Episode Notes

Learn more:

• Follow Leon Wilson and Sam Caplan

• Explore the Cleveland Foundation

Here are topics, people, and organizations referred to:

• Katie Niemann of Houston Endowment

• Technology Association of Grantmakers (TAG)

• Amara’s Law

• NTEN

• Social Innovation Summit (June 7-8, 2022)

Interested in more quality content about philanthropy tech? Here are a few Submittable resources:

• What Comes Next: How Tech Fits into Your Social Impact Strategy (Webinar)

• Moving Philanthropy Forward in 2022 (Guide)

• 9 Ways Data Science Can Accelerate Your Social Impact Work (Blog)

• The Review (Bi-monthly newsletter by Sam Caplan)

Transcript:

Welcome to Impact Audio, a podcast at the bustling intersection of philanthropy, social impact, and technology. I’m Rachel Mindell and it’s great to be with you. 

Today’s episode features Leon Wilson, Chief of Digital Innovation & Chief Information Officer at the Cleveland Foundation. Leon joins Submittable’s Sam Caplan for a conversation about breaking into philanthropy tech and leading with a strategic, community focus. 

Although you’ll hear Leon briefly discuss his background, I’d highly encourage you to check out his full bio on the webpage for this episode—Leon brings a wealth of unique expertise to his professional role and to conversations like this one. 

Thanks for being with us today and please enjoy.

SAM CAPLAN: Leon Wilson of the Cleveland Foundation, you were my special guest on Impact Audio. Welcome, thank you so much for joining me my friend. 

LEON WILSON: Thank you for having me. Looking forward to the conversation. 

SAM CAPLAN: Definitely. So Leon, what I thought we might do just to get started here is I would love to hear just a little bit about your journey, sort of like from your beginnings in Detroit to what led you to your current role in the Cleveland Foundation. 

LEON WILSON: Sure I'd be more than happy to. So as you mentioned, I'm a native from Detroit, Michigan. That's where I went to high school and that's where I fell in love with working with computers. Back in high school I was fortunate to go to a public high school where we had a computer lab and it was more of a prep high school. It's the same school that people like Diana Ross went to. If you're someone in Detroit, you went to my high school. 

[LAUGHING] 

But along with that I was an undergraduate and computer science at Michigan State University; stuck that out and from there moved on to corporate IT. I spent about 20 years in various corporations as in-house staff, IT managers, IT directors, roles of that nature in a lot of different industries. As well, I also spent some time in IT consulting for Fortune 500 companies and so forth. 

I had a very eclectic career whether it was the auto industry, the healthcare industry, the consumer goods industry, the banking industry, the real estate industry, to name a few. I'm always proud to say that some of the tools that people use today, like Zillow and Trulia, I was designing tools like those back in 1996 operating over a 24 baud modem. 

[LAUGHING] 

SAM CAPLAN: I had a 300 baud modem when I bought my very first Atari 400 with my bar mitzvah money back in the early 80s. 

LEON WILSON: Yeah, but nonetheless, while I was working in corporate IT and I was working at a Blue Cross Blue Shield back in Michigan at the time, I got a call from a recruiter wanting to go work for a nonprofit. And surprisingly when I first heard about a  job opportunity working for a nonprofit I joked and said you guys can't afford me. And I just pretty much discarded it, but then the recruiter was very persistent and reached back out to me. And I said, well, let me see the job description. 

And after looking at the job description, I have to tell you Sam, that the opportunity to kind of leverage all the skills and contributions that I did throughout my career and be able to center that and help work with nonprofits was very attractive. I was looking to make a different kind of shift anyway at that time in my career. So I did that. And that's what led me down the rabbit hole of working in nonprofits, nonprofit tech, and getting more familiar with philanthropies, major foundations, back in Michigan. So then when this opportunity presented itself here in Cleveland, Ohio working for the Cleveland Foundation, I jumped at the opportunity. And I haven't been underwhelmed with the opportunities I have working at the Cleveland Foundation. 

