Head of School

Westchester Day School | Mamaroneck, NY, United States

Posted Date 11/30/2021

Westchester Day School, Head of School, Mamaroneck, NY

About the school:

Founded in 1948, Westchester Day School is one of the leading Modern Orthodox schools in the country. The co-educational dual-curriculum program for students in nursery- 8th grade is set on an idyllic campus located in suburban Westchester County, NY, just north of New York City. WDS is led by a team of innovative educators who partner with a parent body committed to academic excellence and developing kind and thoughtful young people. WDS is committed to customizing education to serve the individual needs of each child with the goal of instilling a love of learning.

WDS produces lifelong learners and mensches and inspires our students to work towards impacting the world around them. Our school engages with an academically rigorous curriculum that stresses Zionism and Torah values as it prepares our students to become active American citizens and leaders of the broader Jewish community. Our graduates are highly sought after by the top high schools in the tri-state area and are routinely identified as some of the highest achieving students at their respective schools.

For educators, the experience of spending the day on our lush 26-acre waterfront campus overlooking the Long Island Sound provides an unmatched environment to come to work and teach. For students, the campus serves as the backdrop for prime experiential learning that expands beyond the walls of the classroom, and is woven through the entire curriculum. Whether conducting a science lesson while wading into the Long Island Sound or teaching the laws of sheimot (burying holy books) as our students actually dig and cover buried books, our educators use our campus as a critical tool in what we believe is the most effective way to teach.

The WDS administration and faculty are at the forefront of defining the classroom of the future. Attention is paid to innovative practices, including areas where technology enhances the learning experience. The utilization of the iTalaam Hebrew language program in the preschool and early years of elementary school, Drone creation programs, and STEAM day are just a few examples of our programming. The school provides multiple professional development days for the entire faculty to have an ongoing opportunity to grow, learn and evolve. The faculty collaborates throughout the year to ensure our Judaic curriculum and Secular studies weave together to teach optimal skills and capabilities, opening minds and innovating across curriculums. Our classroom sizes are intentionally small to enable constant innovation and optimization of individualized student approaches.

Our leadership is committed to addressing the challenges of tuition affordability, and creating a sustainable model for high quality education. Since our founding in 1948, we have never turned away students based on financial need. WDS proudly offers four distinct and complementary programs to ensure that every family in the Westchester area can afford a WDS education (some, the first of their kind).

Our dedicated parent body partners with the school to support these goals and make WDS a central institution for the Westchester community; WDS has a thriving PTA, with class-based and cross-community events. When possible, hundreds of parents attend events on campus yearly.

For more information please visit our website www.westchesterday.org


A WDS student is a mensch. Our students conduct themselves with dignity and respect for themselves and others. They have a strong sense of right and wrong and are guided to be ethical in their lives.

WDS students become lifelong, independent learners who grow from inquiry, discovery, and reflective trial and error. They are problem-solvers who are flexible and adapt to new situations.

WDS students love God and find spirituality, fulfillment and joy in Jewish ritual, Torah-learning, and living a life of mitzvot. They understand that they are a link in a chain of tradition that has flourished for thousands of years, identifying and responding to the needs of others with sympathy and empathy. They proactively lead by example with a keen sense of justice and obligation.

WDS students appreciate and interact with the physical and intellectual world. They use their curiosity and pursuit of knowledge to develop a deep understanding of both secular and Jewish learning and the interplay between them.

WDS students are devoted to the State of Israel as key to the life of the Jewish people, and to Hebrew as our national spoken language and that of our foundational, sacred texts. They are also proud, grateful and contributing citizens of the United States of America.

WDS students exhibit humility and understand the unique value of every individual. They have confidence, understand their strengths and challenges, and take time to learn about and appreciate others. They work collaboratively to create, build and strengthen their community.

About the position:

We are seeking a dynamic and inspiring leader to play a key role in strengthening WDS’s position as the day school of choice for Modern Orthodox families in the greater Westchester area.


The Head of School will have a major role in student recruitment and retention.

The Head of School will be a strategic thinker and have the ability to plan and execute a clear vision.

