Lakeside School

Dear members of the Lakeside School community, 

Four months ago, Lakeside’s head of school search committee set out to find an inspiring and strategic leader, an educator committed to educational excellence, and a community builder who can connect with all Lakesiders. We wanted someone who would embody the joy of learning and the hope that our students and community bring to all of us. 

After a highly competitive search, the committee has unanimously recommended Lakeside's Interim Head of School/Upper School Director Ryan Boccuzzi to be our next head of school. Lakeside’s Board of Trustees, in turn, has unanimously accepted that recommendation and is proud to appoint Ryan Boccuzzi as Lakeside’s 12th Head of School, starting this summer.

A leader who knows and loves Lakeside

At the start of the search, many members of the Lakeside community asked, “Couldn’t we just hire Mr. Boccuzzi?” But the selection of a new head of school requires a deliberate and thorough process. The search was exceptionally competitive: educational leaders from around the globe were eager to take on the head role at Lakeside, leading an internationally recognized and respected institution. 

Over the past four months, the search committee reviewed over 100 candidates that educational search firm Carney, Sandoe & Associates selected for our review, interviewing 13 impressive semifinalists. In early June, the committee brought three finalists to campus for confidential meetings with representative groups of faculty, staff, administrators, students, and trustees. 

Through the search, Ryan Boccuzzi emerged as the top choice from a highly competitive pool of candidates. When our committee met in mid-June, we made the unanimous decision to recommend Ryan Boccuzzi as Lakeside’s next head. As fellow committee member Noah Bopp ’92 remarked, “There is no doubt in my mind that Ryan is one of the top head of school candidates — if not the top candidate — in the nation.”

As a stellar educational leader with deep ties to our community, Ryan represents continuity and momentum: He knows Lakeside’s culture, people, systems, strengths, and tensions and can lead adeptly from day one. We believe he is the right person to unite and inspire Lakeside at this critical moment. 

An inspiring and strategic leader 

As Lakeside’s assistant head of school/Upper School director — and Lakeside’s interim head of school since this winter — Ryan Boccuzzi has demonstrated his deep commitment to Lakeside’s mission, leading with courage and integrity, a steady sense of direction, and sound judgment. 

Committee members remarked on Ryan’s ability to set thoughtful and mission-aligned priorities, make informed decisions with clarity, and execute them in service of the school’s current needs and long-term goals. He is a bold and collaborative leader who can make hard decisions and then actively work to enact change, demonstrated in his leadership of capital projects like the Vassar Center, in moving the Upper School to an invisible device policy, and, most recently, in the launch of the Rooted & Rising initiative that reconfigures the Middle School into grades 6, 7, and 8 and grows the size of the Upper School. In a period of massive change, he has proved to be a decision-maker who remains calm and values-focused under pressure. 

Ryan received exceptionally positive feedback from the faculty, staff, and administrators who interviewed the finalists: 100% agreed or strongly agreed that Ryan has the professional qualifications, leadership style, and personal qualities to succeed as head of school. In particular, faculty and staff remarked on Ryan’s self-awareness about his identity, understanding of positionality, and the willingness to lead in the values-driven work of community, equity, and belonging. Carney Sandoe noted that this level of internal support is unprecedented in their many years of head searches. 

Committed to educational excellence 

As a seasoned school administrator committed to educational excellence in its broadest sense, the search committee believes Ryan will continue to lead Lakeside’s innovative approach to prepare students for the future.

Throughout his career, Ryan has led from a place of appreciation and understanding of faculty and teaching, and a focus on the academic, social-emotional, and developmental needs of students. His academic leadership spans multiple institutions: Before joining Lakeside as Upper School director, 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. Having worked as an administrator, teacher, dean, and coach, Ryan understands the complexity of modern independent schools. We feel confident in his ability to thoughtfully navigate, today and into the future, the intersection of educational excellence, student well-being, and a learning community rooted in shared values. 