SAM CAPLAN: You said you were looking for something different. And I'm paraphrasing a little here, but it feels sort of a common thread with a lot of technologists who land in the nonprofit sector is that many of us reach a point in our career where we are looking for something different. What was that for you? What were you looking for that was different? 

LEON WILSON: Well for me, I was hitting a wall as far as succession and moving up the chain, the hierarchical chain, at my organization. So as I looked at this opportunity to be more entrepreneurial, and take more risk, and be given a lot more leeway and opportunity, I took advantage of making a lateral move instead of a vertical move. And from that, again yes, I gave up bonuses, annual bonuses, and stuff like that but the opportunities that it lended me put me in positions to really network with the right people to build my bench strength as far as strategic planning, strategic analysis, and understanding technology from a strategy standpoint. And helping organizations, small and mid-sized organizations, better understand how they can leverage technology to support their particular mission. 

SAM CAPLAN: Yeah perfect, so one thing Leon that I have always really loved about you is that you're a different kind of cat in the sense that… You are very attuned to innovation. And I would describe you as-- I would go so far as to say I think you're a pundit you think a lot about how technology may benefit us at some point years down the road. Do you feel like that's something that you brought with you from your corporate career or is that just like part of your DNA? How did-- what led you to being such an innovator? 

LEON WILSON: Well, I was always fascinated with whatever company I was working in developing a mastery for that industry. And with that mastery of the industry about how the industry works, then I was able to better understand the role that technology plays in that industry. So I was-- that's just something-- the way I always thought. And it helped me immensely as far as I navigated working on special projects and really being able to synthesize what the value proposition for certain systems, certain tools, certain devices, and things of that nature. 

Now when I took that skill set and went into the nonprofit sector where I had to be far more entrepreneurial than I ever had been, now I had to start thinking about strategy. Because at the time when I worked at a nonprofit I was running what would be called a managed service provider but for nonprofits. So I had to then market my service. I had to market my product. I had to be more strategic thinking about price points and things of that nature. And also because I'm now charged with helping nonprofits to leverage technology, I had to go deeper then, as you said, the basic blocking and tackling of infrastructures, emails, and things of that nature, and really start to listen to what are other organizations using that I wanted and bring that expertise and knowledge and leadership to those mid to small sized nonprofits so they can capitalize on that. 

SAM CAPLAN: Right and so speaking of those like nonprofits, so you work at the Cleveland Foundation. I think it's the oldest Community Foundation in the country. And I think one area where you and I differ a little bit is that while we both really enjoy thinking about cutting edge technology and innovation and sort of re-imagining how technology can reshape the social sector, I tend to sort of keep my head up in the clouds. You are a more boots on the ground working with these nonprofits. 

I think your perspective has been that nonprofits-- for many nonprofits they don't really care about machine learning, and artificial intelligence, and cryptocurrency. They're still struggling to get the basics right? 

LEON WILSON: No, you're absolutely right. But then you have to look at the dynamics of a nonprofit. Most people when they start a nonprofit or when they go to become executive director for a nonprofit, they're doing it because of a calling. They're doing it because they're mission driven. They're compelled to try to tackle some type of socially wicked problem or issue or something of that nature. And with that, that's where their focus is. 

They're not coming in from-- with a Harvard MBA and want to try to grow the ROI and grow the business from 1 million to $10 million in the next three years from that standpoint and trying to look at quarterly results from a financial perspective to cater to shareholders and stockholders' and things of that nature. They're driven to-- with their board, they're driven by how are they making an impact in the community that they're trying to serve. So they're very focused on that, almost to a fault, because then a lot of times that doesn't lend them time or mental capacity to think about how they ought to be investing in technology to help propel their work. 

SAM CAPLAN: Right, right. All right, so you have a dual role at the Cleveland Foundation. You are the chief of digital innovation and the chief information officer. So one thing that I think is just super fascinating about what you do is that in addition to being the CIO you also get to work with nonprofits in your community and make grants to help support the work of those nonprofits. Right? 

LEON WILSON: Yes I do. 

