the school. Our kids — and all of us — deserve stability and certainty, especially given the challenges of the world right now. While I am no longer head of school and not involved in day-to-day operations, I am still working with the board in a more limited capacity, advising the school on strategic matters. Transitions are hard, but I will be supporting this one fully while the school conducts a search for a new head. I want to thank the trustees and my colleagues for their support as I came to this decision. 

This community has given me so much joy and care. Your children and their teachers truly have transformed my world and provided me with a powerful sense of hope for the future. Thank you. 

With gratitude, 

Kai Bynum 

Dear Lakeside School parents and guardians,

I write today to thank Kai Bynum for his inspired leadership as Lakeside’s head of school, and announce that Assistant Head of School/Upper School Director Ryan Boccuzzi will step into the role of interim head of school, starting today. This spring, we will commence a comprehensive search for Lakeside School’s next head of school, who will start in the summer of 2027. 

In his four years at Lakeside, Kai Bynum has had a notable impact on the school. Under his 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. 

Supporting our students in developing healthy bodies is a core part of Lakeside’s mission. While Kai’s decision to step down as head of school in order to prioritize his health is a difficult moment for him and Lakeside, we commend him for doing what we ask our students and each other to do: listen to your body; treat your health as something precious; and have the insight and courage to step off the playing field when your body needs you to do that. Our full board supports Kai on his path toward healing, and we are grateful that Kai will stay on in an advisory capacity to the board while we navigate this transition. 

We know that transitions and change, especially those that come on suddenly, can be unsettling. Yet there is much for which to be grateful: We have a solid foundation, a remarkable community, and a capable leadership team. And Lakeside’s future is bright. On April 23, we will officially open the T.J. Vassar ’68 Center for the Sciences and Humanities — the first new academic building at Lakeside in 40 years. Admissions applications are among the highest ever: Students and families from public, independent, and religious schools are eager to join our community. Generations of generous community support have enabled our robust financial aid program, meaning that students can come to Lakeside regardless of their ability to pay. That same remarkable support ensures that our faculty compensation is among the highest in the country. 

Most importantly, Lakeside’s faculty, staff, coaches, and administrators are exceptional: They develop students’ confidence and courage. They provide inspiration and instill hope. They create an environment where your students can become critical thinkers, risk-taking artists, and loyal teammates. The young people who graduate from Lakeside are kind, well prepared, and ready to make a difference in the world.

All of us, working together, make this school strong. Lakeside is a special place because of the people connected to and invested in this community.

Interim Head of School Ryan Boccuzzi: Ensuring stability and a smooth transition

Lakeside’s Board of Trustees’ priority is building on the school’s strength and ensuring that Lakeside remains a transformative educational community. To support that goal, Ryan Boccuzzi will serve as Lakeside’s interim head of school, ensuring stability, continuity, and a smooth transition to the next head of school. 

Many of you know Ryan through his role as assistant head of school/Upper School director. A seasoned and deeply collaborative school administrator, he leads from a place of heartfelt appreciation and understanding of faculty and teaching, and a focus on the academic, social-emotional, and developmental needs of students. Ryan 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. 

Ryan joined the Lakeside community as Upper School director in 2022 and was named assistant head of school in 2024. His leadership spans multiple institutions: He served as Upper School director at Brentwood School in Los Angeles and as director of Upper Schools at Rolling Hills Preparatory and Renaissance Schools in San Pedro, California. Ryan has a bachelor's degree from Colby College, and he holds a master’s in private school leadership from the Klingenstein Center at Columbia University’s Teachers College. As someone who started his career as a teacher, dean, and coach, Ryan understands the holistic nature of education and the developmental needs of kids throughout the middle and high school years. As Assistant Head of School/Middle School Director Reem Abu Rahmeh shared, “Anyone who has worked with Ryan recognizes that students are always his north star, and whether he is working with students or adults, he leads with curiosity and excitement that truly embodies the hope and joy of our mission!”

Lakeside is fortunate to have a deep bench: While Ryan serves as interim head through June 2027, he will share some of the Upper School director’s responsibilities with experienced fellow administrators. With strong and inspired leadership across the institution, we are confident that Lakeside students, families, faculty, and staff will be in good hands. 

Beginning the search for Lakeside’s next head of school 

With Ryan Boccuzzi stepping into the role of interim head of school, the Board of Trustees is able to turn its focus toward launching a comprehensive and inclusive search for a new head of school. The search will begin this spring, and we should have more information ready to share in March. 

Later this year, we’ll have opportunities to personally express our gratitude and appreciation for Kai’s many contributions to our community. In the meantime, if you’d like to send a message to Kai, you can send it to Lilli Forgette, who will pass it on to him. 

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. 

Thank you all for your continued partnership, care, and trust in Lakeside. 

With gratitude, 

Sean O’Donnell ’90, P ’25 ’27 

Board of Trustees, Chair

Lakeside School 

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