Head of School
Chicago Jewish Day School
Chicago, IL
Introduction
Founded in 2003, Chicago Jewish Day School was created to provide an outstanding Jewish and secular education within a multi-denominational community that welcomes families from across the Jewish spectrum.
Over the past 23 years, CJDS has grown from a small startup school into a thriving Junior Kindergarten through Grade 8 day school serving more than 250 students. During that time, the school has developed a strong reputation for academic excellence, meaningful Jewish learning, and a famously warm and supportive community. CJDS has attracted a talented faculty and leadership team, built a beautiful campus, established a strong culture of philanthropy, and become an esteemed member of the Greater Chicago Jewish community.
A defining feature of CJDS has always been its commitment to bringing together families with diverse Jewish backgrounds and practices. The school serves Orthodox, Conservative, Reform, secular, and unaffiliated families within a shared educational environment rooted in Jewish learning, Hebrew, Jewish values, Israel, and Jewish peoplehood. This commitment to multi-denominationalism remains central to the school's identity and is among the qualities most valued by members of the community.
CJDS is equally committed to academic excellence. Through a rigorous and engaging educational program, the school prepares students for noted success in high school and beyond while fostering intellectual curiosity, confidence, and a love of learning.
Perhaps most importantly, CJDS has cultivated a culture that is deeply relational and community-oriented. Students are known as individuals. Families develop meaningful connections with one another. Faculty and staff work collaboratively and are deeply invested in the success of their students and colleagues. This sense of warmth and belonging has become one of the school's defining characteristics and is frequently cited as one of the reasons families choose—and remain at—CJDS.
Today, the school enters an exciting new chapter. Following more than two decades of exceptional leadership and institutional growth, CJDS is well-positioned for continued impact. Enrollment is growing, philanthropic support remains strong, and the school is investing in the people, programs, and initiatives that will shape its future. With a talented faculty and staff, an engaged Board of Directors, a deeply committed parent community, and a growing alumni network that remains closely connected to the school, CJDS is poised for its next phase of growth. For the next Head of School, this is a rare opportunity to build upon an extraordinary foundation and lead one of Chicago's premier Jewish educational institutions into its next chapter.
CJDS at a Glance
Mission
Chicago Jewish Day School creates for its students a standard of excellence in both Judaic and General Studies. Our students develop a passion for learning and a strong sense of themselves as Jews and as human beings.
We inspire our students to:
· develop a strong Jewish identity through an integrated curriculum within a nurturing, stimulating, and creative environment
· become a community of lifelong learners
· respect and appreciate diversity
· love Torah, Israel, Hebrew language, and prayer
· be contributing, caring, and knowledgeable members of our community, our country, and the world
Facts and Figures
Founded: 2003
Enrollment: 254
§ Lower School (JK -5th): 187
§ Middle School (6th-8th): 67
Employees: 70
Operating Budget: $9M
Annual Fundraising: $3.5M
Accreditation: Independent Schools Association of the Central States (ISACS).
On the Web: chicagojewishdayschool.org
On Instagram:
instagram.com/chicagojewishdayschool
A CJDS Education
A CJDS education combines academic excellence, Jewish learning, character development, and experiential education in a warm and supportive environment. The educational experience is enriched by robust programs in the arts, music, technology, physical education, and other specialty areas, providing students with opportunities to explore their interests and talents. Students are challenged intellectually, encouraged to explore their interests, and inspired to become curious, confident, and engaged learners.
Lower School
The Lower School provides students with a strong academic, social, and emotional foundation during the most formative years of development. Through CJDS's innovative dual curriculum, students develop essential skills in literacy, mathematics, science, social studies, and Hebrew/Judaic Studies while cultivating confidence, independence, and a genuine love of learning. Social skills are intertwined with cognitive growth and intellectual progress. Guided by the principles of Responsive Classroom, CJDS’s approach to teaching fosters safe, challenging, and joyful learning environments.
Learning is intentionally hands-on, integrated, and inquiry-driven. Students are encouraged to explore their interests, ask meaningful questions, and engage deeply with the world around them. Through thematic studies, scientific investigations, design challenges, and other experiential learning opportunities, they develop the curiosity, creativity, and sense of wonder that serve as the foundation for future learning. Teachers work closely with students and families to ensure that each child is known, supported, and challenged.
Middle School
The Middle School experience is designed to prepare students for success in high school and beyond while helping them grow as learners, leaders, and community members. As students develop greater independence, they are challenged to think critically, engage with increasingly complex ideas, advocate for themselves and others, and assume greater responsibility for their learning.
Experiential learning remains a hallmark of the program. Students regularly extend their learning beyond the classroom through historical simulations, civic engagement opportunities, interdisciplinary projects, field experiences, and leadership experiences. Whether debating complex issues, exploring Chicago's cultural institutions, or applying classroom learning in authentic settings, students are encouraged to develop intellectual confidence, independence, and a deeper understanding of the world around them.