SAM CAPLAN: So tell me about that. How does one influence the other? So when you're spending your days-- when you have your CIO hat on at the Cleveland Foundation and you're thinking about your staff, and how you help center the grantee experience, and how you expedite grant making, and how you make it a great experience for all the individuals and Cleveland who donate to the foundation, and make grants through your organization how does that influence you thinking about technology when you are then interacting with the nonprofits who are trying to do this mission critical work? 

LEON WILSON: Well so to your point, as a CIO I'm looking at it from the user experience when I'm looking at the grantee for that standpoint. How are they interacting with our systems? How are we capturing data? How are we engaging with them through tools and technologies and so forth? How are our various staff members leveraging all those tools so they can accelerate the deployment of funds or to make smarter, better decisions about our funding or for our advancement team? Because we’re a Community Foundation, we are also doing fundraising. How are they using analytics? How are they using data to do prospecting for future donors and future benefactors and be partnering with their estate attorneys and people like that? 

Those skill sets just basically being a CIO helped shape how I now interact with nonprofits as a grantee when I'm a particular funder. Because now when they're coming to us for some form of a technology centric grant, I'm using my CIO experience to see are they asking all the right questions? Are they looking at all the right things? Do they truly capture the total cost of ownership for that particular software tool, that particular system? Are they engaging with the right client customer-- right contractors and consultants? How are they going to leverage-- how are they going to be able to maintain this after our funding goes away? 

So I take that CIO expertise as a technologist-- because they typically don't have a technologist on their staff. And 9 times out of 10 they don't have a technologist on their board. So they're at the mercy of some consultant that is telling them, here's what you need, here's what you need to do, here's how much it should costs you, and all that kind of stuff. As a CIO, I'm able to sniff through the sizzle and steak, and the fluff, and what's being inflated, what's being underinflated, and things of that nature to then help push back and challenge them to say, here are some other things you need to be factoring in. If you really want to address your social mission you need to be doing this, you need to be factoring this in. 

So I truly believe that being a CIO helps me to look at those particular technology centered grants more keenly. And I would say that for any CIO at any foundation who would have the opportunity to participate with their program officer and program directors. For the program officer and program directors that's the value proposition that CIO, that the VP of IT brings. They understand the nuances of that technology. What questions ought to be asked? What's being missed? What's being overlooked? So they can really help shape that grant proposal more finely. 

SAM CAPLAN: So there is an additional role for a CIO, for a grant maker, that goes beyond just managing the technology within the walls of their own foundation you're saying? Like in other words, we should be getting much more involved with the nonprofits and helping them think through the role of technology with their interventions. 

LEON WILSON: Absolutely, if their foundation would let them. If their foundation will allow them. If their foundation will endorse it and see the value in doing so. Then the CIO would then have the opportunity to provide that particular value adding up to that. Now that being said, as you mentioned earlier along about me, where I'm not just thinking about the nuts and bolts of the infrastructure, I'm engaged. I want to have those kind of conversations. I want to talk about technology from a strategic standpoint. 

So the everyday IT director has to want to be involved, then allow again their own mental capacity to think about that. You can't be so buried in the weeds focused on every single new virus definition and all that kind of stuff and have 19 different Microsoft credentials and certifications. You've got to have other certifications so that you can really look at these technologies from a strategic standpoint. 

SAM CAPLAN: Yeah. So let me switch gears a little bit here. Philanthropy and grant makers for the last couple of years have really been focused on this concept of equity in grant making. And you are a Black man serving as the CIO of one of the largest foundations in the country. Do you feel like you're beginning to see more people of color being given the opportunity, especially in the world of technology to take on more leadership at large foundations or nonprofits for that matter? 

LEON WILSON: While there is great diversity or I think at least growing diversity with more people of color in the grant making space, when you now layer that with technology grant making that's when it starts to get far more sketchy, more narrow. And then when you layer that on top of like say at a senior level then it gets even more sketchier. So yes, we're far and few between. I don't see many individuals, people of color in my position doing the work that I do. I may engage with others, you know your run of a mill program officer or a program director that might be doing this kind of work. But they're not at the senior level where they're able to influence the strategy and also a lot of the funding that is going to be earmarked for their particular focus there versus another program directors focus area. 

