Head of School (Chicago)

Chicago Jewish Day School is pleased to partner with DRG to conduct this search.

Read the full Opportunity Statement HERE.

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.

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.

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.