Eight Questions for Maria Kim, President and CEO of REDF

Maria Kim is the president and CEO of REDF, a venture philanthropic group that invests in employment social enterprises, which are businesses that provide jobs, training and support for those facing barriers to employment. REDF provides capital for growth and capacity building, and deepens learning and collaboration in the field.

Prior to joining REDF, Kim served as the CEO of Cara Collective, an organization that helps people who are experiencing homelessness and poverty attain jobs and opportunity. Cara Collective was a grantee of REDF during Kim’s time there. She’s also worked in the public sector, serving on the 2022 Entrepreneurship and Economic Mobility Task Force for the state of California and was a co-chair within Chicago Mayor Lori Lightfoot’s 2019 transition team. She’s also on the advisory boards of Procure Impact, First Women’s Bank, the Leadership Society Initiative and the University of Chicago Inclusive Economy Lab. 

We recently chatted with Kim about breaking down barriers to employment, her thoughts on the philanthropic sector, and making the move from grantee to leading the organization that once funded her work. Below are excerpts from that conversation, which have been edited for clarity and length. 

To start with, can you tell me a little bit about your background and how you came to be a grantee of REDF?

I used to work at an organization called Cara Collective out of Chicago. I was there for 16 years, the last seven of which were as CEO. REDF invests in social enterprises around the country, and [Cara Collective] was one of those social enterprises. At Cara Collective, we invest in a specific kind of social enterprise. So these are enterprises that exist to create jobs for folks who’ve been boxed out of the economy, folks coming out of incarceration, coming out of homelessness, etc. And that was our target population at Cara. So when I first met REDF, it was truly as a grantee, which is kind of cool, that it’s a full-circle story, now.

Can you tell me a little bit about your time at Cara Collective and the kind of work that you did there?

So this was a job training, placement and retention advancement organization for folks coming out of homelessness and poverty in Chicago. And then it expanded. The model in Chicago was also replicated two times, once in Indiana and once in Georgia. And the idea is that talent in so many people that have been boxed out of the economy already exists inside of them, but sometimes, life has knocked the esteem out of you, the confidence out of you, the everything out of you, and you need a community to not just remind yourself of the skills you already have, but then to refine and build new skills to increase your marketability for employment. 

So that’s what we did. And we talked about it in terms of not just attacking financial poverty but relational poverty. How do we reconnect people back into families, communities and their own kind of world? And we had two social enterprises. So these are businesses that compete in the market. But really, they exist to create jobs for folks who’ve been boxed out. Those two businesses were called Clean Slate and Cara Connects — kind of an exterior maintenance business and a staffing business. And REDF helped those two businesses to grow. So REDF’s intention is like, hey, let’s focus on this idea of a social enterprise because they often become kind of a dress rehearsal for folks to build skills, build confidence, build a resume, before getting higher-income-earning positions in the private sector and beyond. And so when they helped us to grow, we then created more jobs that created more mobility for the people that we serve. 

And so how did you come to lead REDF? What was that transition like, going from a grantee to leading the organization?

So REDF was at an inflection point, and my predecessor, Carla Javits, she’s shorter than me. So she’s five-something, but she is larger than life. She’s got a vision, a policy strategy, a way of seeing the world that is just on 10, on 11, even, and she was coming to retirement. And so they canvassed the field for successors. And I think that they had an eye toward, what would it be like if a practitioner were in that seat? What would it be like if somebody who we actually invested in was part of the leadership to kind of vision out those investments for the future? How would it make us more proximate to the work? And so I think that’s how I was able to be a part of the mix and ultimately secure the role.

What is it that brought you to this work? And how have your experiences influenced your work?

My career is kind of chunked out in big acts. My first act was actually in the private sector. I was in insurance for 15 years, and the second act was at Cara, another 15, 16 years. And the pivot point between the private sector and the purpose sector was actually 9/11. When 9/11 happened, I, like everybody in our country, and to some degree, in the world, we grieved in ways that, at least for me, in my lifetime, wasn’t familiar to me. 

That moment, I experienced two big shocks: the professional shock, as our organization was then quickly acquired by another company soon after 9/11, and a personal shock. If this is as precious as life is, if in one day, the whole world can change and turn upside-down, then am I really walking in my vocation? Am I really doing what I’m supposed to do? I was grappling with all that. Throw in a little bit of an early midlife crisis in there, and I realized, “Hey, I don’t think I am. I don’t think that I am walking in my vocation.” 

