skip to main content
A Conversation with Alum Winnie Sandler Grinspoon

We recently spoke with Winnie Sandler Grinspoon, president of the Harold Grinspoon Foundation. She talked about everything from her time at Stroock to the work she does now. Winnie filled us in on the foundation’s projects, goals, impact worldwide and how the foundation stepped up during COVID to meet the needs of children and camps. She even shared what she loves about work and enjoys in her free time. In recognition of her work in leading the pioneering philanthropic work of the Grinspoon Foundation in the field of Jewish education, The Jerusalem Post recently named Winnie among the 50 Most Influential Jews of 2021.

Q: Tell me about your time at Stroock. What did you enjoy most about working at the firm?

Stroock was my first job out of law school, and I was there for about 6 years. I had a terrific experience at Stroock. I learned to be a litigator from some of the best in the business. I was given a lot of responsibility early on, and also some terrific opportunities. A highlight was presenting the opening statement at a trial in federal court as a mere third-year associate. I gained a lot professionally, but my favorite memories of Stroock are of the people I got to work with.

Q: After working in big law, what was going out on your own like?

WSG: It was a good change at a stage in life when I had young kids. I found a niche, handling employment and fair housing matters before administrative agencies. I could handle matters in different jurisdictions. I was able to work from home. 

Q: Tell me about the Harold Grinspoon Foundation and your role.

WSG: I’m the president of the foundation and I’m in my seventh year in that role. Harold Grinspoon is my father-in-law; he created the foundation 30 years ago and has asked me to lead it forward. We have a team of approximately 150 people. We support projects that enhance vibrant Jewish communities. We focus in certain targeted areas, including Jewish summer camps, and endowment building for Jewish organizations. Our best-known project is PJ Library, which distributes Jewish-themed children’s books and resources to hundreds of thousands of children on a monthly basis in 30+ countries to help share Jewish values, culture and traditions.

Q: What skills and lessons from law practice proved to be most helpful to you in your current role?

WSG: On any given day an issue may come up regarding a contract, an intellectual property matter, a grant agreement, an employment question or a tax matter. The foundation is a public charity and we raise funds, so we need to understand which gifts we can accept based on our legal status. It has been helpful to know how to spot issues that require outside expertise.

Q: Tell me about PJ Library. What do you enjoy most about that project?

WSG: It has been fascinating to help develop an idea into a large-scale, award-winning project that now has a global presence. We started PJ Library back in 2005 as a local program in Western Massachusetts sending books to 200 kids. Since then we’ve distributed 44 million books and counting to kids in more than 30 countries. We are creating a richer canon of children’s stories and content with Jewish themes through our own publishing imprint, our storytelling podcast, and interactive activities. I really enjoy working with the creative teams.

It is energizing to see the impact we are having. PJ Library is a feel-good project. We get thank you notes every single day from people who appreciate what we provide. For some, these books fit right into their family life, and for others, the books help to reconnect them to their Jewish heritage. We have a lot of interfaith families in the program, and often it is the non-Jewish spouse who is really interested in the materials we produce. People who didn’t have a Jewish childhood are eager for knowledge and the ability to pass on stories and traditions to their children. 

In normal times I travel a lot in my role, and it is fascinating to visit Jewish communities in different parts of the world that look different than ours. In places like Russia and Ukraine, for example, the families I meet are hungry for resources and content that connect them to a Jewish heritage they are reclaiming. In some countries, like Israel, children’s books are expensive, so free books are especially welcome. In some very small Jewish communities, PJ Library may be one of the few programs available for Jewish kids, such as in remote parts of Brazil or in Ireland or Dubai. We also provide books to kids in U.S. military families wherever they are stationed. It feels great knowing that we are helping parents and kids celebrate their Jewish identity in so many places around the world.

Q: How about the camp-focused project?

WSG: We provide free management consulting services to more than 100 Jewish summer camps across North America to help with strategic planning, fundraising and board development. We offer financial challenge grants to help camps raise funds and build endowments. Summer camp is such a transformative experience for so many kids, and we know the camps with effective boards, skilled professional leadership and ample financial resources will grow, innovate and offer the best camp experiences over the long term.