Ryan is an educator, first and foremost. Through the search process, he demonstrated a sincere curiosity, growth mindset, and humility — modeling self-awareness, accountability, and actively seeking to learn from others — aspects of his approach and personality that were remarked on by his current and former colleagues. In a multi-faceted school such as Lakeside, he also brings a holistic institutional vision: Although his background is in teaching, Ryan values and understands how non-academic offices such as finance, communications, enrollment, facilities, and philanthropy, as well as the Board, interact as a system in an interconnected whole. 

A community builder 

Perhaps most importantly, Ryan understands that strong relationships build trust — the necessary foundation for all meaningful work. From his colleagues, we heard that Ryan has distinguished himself as a relational and empathetic leader. At Lakeside and beyond, Ryan excels at connecting with people, listening deeply, and making individuals feel valued and heard, even when delivering difficult decisions. Committee member and English teacher Avery Downing speaks for many of us when he shared, “Throughout the search process, Ryan stood out: His approach to innovation and problem solving was consistently and uniquely people and community first.” 

When students, teachers, and parents asked us if we could appoint Ryan, they were responding to a deliberate choice that Ryan makes to be present, engaged, and invested in every person at the school. Ryan views his physical presence on campus as a direct communication of the school’s priorities, and he understands the interconnected nature of our community, in which the sum is greater than the parts. At both the Upper School and Middle School, he has earned the respect and love of students and their families. 

Finally, Ryan brings a palpable sense of joy to this work. Anyone who has seen him cheering for kids at an Upper School house assembly or witnessed him cutting the ribbon alongside the Vassar family at the opening of our new building understands that he embodies the energy, engagement, and fun that we see every day in our kids. His joy and belief in this community will contribute to and deepen our connections to each other. 

To our community: Thank you

We are deeply grateful to the members of the head of school search committee for the commitment, insight, and care they brought to this competitive search process. Drawn from across the Lakeside community, the nine committee members encompass current and former trustees, current faculty and administration, alums, parents of students and alums, and education experts. The Lakeside search committee drew on all their knowledge of and love for Lakeside in representing the collective desires of the community, while our partners at educational search firm Carney, Sandoe & Associates — President Devereaux McClatchey, Vice President, Education Leadership Services Darryl Ford, and Senior Consultant Karen Whitaker — searched the world for the best and brightest in the field of education. 

Thank you to every person who provided input and advice during this search. In surveys and meetings, faculty and staff, students, parents and guardians, trustees, and alums shared their perspectives on what is distinctive about Lakeside and what we should look for in a new head. Your responses shaped the head of school position description, our rigorous process, an outstanding pool of finalists, and the culminating selection of Ryan Boccuzzi. 

Ryan will begin his tenure as head of school this summer. This fall, he will begin a national search for the next Upper School director, to begin in summer 2027. In the meantime, Ryan will continue as planned in the dual role while being supported by Upper School assistant directors Whitney Suttell and Jeff Bonar, Academic Dean Hans de Grys, and the now fully-staffed Upper School deans program. Additionally, Ryan will work closely with Associate Head of School/Chief Financial Officer Birage Tandon, Assistant Head of School/Middle School Director Reem Abu Rahmeh, and Assistant Head of School Jamie Asaka. Working together, the full team and all other directors at the school will ensure that Ryan has time to devote to his new role. 

We hope that you will celebrate with us this summer and next year as we formally welcome Ryan Boccuzzi to his new role as Lakeside’s 12th head of school. Please save the date of Thursday, Aug. 27, for a special all-community event marking this new era of Lakeside School! 

Thank you again for being part of this journey with us. 

On behalf of the Lakeside School Board of Trustees and head of school search committee, 

Melinda Lewison ’90 P’22 ’24 Head of School Search Committee Chair

Mark Klebanoff ’80 P’16, ’13, ’10  Incoming Chair of Lakeside School Board of Trustees

Sean O’Donnell ’90 P’25 ’27  Chair of Lakeside School Board of Trustees

 

Head of School Search Committee members

• Melinda Lewison ’90 P’22 ’24, committee chair
• Reem Abu Rahmeh
• Noah Bopp ’92
• Ai-Li Chiong-Martinson ’06
• Avery Downing 
• Mark Klebanoff ’80 P’16, ’13, ’10, incoming Board of Trustees chair 
• Michael Nachbar
• Latosha Smith P’27
• Brandon Vaughan ’06