Jewish day schools across North America are facing a leadership challenge: how to attract and retain the next generation of heads, principals, and administrators. A new report highlights that many schools struggle to fill senior roles, raising concerns about long-term stability and growth in Jewish education.

The profession often demands long hours, complex responsibilities, and skills that span both pedagogy and management. Yet, despite the challenges, Jewish day school leadership remains a deeply rewarding career—one that shapes communities, strengthens Jewish identity, and impacts thousands of students and families each year.

Experts suggest that solving the leadership gap requires rethinking traditional approaches. Schools and federations are exploring ways to make the profession more appealing by offering mentorship opportunities, professional development, and competitive compensation. Some also emphasize the importance of cultivating leaders from within—encouraging outstanding teachers and mid-level administrators to pursue leadership roles with the right training and support.

The discussion also points to a need for broader cultural change: shifting perceptions so that Jewish day school leadership is seen not only as a demanding role but also as a prestigious and meaningful career path. By investing in future leaders now, the Jewish community can ensure its schools remain vibrant, sustainable, and innovative for generations to come.

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Source: Jewish Telegraphic Agency, September 2025