Introduction   

Schechter School of Long Island (SSLI) is a vibrant, nurturing, and academically rigorous Jewish day school serving students from Kindergarten through 12th grade. Rooted in Jewish values, guided by the wisdom of tradition, and inspired by a spirit of inquiry, Schechter empowers students to grow as compassionate, knowledgeable, and engaged members of the Jewish community and the wider world. 

For more than 50 years, SSLI has been a cornerstone of the Long Island Jewish community, educating generations of students who go on to excel in their academic pursuits and serve as leaders in Jewish life and beyond. Parents, students, faculty, and alumni describe SSLI as warm, welcoming, and joyful — a place where students are known, cared for, and challenged to reach their highest potential. 

The school now seeks a dynamic, strategic, and inspirational Head of School to begin in July 2026. This is an extraordinary opportunity for a transformational leader to build on SSLI’s proud history and strong sense of community, and to imagine and guide its next chapter of growth. With a devoted faculty, passionate families, and engaged lay leaders, the next Head of School will have the chance to inspire confidence, strengthen Jewish life on Long Island, and position SSLI as a thriving, innovative center of learning and community for years to come. 

Mission  

SSLI is a Jewish day school whose dual curriculum of excellence educates and empowers its students to be critical thinkers, ethical leaders, and globally engaged citizens, striving to achieve their full potential and ensuring a vibrant Jewish future.  

Values 

SSLI’s core values serve as the essence of students’ identities and guide them through every stage of life.  

• Torah: SSLI instills a love of lifelong learning where questions are as valued as answers.  
• Ahavat Yisrael: SSLI fosters a love and commitment to the State, language, and People of Israel as central to Jewish identity and continuity.  
• Kehillah: SSLI celebrates the individuality and diversity within the SSLI family, and fosters an inclusive and caring community.  
• Mitzvot: SSLI sanctifies Hashem’s presence through the observance of Jewish practice.  
• Tefillah: SSLI encourages all students to find their unique voices in prayer.  
• Gemilut Chasadim: SSLI engages students in thoughtful acts of loving kindness, generosity and world repair- Tikun Olam.  

Facts and Figures 

• Founded: 1967 
• Enrollment: 219 
• Elementary School (Kindergarten-5th): 99 
• Middle School (6th -8th): 44 
• High School (9th-12th): 76 
• Employees: 68 
• Operating Budget: $8.8M 
• Annual Fundraising: $800,000 
• Accreditation: New York State Association of Independent Schools  (NYSAIS).  
• On the Web:  www.schechterli.org 
• On Instagram: www.instagram.com/schechterli 

The Program 

Schechter School of Long Island offers a dynamic dual curriculum that blends rigorous general studies with deep engagement in Jewish learning. Small class sizes and student-centered approaches ensure that every child is known and challenged, with project-based learning and individualized support at the core. 

Excellence in Learning 

SSLI provides a comprehensive program across the humanities, sciences, languages, and the arts, complemented by rich Judaic studies in Tanach, Mishnah, Jewish history, and thought. The school exceeds New York State standards and offers a wide range of Advanced Placement courses, including the distinguished AP Capstone track, preparing students to thrive at top colleges and universities. 

Jewish Life, Hebrew, and Israel 

Jewish values and Hebrew language are woven through every part of school life. SSLI’s Hebrew program helps students achieve fluency and confidence in reading, writing, and speaking, while connecting them deeply to Israel and the global Jewish community. Daily tefillah and weekly Kabbalat Shabbat build spiritual connection and a sense of belonging. The rhythm of the Jewish year is celebrated joyfully, from communal Seders that honor diverse traditions to song-filled Shabbat gatherings that unite students, faculty, and families. The school’s connection to Israel culminates in a three-week senior trip, where students immerse themselves in the land, people, and culture in transformative ways. 

Signature Experiences 

Innovative programs such as engineering, music and drama, experiential retreats, and cross-grade mentorship enrich the SSLI journey. These offerings develop creativity, leadership, and community, ensuring that students graduate with both strong academic foundations and a joyful, enduring Jewish identity. 

Position 

Schechter School of Long Island is at an exciting inflection point—ready for a leader who can build on its proud history and guide it toward a bold and vibrant future. This is a rare opportunity for a leader who can think expansively, bring people together around a shared sense of purpose, and turn that vision into meaningful, sustained growth. Working in close partnership with the Board of Trustees, the Head will help define and execute a strategic path forward that strengthens the school and positions it for long-term success. 

Central to that work will be reversing enrollment decline and positioning SSLI as a destination for Jewish families across Long Island. The next Head of School will bring fresh ideas, creativity, and a compelling story that inspires confidence and attracts new students. Hand in hand with this will be the need to address the school’s physical plant. The Head will partner with lay leaders and donors to chart a plan for facilities that can match the school’s ambitions and provide a home for future generations. 

Fundraising will be an essential part of this role. As a visible and trusted presence in the wider Jewish and Long Island communities, the Head will strengthen relationships with parents, alumni, and communal partners, and cultivate the philanthropic support needed to realize the school’s vision.  

Day to day, the Head of School will be a visible and approachable presence, someone who knows students by name, supports teachers, and creates a culture of warmth, trust, and shared purpose. In doing so, they will sustain SSLI’s proud tradition of academic excellence and joyful Jewish learning while building momentum toward an ambitious and thriving future. 

Qualifications  

• Visionary and strategic leader with a proven record of driving organizational growth and innovation. 
• Proven track record as an organizational leader and/or educational administrator. 
• Excellent communication skills, in writing and public speaking before groups of different sizes and constituencies.  
• Financial acumen: able to oversee budgets and set financial priorities.  
• Ability and willingness to participate actively and effectively in fundraising. 
• Demonstrated ability to hire effectively and build a cohesive, high-performing leadership team. 
• Proven success in change management and in building consensus among diverse stakeholders around a shared vision. 
• Principled leader who models integrity, strength of character, and high ethical standards. 
• Confident and decisive leader who empowers and delegates appropriately to skilled faculty and administrators. 
• Dynamic relationship builder who displays a sincere interest in each student, teacher, donor, parent, and community member, and engages others in the values and ethos of the school. 
• Visible, engaged, and enthusiastic participant in school life and in the broader Long Island Jewish community. 
• Deep love and passion for Israel, Jewish learning, and Jewish education. 
• Deep alignment with the mission and core values of SSLI. 

Benefits and Compensation 

Schechter School of Long Island offers a competitive and comprehensive compensation package for this role. The salary range starts at $318,000. The benefits package includes tuition assistance, medical, dental, and vision coverage, as well as a generous retirement plan.  

Application Requirements  

DRG is conducting this search on behalf of Schechter School of Long Island. Interested candidates should submit, as soon as possible, materials including the following: 

• A cover letter indicating why they are particularly interested in and qualified for the position 
• A current resume 
• A statement of leadership philosophy 

Application materials should be uploaded directly on the DRG website (www.drgtalent.com) by visiting the Schechter School of Long Island listing. 

Application Status: Accepting Applications               

Start date: July 2026 

This position description is based upon material provided by Schechter School of Long Island, an equal-opportunity employer.  

Tani Weissman, Partner,  tweissman@drgtalent.com  

Merav Schwartz, Associate Talent Consultant, mschwartz@drgtalent.com