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.

email George

Information for Candidates:

To learn more about this leadership opportunity, click here!

Letter to the Waterside Community

Dear Parents and Guardians,

We are excited to welcome finalists for the Head of School position to Waterside this month, and
a group representing the Waterside parent community will meet with each of the candidates.
Since launching the search last April, a large number of talented educators from around the
country applied for the position; of this deep pool, the search committee reviewed 15 especially
strong leaders and subsequently selected seven applicants to be part of a pool of semi-finalists.
The Search Committee interviewed each of these candidates and chose three finalists to visit
campus for a day and a half of interviews with faculty, students, the parent group, administrators,
and trustees.

Finalist visits begin on Monday, September 15th and will continue through the following week.
Brief biographies of the candidates will be shared with the community prior to each campus visit.
We look forward to receiving feedback on the finalists from the parent group, which will be
considered along with the feedback from faculty, students, administrators, and trustees. The
Board of Trustees hopes to appoint the next Head of School in early October.
We appreciate your enthusiastic engagement in the search process and look forward to sharing
more information with you as the process progresses.

Sincerely,

Lisa Stuart
Chair – Head of School Search Committee

Letter to the Waterside Community June 2025

Letter to the Waterside Community May 2025

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