Mission, Vision, and Jewish Philanthropic Leadership: A Conversation with Rachel Garbow Monroe and Paula B. Pretlow
Claire E. Sufrin
Claire E. Sufrin is editor of Sources.
Rachel Garbow Monroe is President and CEO of The Harry and Jeannette Weinberg Foundation.
Paula B. Pretlow is Chair of the Board of The Harry and Jeannette Weinberg Foundation.
Credit: Kurt Hoffman
I reached out to the leaders of The Harry and Jeannette Weinberg Foundation to talk about best practices for philanthropic leaders, in their case a foundation with capacity to impact significant projects in the Jewish community and beyond. The Weinberg Foundation is headed by Chair of the Board Paula B. Pretlow, and President and CEO Rachel Garbow Monroe. Each of them is widely recognized for their leadership skills, and I specifically wanted to speak with them together so I could observe their give-and-take: how do two strong leaders work together across the lay-professional divide? I was also drawn to the Weinberg Foundation because it funds projects within the Jewish community and within the general community, and I wanted to know more about how it prioritizes needs. I learned quickly that it was founded with a specific mandate, and as our conversation progressed, I came to understand that Paula and Rachel’s work relies on their own vision of how best to best fulfill this mandate. You will learn more about their vision below; I was particularly struck by the breadth of its impact, from who they hire to staff the foundation to how they engage with their grantees to how they interact with leaders of other foundations.
Our conversation has been condensed and edited for clarity.
Claire: Paula, you joined the Board of Trustees of The Harry and Jeanette Weinberg Foundation in 2018 and have been Chair since July 2023. Rachel, you joined the foundation’s professional leadership in 2005 and became President and CEO in 2010. Could each of you please share what brought you to your respective role?
Paula: At every stage in my life, I’ve always given back. It’s part of who I am. And as time has gone on and my day job has ended, I’ve had more time to devote to nonprofit, foundation, and for-profit boards, including the boards of Northwestern University and the Kresge Foundation.
Northwestern gave me the opportunity for a world-class education, and it is an honor to help and give back to the university that opened doors for me. I knew about the Kresge Foundation from its work and buildings in educational spaces. In fact, I had many classes in the Kresge building at Northwestern.
I had not heard of the Harry and Jeanette Weinberg Foundation before I received a call from a headhunter in 2017. My rabbis hadn’t heard of it! But the foundation’s mission and leadership drew me to interview with the leadership and board, and then to say yes when they invited me to join. I’m so happy I said yes, because I was right: The mission aligns with my personal values, and the opportunity to work with the leadership, especially with Rachel, has been beyond my expectations.
I’ll add that my leadership and involvement with the Weinberg Foundation is informed by my service on other boards. Many principles and strategies commonly brought to bear in philanthropy can also be used in the corporate world and vice versa. I think of philanthropy as the heart combined with the head, and I think of conscious corporations as head combined with heart. I listen and hear different things in each space, and I try to bring principles and values from one side to the other. I think this makes me a better board member, which in turn, I hope, helps the organizations where I serve be more effective in their stated mission.
Rachel: I started my career in the corporate sector. In 1998, I serendipitously saw a job post in The Washington Post for a senior marketing position at The Associated: Jewish Federation of Baltimore. I worked there for seven years and was promoted to chief operating officer. I first encountered the Weinberg Foundation as a funder of The Associated. I went to a meeting with the Foundation one day in the winter of 2005 and was offered the position of Chief Operating Officer at the Foundation, which I held from 2005 to 2010 before becoming president and CEO of the organization.
Claire: Beyond the two of you, how is the leadership of the Weinberg Foundation structured?
Rachel: We've been through many different chapters in our leadership and in the evolution of the Foundation. We have a board of five independent, incredible, thoughtful partners. One is from Israel, and four are from across the United States. And today we have a staff of just over 70. Our assets total over $3 billion, and we distribute $150 million in grants each year, funding both the Jewish community and the community at large.
We do not follow a model where the board interacts with me alone—quite the opposite. The board knows our senior team, our grant team, our investment team, our administrative team. They know the organization and its staff well, and for me, that matters. We have a culture of excellence, but also a culture of connection and caring deeply about one another. Paula knows who’s getting married, who’s having babies, and even when someone’s having a hard moment.
