Head of School

Head of School – Schechter School of Long Island

Join to apply for the Head of School role at Schechter School of Long Island.

Overview

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 and inspired by a spirit of inquiry, SSLI 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.

Position

• Develop and execute a strategic path forward that strengthens SSLI and positions it for long‑term success.
• Reverse enrollment decline and position SSLI as a destination for Jewish families across Long Island.
• Partner with lay leaders and donors to chart a facilities plan that matches the school’s ambitions and provides a home for future generations.
• Lead fundraising efforts, strengthening relationships with parents, alumni, and communal partners to secure the philanthropic support needed to realize the school’s vision.
• Act as a visible, approachable presence, knowing students by name, supporting teachers, and creating a culture of warmth, trust, and shared purpose.
• 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

The salary range starts at $318,000. The benefits package includes tuition assistance, medical, dental, and vision coverage, and a generous retirement plan.

Application Requirements

• 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 ( 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.