And so I spent a few years trying to figure that out and ultimately stumbled upon Cara and fell in love with this organization. While it has the tax status of nonprofit, one thing that I hate about the terminology that we use as a sector is, we identify ourselves by our tax status. And the truth of it is we are all kind of for-profit businesses. We just happen to reinvest our dividends in a different way. And when I came to Cara, I fell in love with the place because it was both rooted in business — how can we be financially sustainable and be vibrant in all ways? — and rooted in mission. How do we make sure that our North Star is completely anchored in people who have hit a rough go? How do we make sure that they, in turn, get their new beginnings? So that’s how I found my way to Cara, which ultimately made me find my way to REDF.

On that note, one of the big shifts we’ve seen in philanthropy is centering those with lived experience. Why is it so crucial to do so?

In our current strategic period at REDF, we’ve made it our intention to prioritize leaders of color and leaders with the lived experience of whom they employ. To zoom back out a bit, our primary customer is the entrepreneur, the person running the business that ultimately creates the jobs for folks who’ve been boxed out of the economy. In our current strategy, we want to say, of the entrepreneurs that we back, let’s prioritize leaders of color and leaders with lived experience. And the reason why it’s essential for us is because of an intuition that I think we all have — that people who are most proximate to the challenges are most creative about the solutions. People who are most proximate to the challenges feel deeply in their skin and their blood and their DNA, the why of those challenges and what can be done to upend them. And I think as a sector, as a society, for sure, and as a sector secondarily, we’ve not done such a great job of listening. We’ve not done such a great job of centering. And so part of our intent right now is to center and to listen. And then what we learned through that listening helps expand these opportunities for more people in the future.

And so pivoting just a little bit, what if anything, keeps you up at night, when it comes to philanthropy?

So right now, we’re at this point where everybody gets the fact that boxing people out of the economy is not good for anybody. It’s not good for them. It’s not good for business. It’s not good for society. And so we have this kind of groundswell of enthusiasm around upskilling and apprenticeship and getting folks into high-road careers, all of which I firmly believe in and I’m so supportive of. I think sometimes, what we miss in the thread is that people who’ve hit the toughest barriers to employment, it’s not so easy to step right onto that ladder and get up the apprenticeship chain.

And when I talk about this analogy, I want people to visualize it. We assume the ladder is on firm ground and we just grab the first rung and boom, boom, boom. The folks that our enterprises are serving are in a dinghy, hanging off a rope ladder in the water, lapping around, trying to get one rung of that ladder, and the waters are crashing back and forth. Finally, they get on the dinghy, only to find that you’ve got to make it from the dinghy all the way to the pier. You’ve got to make it to the pier. And what we as a sector and a society haven’t done is really look at what we need to fund below the surface. What do we need to make possible below the surface so that accessing that first rung to the high-road career is possible? And until we kind of zoom out and look at that total scaffolding of need, I feel like we’re going to end up perpetuating some of the very inequities that we’re trying to solve at this moment. So I guess, both from a philanthropy and from a kind of society perspective, I want desperately for us to solve that tension.

On the flip side, what about philanthropy excites you or gives you hope right now?

I think in a word, consciousness. The fact that everybody is more conscious, that folks are starting to understand, “It’s not just my macro actions I can do inside a big thing that I influence, but it’s the micro actions I take every day, the choices that I make.” The more that we do that, the more people will see themselves as philanthropists. It used to be this bougie title, but the more that we are conscious of our actions and our choices are rooted in a value system, the more we’re building a culture of philanthropy that is much more pervasive than it’s been in generations past. So if we get that right and we keep kind of riding that wave and supporting it, oh, the places you’ll go. I feel like the capital flows, the energy flows, all of that will just magnify because of this increased consciousness.

Any final thoughts?

Our sector can only do so much. The purpose sector can only go so far. The public sector is helping to fuel solutions that have traction and we’re grateful for that. And we need the private sector to lean fully in because the more that their organizations become radically inclusive, the more that they recognize talent for the skills that they bring, not the resume that they have, the faster our ability to get to that 10 million who are sidelined by the economy. The flywheel will just go infinitely faster. It takes all three sectors to come together with their whole back into it in order for us to really make a difference in our country.