Paula: Speaking of differences among organizations, the Weinberg Foundation is one where I feel that the staff is comfortable engaging with the board, with picking up the phone and calling me. I spoke on the phone today with a program officer in Hawaii who wanted to bring me up to date on meetings he had in San Francisco. It’s important to know about the work that is getting done in our communities so that we can fully represent what is happening in those places and help be a voice for the Foundation wherever we go.
Claire: The Weinberg Foundation is known primarily for its work in Baltimore, Hawaii, and Israel. I have to admit—it’s an unlikely combination. Why are these your geographical priorities?
Rachel: Our founder, Harry Weinberg, was an immigrant from Eastern Europe as a young child. He grew up in Baltimore, where he started his entrepreneurial efforts, and he is buried in Baltimore. Hawaii was a second home to Harry and his wife, Jeanette, through much of their adult life. Today, the Foundation’s assets include substantial legacy real estate, and the Foundation distributes over $15 million each year in grants to nonprofits in Hawaii that provide direct services to individuals experiencing poverty.
Harry Weinberg also lived and worked in Scranton, Pennsylvania, and in New York City. When he first traveled to Israel, he was quite moved to see the country and what it was struggling with and he began providing funding to several nonprofits, primarily serving older adults, across Israel.
These priority communities, as we call them, are the primary places where we focus our grantmaking, in addition to some national funding.
Claire: I'm struck by the way the foundation’s priorities are shaped by Harry Weinberg’s lived experiences. It’s clear that his philanthropy was shaped by his life and that it was dedicated to the places that he loved and the people who were there. It happens that there are emergency needs in the places where you are already working as you continue that work. But there are emergencies that happen in other places and need to be addressed, as well as non-emergency needs all over. Do you ever feel constrained by the directives Harry Weinberg gave when he established the foundation?
Rachel: Like most philanthropies, we have a very defined space, and we’re proud of it. We’re asked for more than 10 times what we fund each year, which tells us that philanthropy is not going to solve the largest problems in our community, in our country, in the world. But we can pick some specific areas and try to make a meaningful difference there. We ask our grantees to focus on what they’re best at and to do it really well, and we hold ourselves to the same standard. In addition to our geographic focus, we focus our grantmaking in five areas: housing, health, jobs, education, and aging. Some of these issues, like serving older adults, might not get as much attention, and we are proud to be among the top funders committed to making sure these important members of our communities are able to age with the dignity and support they deserve.
Paula: Harry made it clear that his assets should go toward addressing poverty. It's really important, as Rachel just said, to make the most impact in that huge bucket of needs. I think we’ve come to a point where, now more than ever, we are homing in on the specific ways we can make the most impact with our dollars, which are significant, but still only a drop in the bucket in terms of the vast needs that are out there.
Beyond that, through our learning and evaluation, we are now getting a better understanding of where and how we are making the impact that we say we intend to make.
Claire: How would you characterize the way you—the Foundation’s head professional and head lay leader—work together?
Rachel: Simple black-and-white issues are pretty straightforward, and we move through them with relative ease. The messy issues that we work through together are where it gets more complex, where multiple solutions are possible, and we need to determine what is best for the Foundation in the context of that issue at the moment. So, for me, it’s more about how we try to problem-solve the really messy stuff together.
Paula: I think we push and pull each other to try to bring out the best in our thinking. And we think differently. I’m not rubber stamping, and I do ask questions. Sometimes, Rachel will push back, and I will do the same. We share a leadership quality that allows us to do that and understand that we’re doing it because we care. We care about the people, we care about the mission, we care about the organization, we care about our grantees, and it’s all in service of that.
Rachel: I will often say to staff that we’re going to make whatever decision is best for the Foundation. It might not be best for me, it might not be best for person X who I’m talking to, but if we can agree it’s the right decision for the Foundation, we’ll both be behind it. As long as that’s our north star, and we are selfless in decision making, we’re good.
Claire: Paula, along the way, Rachel has described how she understands your job as chair of the board and how she experiences your work. I'm curious if you could describe Rachel’s job, what it is that she does.
Paula: Rachel is a leader who has a vision she articulates and is able to execute. She is an outstanding voice in our various communities—the Jewish and broader communities—explaining who we are and what our vision is. She does a great job of bringing board and staff all together to make decisions and carry out that vision. She brings vision, commitment, and passion.
