Cheryl is the director of the Day School Leadership Training institute, where she is both an alumna and served as a mentor for cohorts 9-12. She spent 21 years building and strengthening Saul Mirowitz Jewish Community School in St. Louis, Missouri, where she taught for 7 years and served as head of school for 14 years. Cheryl is a recipient of the Fred A. Goldstein Professional Leadership Award, the JPRO Visionary Award, Grinspoon-Steinhardt Award for Excellence in Jewish Education and the Stuart I. Raskas Outstanding Day School Teacher Award. She studied for her B.A. in Jewish and Near Eastern Studies and Education at Washington University in St. Louis. She holds a Masters in Jewish Education and received an honorary doctorate from Hebrew Union College-Jewish Institute of Religion. She and her husband Jon are the parents of two spectacular day school graduates, Ari and Gabe, and welcomed daughter-in law Emily to the family in 2022.

Ilisa believes that inspired, informed, and supported Jewish day school leaders are the key to healthy schools. As the Senior Vice President, Engagement at Prizmah, Ilisa works to help sustain and advance Jewish day school leadership through coaching and through serving as the director of YOU Lead, Prizmah’s signature leadership development program. Ilisa is a former head of school, an alumna of Cohort 4 of DSLTI (Day School Leadership Training Institute), and a sought after leadership coach with over 18 years of experience in Jewish education. She is a graduate of Barnard College of Columbia University and holds a master’s in Jewish education from the Jewish Theological Seminary. Ilisa earned her certificate of nonprofit board consulting from BoardSource and consults regularly with schools on governance. She is certified in The Leadership Circle Profile™ and earned a certificate in leadership coaching from Georgetown University. Ilisa is also an Associate Certified Coach (ACC) and member of the International Coaching Federation (ICF). Ilisa is deeply committed to developing strong lay-head partnerships and creating conditions in schools where leaders can thrive.

Partnerships for New Head Success

The first year of the Jewish day school headship is a challenging and pivotal moment in a leader’s career, and supporting new heads of school as they transition into new schools and communities is essential for the field. This year, Prizmah and the Day School Leadership Training Institute (DSLTI) partnered to forge The New Heads Initiative with the goal of doing just that. 

This particular collaboration is natural—both Prizmah and DSLTI are committed to supporting heads of school in all stages of their careers—and part of a larger history of partnership. Prizmah offers multifaceted support to heads, including weekly head of school meet-ups, leadership coaching for heads and their board chairs, and regular professional development opportunities. DSLTI is an intensive two-year, cohort-based fellowship for new and aspiring heads that many alumni have called the most powerful professional development experience of their career. 

Together through The New Heads Initiative, Prizmah and DSLTI provide a virtual network for support, professional development and connection for heads starting their first headship in 2022. 

For the roughly two dozen leaders who assume new headships in North American Jewish day schools each year, the challenges associated with transitioning into a new headship are immense and varied, and in need of attention and support. We envision an approach to supporting new heads that will help them feel well prepared for the particular challenges of their role, connected to colleagues and content experts, supported by a network of peers, and warmly welcomed into the Jewish day school field. The ultimate goal of the program is to retain talented heads of schools in the field in order to lead to healthier, more sustainable school communities. 

We believe that intentional practices focused on the transition of a new head of school will lead to benefits for the school and community and the field writ large, inclusive of greater stability, strengthening of the talent pool and creating space for schools to engage in long-term planning.

Through this program, and with additional support and attention focused on this critical juncture for heads, we hope to support the successful onboarding of new heads of schools into their positions and identify structures and systems that lead to longer head tenure. We also aim to cultivate conditions in which heads of school and board chairs can experience deeper alignment with one another: strengthened communication, clarity around goal setting, and collaborative systems for feedback and evaluation.

If we are successful, we will hear heads of school report they are feeling nourished and strengthened in their roles. In addition, we will see higher levels of sustainability, which might include: fewer reports of loneliness or isolation, a greater sense of efficacy and access to support, and stronger retention in the field. Through our partnership with one another in service of strong leadership for our schools, we hope that leaders will experience a greater sense of connection to the Jewish day school field, and to peers and leading experts who can assist them in achieving their goals.
During each virtual session, heads will have an opportunity to connect with one another around dilemmas of practice and engage in professional development. The staff is committed to connecting participants with experts in the field and experienced heads who can be helpful to them on this remarkable journey.
As heads of school, we become stronger by engaging with one another. And as organizations, Prizmah and DSLTI are stronger when we work together.

Ilisa Cappell from Prizmah and Cheryl Maayan from DSLTI are co-facilitating the sessions. The partnership and planning for these cohorts also includes Gavi Elkind of Prizmah, and Jane Taubenfeld Cohen and Ray Levi from DSLTI. 

For more information about Prizmah programs and opportunities for leadership development, reach out to Ilisa Cappell at [email protected]. To learn more about DSLTI, and to find out more about applications for Cohort 13 launching in the spring of 2023, reach out to Cheryl Maayan at [email protected].