Jewish Life
Jewish life is woven into every aspect of the CJDS experience. The school's commitment to Jewish learning, Hebrew language, Jewish values, Israel, and Jewish peoplehood helps students develop a strong sense of identity, purpose, and connection to the broader Jewish community. Students engage deeply with Jewish texts, traditions, history, and values while developing an appreciation for the many ways Jews live and express their Judaism.
Jewish life extends well beyond the classroom. Kabbalat Shabbat, holiday celebrations, school-wide gatherings, family programming, and community traditions create a joyful and vibrant culture that shapes the rhythm of the school year.
A meaningful connection to Israel is a central component of the CJDS experience. Beginning in Junior Kindergarten, students engage with Israel through immersive and developmentally appropriate experiences that introduce them to the country's geography, culture, history, and diversity of its people. As students grow, that connection deepens through Hebrew language instruction, Jewish studies, current events, cultural exploration, and critical analysis of the complexities facing Israel.
The journey culminates in the school's annual 8th-grade trip to Israel, a transformative experience that allows students to experience firsthand the places, history, and people they have studied throughout their years at CJDS. Together, these experiences help students develop a lasting connection to Israel and an understanding of its central role in Jewish life and peoplehood.
Position
The next Head of School will assume leadership at a pivotal and exciting moment in Chicago Jewish Day School's history. Reporting to the Board of Directors, the Head of School serves as the chief educational, operational, and community leader of CJDS and is responsible for advancing the school's mission, building upon its distinctive culture, and ensuring its long-term success.
Working in partnership with the Board and a talented leadership team, the next Head of School will:
· Provide strategic leadership for all aspects of the institution, building upon the school's mission and vision while aligning the Board, leadership team, faculty, families, and broader community around a shared direction for the future.
· Serve as the steward of CJDS's culture and mission, preserving and strengthening the warm, welcoming, and deeply relational community that distinguishes the school while ensuring that its commitment to multi-denominational Jewish life remains vibrant and central to its identity.
· Ensure academic excellence across General Studies, Jewish Studies, Hebrew language learning, and Israel education, while continuing to strengthen curriculum, instructional practices, faculty development, and the structures necessary to support all learners.
· Lead the continued growth of the institution by building on enrollment momentum, strengthening admissions, marketing, enrollment, and retention efforts, and ensuring that the value and impact of a CJDS education are clearly understood throughout the Chicago Jewish community.
· Strengthen the school's long-term sustainability by partnering with the Board and advancement leadership to broaden philanthropic support, thoughtfully steward and transition key donor relationships, grow the endowment, and advance future campus priorities.
· Build upon the strength of the existing leadership team by empowering others, delegating effectively, and building the systems and leadership capacity necessary to support the school's continued growth.
The Ideal Candidate
The ideal candidate will be an inspiring and collaborative leader who embraces the mission of Jewish day school education and will build strong relationships across diverse stakeholder groups.
Successful candidates will demonstrate:
· A deep appreciation for and commitment to the mission of CJDS.
· Exceptional relationship-building and community leadership skills.
· Educational leadership experience and a demonstrated commitment to academic excellence.
· The ability to inspire trust, develop people, and build strong teams.
· The ability to balance confidence and decisiveness with humility, reflection, and a willingness to learn.
· Financial and budgetary fluency and an understanding of nonprofit and independent school operations.
· A proven ability to lead fundraising efforts and cultivate major donors.
· Strong communication skills and the ability to serve as a leading ambassador for CJDS.
· The ability to build leadership capacity by empowering others, delegating effectively, and bringing out the best in faculty, staff, and administrators.
Most importantly, the next Head of School will understand what makes CJDS special and possess the vision, warmth, and leadership necessary to guide the school confidently into its next chapter
Additional Core Competencies
The Head of School at CJDS will be able to demonstrate the following core competencies at the highest level.
Benefits and Compensation
The salary for this position aims to be competitive and commensurate with experience. The salary range for this role is $250,000-$300,000. CJDS offers a comprehensive and generous benefits package including medical, dental, vision, and retirement.
Application Requirements
DRG is conducting this search on behalf of Chicago Jewish Day School. 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 by visiting the Chicago Jewish Day School listing.
Application Status: Accepting Applications Start date: July 2027
This position description is based upon material provided by Chicago Jewish Day School, an equal-opportunity employer.
To apply for this position, please click HERE.
Dara Klarfeld, CEO, dklarfeld@drgtalent.com
Tani Weissman, Partner, tweissman@drgtalent.com
Shanna Jadwin, Talent Consultant, sjadwin@drgtalent.com