Now, I do often have to say, “Rachel, slow down. It doesn't have to be done in the next hour. Not even in the next day.” Her mind is always working, and it is always in service to the Foundation. You have to run to keep up with Rachel, and I love that. She’s quick, with lots of ideas, and her leadership externally and internally are much to be admired.
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Claire: Rachel, how did you come to be this way?
Rachel: If our mission was not focused on helping people who are experiencing some of the hardest moments of life, maybe I wouldn’t have such a strong sense of urgency. We’re supporting housing for people who don’t have homes. We’re funding nonprofits with programs to enable older low-income adults to live out their lives at home instead of in an institutional care setting. For me, that matters. One thing Harry Weinberg said that I hold on to is, “While others are solving the ills of the world, someone will be hungry, someone will be sick, someone will be cold. That’s our job.”
Right now, there are crises in three of the places where we work most intensely and that makes our work especially important. In Hawaii, we are responding to the Lahaina wildfires and supporting the community’s long-term recovery.
In Israel, we are responding to October 7, and all that continues to happen there as a result, asking how we can support all the grantees and partners with whom we work. Finally, six months ago, the Francis Scott Key Bridge collapsed in Baltimore, and we anticipate it will take four years to rebuild. You can imagine the challenges of that.
This is our job. My husband likes to tease me and say if they ever do a documentary on me, they have to film how I make a peanut butter sandwich because I do even that like I’m in a hurry. I don’t know another speed. Paula's right to push me to slow down—I'm 55, and I'm figuring out how to take care of myself much better. But it’s taken a partner like Paula who has really encouraged me to do that.
Claire: Paula, when you were talking about Rachel a moment ago, you added the word “vision” to our conversation. Before, we’d been talking about the foundation’s mission, which was set by Harry Weinberg. What’s the relationship, then, between vision and mission?
Paula: Our mission was defined broadly by Harry. But Rachel’s vision really homes in on that mission so that it is focused and clear, so that everybody knows what it is and how we plan to get there and accomplish it. She has made the field stronger because her vision has inspired others.
Rachel: I also think it’s really important for a vision to address what the mission means in terms of how we behave as a foundation. I believe the grantees should be at the center of our work. I also believe that we must be humble, not in lip service, but genuinely, in our kishkes. This is not our money. It will never be our money. We must try to use it as effectively as possible. I also believe in the power of being kind to one another. This does not just mean being nice, it means being empathetic and listening and caring deeply and supporting one another as part of the work we’re doing.
We have a very strong commitment to diversity, equity, inclusion, and belonging, which Paula deserves enormous credit for. Thanks to her, we don’t just say DEI but DEIB to reflect our belief in the importance of creating a work environment and culture where all staff feel they belong.
On the investment side of the house, we set a goal of having 25 percent or more of our investment managers represent diverse communities. We’re currently at 34 percent. We have a staff that is also very diverse. Our staff is over 60 percent women, 50 percent people of color, 12 percent Jewish, and 5 percent LGBTQ. We might not look the way someone who thinks of us as a Jewish foundation might expect. But we need to be representative of the communities we serve, which include the Jewish community and the community at large.
Our commitment to caring about how we can make a difference in the work of DEIB is real. We ask: What percentage of our grants is going to groups led by diverse professionals serving diverse communities? We also think about our grantmaking with a gender lens. Roughly 2 percent of charitable giving in Israel went to women-led, women-serving organizations before the war. That number has not changed much, even with almost a billion dollars in emergency funding in response to October 7. We have to say that’s not right. Women should be represented as well as all people in our community.
If you have diversity of thought at the table, the results are better, whether it’s investments, whether it’s grantmaking, whether it’s how to put the train on the tracks, it doesn’t matter. Part of how we care about our mission is showing representation of community through these lenses.
Paula: Rachel, thank you so much for bringing that up because it really is part of our core. We not only talk the talk, we strive to walk the walk. As an example, when I joined the board in 2018, I asked our investment team: Where are the people who are managing the money and look like me? I suggested that we compare who’s managing our assets to the people we’re granting to and ask how we can do better at making that match. To Rachel’s and the investment team’s credit, we have done more, and with intention. We have not only achieved our goal; we have exceeded it.
