Head of School Search

The purpose of this webpage is to provide the Waterside School community with ongoing information about the Head of School search process as it unfolds. Please refer back to this space for updates, and feel free to reach out to our search consultant, George Sanderson at Educators Collaborative, with any questions.

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Information for Candidates:

To learn more about this leadership opportunity, click here!

Letter to the Waterside Community

Dear Waterside Community,

I am pleased to provide an update on our plans to identify Waterside’s next leader, who will assume the role in July 2026.

As we approach Waterside’s 25th anniversary during the 2025–2026 school year, we are preparing to appoint a Head of School with the full authority and scope of responsibilities associated with the nation’s finest independent school leaders. In the past, we operated under a dual Executive Director/Head of School model. After careful consideration, we believe Waterside’s future will be best served by consolidating these roles into one position. This decision is grounded in the strength of our seasoned and highly respected team of academic and administrative leaders, whose expertise will be a vital asset in attracting top-tier candidates.

To guide this important search, we have engaged George Sanderson of Educators Collaborative. George brings extensive experience, having held numerous leadership positions at independent schools, most recently as Head of School at Doane Academy in New Jersey. Four trustees will collaborate closely with George throughout the search process: Mark Davis, Waterside’s Senior Advisor and former Head of St. Luke’s School for 20 years; Mike Schwabe, our Treasurer and incoming Board Chair; Daniel Taylor, co-leader of our Alumni Careers Initiative; and myself.

This spring, George will visit Waterside to conduct interviews and host listening sessions with representatives from across our school community. In addition, we will distribute a survey to gather your perspectives. Your thoughtful feedback will help us shape a leadership profile that reflects Waterside’s unique character and needs. Following this, the Head of School opportunity will be posted on leading education platforms, and George will leverage his firm’s network of over 3,500 educational leaders to identify exceptional candidates. The Search Committee will interview top candidates over the summer, and finalists will visit our campus in the fall.

Waterside’s Board of Trustees is fully committed to conducting a thorough, inclusive, and professional search. We are deeply grateful for your support and will continue to keep you informed as the process unfolds. If you have any questions during the search process, please reach out to Search@watersideschool.org.

Warm regards,
Lisa G. Stuart
Chair, Board of Trustees

Head of School Search Committee Bios

Mark Davis - Mark has served in many leadership positions in his independent school career including Head of School at St. Luke’s School for 20 years. At St. Luke’s, Mark led vision and strategic planning processes, significantly increased enrollment, launched a transformational leadership center, and stewarded technology to enhance student learning. Prior to St. Luke’s, Mark served as Director of College Counseling at Phillips Exeter Academy and The Taft School, which also included a 14-year teaching career in classical and American history, government, and art.
Since 2022, Mark has been a Senior Consultant and an Executive Coach for Carney Sandoe. Mark has been a leader in numerous professional and independent school associations, including chairing NEASC committees, serving as a trustee of NAIS, CAIS, REACH Prep, and Long Ridge School. Mark joined the Waterside board in 2024 and is currently the Senior Advisor to Waterside. Mark graduated from Yale University (Cum Laude), before earning a master’s in arts and liberal studies from Wesleyan.

Michael Schwabe - Mike has been a trustee of the Waterside School since 2011 and is currently the chair of the finance committee. Michael was the co-founder and portfolio manager of Artha Capital, an emerging markets hedge fund, from 2002 until 2020. He currently runs a family office focusing on public market and early-stage investments, and he writes a newsletter. Michael will be Waterside’s next board chair in July 2025.

Lisa G. Stuart – Lisa joined the Waterside board in 2016 and became board chair in 2020. Lisa has previously served on the boards of the Boys & Girls Club of Greenwich, chairing the board for four years; Greenwich Country Day School; Planned Parenthood of CT; and currently serves on the national board of CASA serving children in foster care; and the global board of Grassroots Soccer fighting AIDS in sub-Saharan Africa. She was an elected member of the Greenwich Representative Town Meeting for four years. A 1982 graduate of UC Berkeley, Lisa has a master’s in social work and in public administration from Columbia University.

Daniel Taylor - Daniel is the Co-Founder and CEO of Bags, a financial growth platform that helps small businesses manage their finances and borrow better money for business growth. With Bags, businesses make better growth decisions with their financial data and increase their access to equitable loans through an AI-powered monthly subscription. Our mission is to empower business owners to generate wealth, provide good jobs, and strengthen their communities.

Before Bags, Daniel co-founded AskTipster, a social data startup acquired by Tim Armstrong’s Flowcode in 2019. Daniel is a Stanford StartX alumni, former professional soccer player, and Brown University graduate. Daniel sits on the Board of the Technology and Innovation Council of the Guggenheim Museum, the #10 board of the U.S. Soccer Foundation, and the Board of the Waterside School.

Frequently Asked Questions

Have questions? Our Frequently Asked Questions document provides key information about the Head of School search process. If you don’t see your question answered, we encourage you to reach out at search@watersideschool.org – we’re happy to help!

Frequently Asked Questions