Q: I know about philanthropy generally, but how does public-private partnership philanthropy work and how does the foundation engage in it?

WSG: In Israel, we have a strong partnership with the Israel Ministry of Education to provide books to kids through the public school system. We operate two separate programs there. One is a Jewish-themed PJ Library sister program in Hebrew called Sifriyat Pijama (Pajama Library). We also run a separate secular, culturally appropriate literacy program for children in Arabic called Maktabat al Fanoos (Lantern Library). Working with the Ministry of Education, we are able to distribute hundreds of thousands of books each month to children across Israel through the school system. Teachers use the books for projects and activities in the classroom, and children then get to take the books home and keep them to build home libraries. We each benefit greatly from this partnership.

Q: What are the most challenging aspects of the work you do, especially now during COVID-19?

WSG: At the start of the pandemic, we faced supply chain issues like everyone else. For example, many publishers print their books in China, so when China shut down, that affected us. There was a paper shortage too. Prices increased. We had to change some of our business operations to make sure that we could deliver our products on time. For example, we bought books earlier and held more books in inventory. I’m happy to report we are doing a good job and have been able to deliver books each month to kids across North America. We haven’t missed a beat, but getting it done hasn’t been simple.

Our primary model is to deliver books directly to a family’s home each month through the mail. But as I mentioned, in Israel and in certain other countries we deliver books through schools, and that has been challenging as schools have had to open and then close repeatedly. When we'd hear that schools were opening, we’d quickly ship the books. When they closed again, we’d warehouse the books. We’ll see what this year brings.

Q: How about the camp program? Nearly all camps closed last summer.

WSG: True. Camps were shuttered. As the pandemic was taking hold in March 2020 we realized it could have dire consequences for the entire camp field. We also knew we were uniquely positioned to help with resources and expertise. We quickly offered a $10 million challenge grant to help the camps raise matching funds to get them through the very difficult year, and we did another $10 million challenge with another partner this year because the camps still have significant financial burdens. Our team helped the camps navigate the PPP loan program, the new health regulations, and other issues. We looked to see where we, as a foundation, could be most helpful in getting camps through this difficult time. Thankfully most camps were able to operate throughout summer 2021 and give kids a happy summer experience.

Q: How did the foundation weather the pandemic, keep donors engaged and donations coming in?

WSG: We continued to communicate with all the people who contribute to and support what we do. We kept them in the loop on how we were adapting, how we were stepping up, and where the opportunities and needs were. We changed our language in solicitation letters to reflect the changed circumstances. We were respectful of the fact that many people who had contributed in the past to support PJ Library would not be able to do so this year.

A lot of people saw how PJ Library was able to be a constant in uncertain times. People saw the value in the program, especially the enhanced value we were able to offer through the pandemic, and they contributed generously.

As for camps, we structured our challenge grant to incentivize others. We offered a dollar-for-dollar match for any tuition deposits that parents converted into gifts. Thousands of parents converted their deposits to gifts. We incentivized all other gifts with a 1:2 match. Our first $10 million challenge grant raised an additional $16 million from thousands of contributors. People knew it was a make-or-break moment and were really generous.

Q: What were some of the ways you reached children and helped parents during the pandemic?

WSG: We started running online activities for kids throughout the day. Families  stuck at home could go on the PJ Library Facebook page and watch a live story time, a virtual field trip, a sing-a-long, a craft along, or some other fun, child-centric activity. We generated and curated a lot of great online content and we set it up at regularly scheduled times, five times a day, so parents could plan around it. If parents had to get work done, they could rely on the schedule to find something from PJ Library to engage their kids.

Q: Do you have an in-house legal team and what qualities do you look for in outside counsel?

WSG: Our head of HR has a law degree and we have one lawyer in-house who does most of the contract and grant review and negotiation. In terms of working with outside counsel, we look for efficiency, responsiveness and cost sensitivity.

Q: Finally, what do you enjoy doing in your free time?

WSG: I like to be outside and be active. I enjoy skiing, hiking, running, and walking in the woods. I plant a fabulous vegetable garden each summer. I love the rare occasions when my husband and I get to spend time with our awesome adult kids. We’ve traveled extensively as a family, and I look forward to getting another trip on the calendar, hopefully soon.