We approach the work of DEIB with focus and intention. As part of our gender-focused lens in Israel, when we noticed after October 7 how little funding was going to women-led, women-focused organizations, Rachel and I, along with another one of our philanthropy partners, decided to take a group of women philanthropists to Israel and highlight this issue. The connections and relationships built, and the heightened awareness of the work that needs to be done, have been incredible. That is an example of Rachel’s leaning in with a sense of vision and mission.
Rachel: At this moment, when some may be questioning and even pushing away from DEI, our response has been to double down.
Claire: For lay people who are outside the process of grantmaking, who maybe have never applied for a grant or aren’t professional leaders in Jewish communal service, it can appear that the folks with money to give away are setting the priorities for the rest of the community. I know that this is a caricature, but there’s no question that philanthropists have power to determine which communal needs to address and how. The Weinberg Foundation receives 10 times more grant inquiries than you can fund. Your decisions have a real impact on what work can be done. How do you approach this responsibility? How is it tied to your sense of leadership?
Paula: Smart philanthropy has evolved and continues to evolve. Foundations including Weinberg have shifted to understand that, to do our best work, we need to learn from the people who are benefiting and have their voices at the table. Centering our grantees will make us better partners and collaborators in the communities in which we work.
Rachel: Sitting in your chair with your own experience, you may have ideas of what’s needed for children in an emergency domestic violence shelter in Baltimore or in a homeless shelter in Maui, but what you hear when you actually ask can be very different.
We spend time and money focused on listening to voices with real-world experience, which is the opposite of sitting in a boardroom making grant decisions. We talk to kids and teachers participating in educational programs, youth who’ve experienced homelessness. It’s not always easy, but it’s important.
We’re learning what matters to the community we’re trying to support, and we are trying to say to them that we are listening to them, and we are funding in response to what they are advising.
Here’s another example of why it matters that we listen to our grantees: If we fund a grant to support job placement for people who are really struggling to get jobs, and we expect to have a 90 percent placement success rate after two years, that nonprofit is going to feel it needs to pick the individuals who are easiest to employ among the community it serves in order to get that result. In a case like this, we’re creating selection bias in how we’re presenting the conditions for the grant. We need to understand from the grantees what they need to be effective. What will be a good measure of success that won’t undermine how they’re engaging, supporting, and welcoming individuals with significant barriers to employment?
At the same time, at the end of a grant period, we need to ask: How did you actually do? Tracking data and measuring progress are non-negotiable and another piece of the story that matters.
Claire: It’s become clear to me throughout this conversation that in addition to your efforts as leaders within the organization, you are striving for Weinberg to be a leader among philanthropic organizations.
Paula: This is very intentional. It is important that we signal our values to the rest of the world through how we operate. That is leadership, and it is who the Foundation is. And it’s important to us.
Rachel: Paula sits as the first Black Jewish woman in the role of chair at Weinberg in a very powerful way. And, please God, she won’t be the only, but she is the first. Those are some heavy bricks on her shoulders, and I want to make sure we as an organization are supporting her in all that she is leading.
Paula: I knew when I joined the Weinberg Foundation that we have a rotational chairship and that my time would come up. What a time this is for me to be sitting in this position, in this organization with everything in the world going on. I look at it as an awesome responsibility and opportunity. And I mean, “awesome” in its truest meaning of the word. Being any “first,” you carry the weight, and you carry the eyes looking at you, and you carry the burden. It’s a matter of living up to what is expected, not by others, but by me, and I have very high expectations for myself. So, I feel that burden in a good way. If I can be an example to the rest of the world about what is truly possible and achievable, then I’m fulfilling my purpose.
And this is fun! The work is important, but we also have fun.
Rachel: This work is hard to do. You have to breathe it, live it, care about it, and feel it. It’s part of you. For better and for worse. There are hard days. We all handle it differently. We’re regularly asking our grantees in Israel and on Maui, are you taking care of yourselves? What can we do to make sure you have the space to take care of yourself while you’re taking care of everyone else?
I’m very proud of the work we do. But I am prouder of the staff and the board behind this Foundation. I would put them up against any corporate or nonprofit or foundation entity in the United States.
I am grateful to be surrounded by extraordinary people who want to get things done and want to make a difference. The cup is half full, even if the water is not always clear. And for me, that is incredibly energizing and sustaining.