The Head of School will be responsible for overseeing fundraising and development.

The Head of School will have administrative and fiscal oversight.

The Head of School will appreciate and support the important role social and emotional learning plays in the school.

We are looking for an individual with a track record of success in running and growing a Jewish institution. This is an important opportunity for an educator and/or an institutional leader to shape the future of Jewish education in Westchester County.

The Head of School will have a strong background in pedagogy and curricula strategy.


Qualifications for the position:

  • 5-10 years of experience in a senior administrative role in a Jewish communal institution
  • Experience either devising and implementing or being involved in a growth plan for a school and/or a major Jewish organization.
  • A skilled educator with comfort in both Judaic and General Studies, and an appreciation for technology.
  • A strategic thinker with a vision to develop, advocate and implement innovative strategies to advance the institution.
  • A talented communicator with strong interpersonal, written, verbal and presentation skills, and able to connect with parents, teachers and children. Has the skills to lead a strong, warm, and nurturing culture.
  • A successful fundraiser capable of building relationships with community leaders, alumni and other donors.
  • A passionate leader who personally embraces and exemplifies the school’s vision and philosophy.

Organizational Culture:

Faculty and staff work tirelessly to ensure that the practices and skills students develop during their time at WDS are inspired, joyful and creative. To succeed at that mission, the WDS culture is collaborative, with a constant focus on alignment of goals and sharing best-practices across grade levels. Led by an administration with a combined total of 35 years’ experience at WDS, the educational environment at WDS is fresh, exciting, renewed and future focused. The teachers and faculty work daily to promote a constant sense of appreciation for life and community, gratitude, and a creative and collective spirit around the halls of WDS.

About the Community:

The WDS Head of School will lead students coming from more than 15 communities across the New York area. Historically, children have commuted into WDS in Mamaroneck from 3 large thriving, growing and leading Orthodox neighborhoods - Scarsdale, New Rochelle and White Plains - but over the past 5 years or so, the neighboring towns in Westchester and Connecticut have seen enormous growth (thanks in a large part of COVID) that has brought in a new wave of eager, excited and curious families to tour, join, and consider WDS.

Communities are within easy distance to NYC for all that the city has to offer. Many established kosher restaurants are within a 15 minute drive from most surrounding neighborhoods to WDS, with many new more experimental cuisines popping up frequently, appealing to a vast array of palates.

All three primary feeder communities have experienced tremendous growth over the past few years - all three neighborhoods have seen upwards of 50+ families move in, over the past few years. White Plains is home to The Young Israel of White Plains and the Hebrew Institute of White Plains; Scarsdale supports one large shul, the Young Israel of Scarsdale; and New Rochelle supports a large Young Israel and Congregation Anshe Sholom (which is located in the heart of Downtown New Rochelle). Finally, families from other communities such as Riverdale, Stamford, Mamaroneck, Mount Vernon and Harrison attend their respective local shuls.


Parent Body:

Current WDS parents are at the top of their fields and aim to provide an academic experience to teach their kids the skills and capabilities that will enable them to be equally successful in a vast array of fields one day. Parents of WDS believe that their kids should experience leadership in the classroom, grow the skills to look at the world around them and identify ways to make it better for mankind.

Most WDS households are strongly engaged in supporting local charities, political organizations and/or candidates and Israel-focused non-profits. Parents want their children to be activists and respectful to those in need. WDS offers many family-oriented experiences to bring families to the beautiful WDS campus and contribute to important and timely causes.

People are diverse in their political affiliations, religious practice, and financial abilities and treasure that the parent body is diverse. Parents of WDS appreciate and aspire to provide a leading well-rounded academic experience for their children that focuses on STEM, Judaics, Israel, and Social-Emotional Learning, in addition to English Language and the Arts.

To apply to become the next Head of School at Westchester Day School send a resume and cover letter to Amy Wasser, Senior Director of School Services, Prizmah Center for Jewish Day Schools [email protected]

Full Time
Principal / Head of School
Organization Type
Education & Schools
Job Location

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