
Waterside School
Head of School
Start Date: July 1, 2026
Coed Day School, Grades PK-5
148 students
770 Pacific St, Stamford, CT 06902
Educators Collaborative is pleased to support Waterside School in their search for a Head of School to begin July 1, 2026.
Mission
Waterside School is a co-educational PK-5th Grade independent school serving children and families regardless of limitations in income or circumstance. The School attracts and inspires students of academic promise and families deeply invested in their children’s success.
The School works to instill in its students a belief in their own worth, to cultivate in each a commitment to academic excellence, and to ensure the fullest development of every child’s character. Through a rigorous program of study and experience, the School empowers its students with the knowledge, skills and virtues required to enable them to excel as students, to gain access to superior academic opportunities, and to go forward to become the leaders of tomorrow.

Daily Pledge
“We promise to work hard, be kind and respect learning.”
A Distinctive PK-5 School
Founded in 2001, Waterside is an extraordinary place, unlike any other school serving the Fairfield County-area school market. Its $59 million endowment and annual giving that raises an average of $4 million a year provide financial resources to the school that are remarkable. Consistent with the school’s mission to serve children of promise and families of character regardless of limitations in income or circumstance, 100% of the students at Waterside receive financial aid, with 93% of the school’s operating funds coming from charitable donations and the endowment.
Waterside is located in a rapidly developing area of Stamford, Connecticut, a growing suburb of New York City bordered by the picturesque Long Island Sound. The majority of students reside in Stamford, and 90% of the students identify as Black/African American, Latinx/Hispanic, or multiracial. The school is housed in a gorgeous, thoughtfully designed building that opened in 2011. Graduates from Waterside go on to attend the top independent middle and upper schools in the area.
An Outstanding Leadership Opportunity
Waterside School seeks a visionary leader and passionate educator to step into the challenging role of Head of School. The school takes great pride in nurturing an environment that is compassionate and rigorous, joyful and disciplined, and intentionally develops head, heart, and spirit. An individual who brings experience, energy, integrity, vision, intellect, and an innovative spirit will thrive and find success in the Waterside School community.
You can learn more about this remarkable school and exciting leadership opportunity by reading our Information for Candidates, posted here.
How to Apply
Please reach out with any questions or to learn more about this opportunity. Candidates interested in this position are asked to submit the following materials by July 15.
- EC Summary Sheet and Disclosure Statement (Contact George Sanderson for these documents)
- Letter of Interest addressed to the Search Committee
- Current Resume
- Statement of Educational Leadership Philosophy
- Contact information for five or more professional references with name, relationship, phone number, and email address of each
George Sanderson, Partner, Educators Collaborative,
Listing Date: April 14, 2025

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