I think when you look-- when you take technology and not talk about tech companies and you talk about every day like I'm part of a consortium, I'm part of a consortium of other CIOs here in Northeast Ohio, and I can tell you the number of women that are CIO's at major companies, they may not be the CIO at Facebook, but they are the CIO at a bank. The number of people of color who are maybe CIO for their public school district, or for their city, for City Hall, or for the housing authority, or for that-- So again I think sometimes when we focus on say tech we think about the Googles, and Facebook's, and the Instagram's, and others of the world, but when you talk about technology with Fortune 500 public sector organization and stuff like that it becomes a tad bit more diverse, not fully diverse but at least a tad bit more diverse. 

SAM CAPLAN: So Leon let me ask a question. So you were describing that you're seeing more women and people of color serving in leadership roles like in other areas maybe not focused on technology at a grant making organization but at a school or a bank, what do we need to do as a sector to start bringing more of these, I'm sure highly qualified individuals, into the fold? 

LEON WILSON: That's always a good question and a compelling question because part of it is when you have to introduce that this is-- there is an opportunity in this industry for technologists. I think for many of us-- I didn't go to school for this, and I didn't know that this was an opportunity it was-- I stumbled across it as I told you earlier in the interview, I'm talking with a recruiter. I would have never ventured. I would have been still looking at Fortune 500 companies or looking at public sector organizations like working for the County, working for the city, working for the public library system, things of that nature that are far more visible. 

I mean especially when you start talking about philanthropy, we're a little bit low key. We're not-- you don't see commercials for the MacArthur Foundation running all over the ad. You don't see billboards promoting the Walton Family Foundation. We're kind of low key in that particular state, so how do people know about us? 

SAM CAPLAN: Right. Yeah I think it's definitely a challenge. But listening to the way that you describe it I actually feel like that's a competitive advantage. Some of the best CIOs that I've come across in this sector, like Katie Niemann she worked for the Houston Zoo before becoming the chief information officer of the Houston Endowment I think it is. So you know like it feels like maybe it's actually better for us in terms of philanthropy if we do find people from outside of our sort of walled garden. 

LEON WILSON: Well there definitely is an opportunity because as I said before, for individuals who may be hitting a ceiling where they're currently at or in the industry that they're at to make a lateral move where you get more exposure, more autonomy, more opportunity to do a lot of other things. But that would mean that we'd have to go find them. I always joke, I was listening to this one commentator talk about how when everybody's talking about the argument that what we can't find good people because the pipeline for people of color are so thin, but then they say Yeah but when you're looking for a football player, a basketball player, you can find it in the backwoods of Mississippi without blinking. So sometimes we have to go out and recruit these people. So let's go to where they're at. Let's go to their affinity groups and market and interview for them during doing job fairs and things of that nature as opposed to sitting back and just posting it on LinkedIn, Indeed, or our affinity group advisory boards that they're not part of. 

I was lucky because I was part of the TAG affinity group mailing list that I stumbled across this position at the Cleveland Foundation. Literally, I found it on a TAG advisory board, but after the job posting was wrapping up on the last day and I said, "Whoa, whoa, what about me?" 

SAM CAPLAN: Yeah. 

LEON WILSON: So if we really want it then we have to go after these individuals and we have to go to where they are. 

SAM CAPLAN: Yeah totally agree with you Leon and I applaud the nonprofit sector for all of the discussion that's taking place these days around equity, and inclusion, and access, but at some point as well this has to go beyond writing a resource guide. It has to go beyond like talking about it on the websites and we have to start putting some action behind the words. 

LEON WILSON: Absolutely, absolutely. 

SAM CAPLAN: All right, so Leon I mentioned earlier like I love talking to you because I feel like you are equally interested in innovation and emerging technologies. So let's talk for a moment about the world of crypto, and blockchain, and NFTs, and DAOs, and decentralized finance in the meta-verse, what does all this have to do with the nonprofit sector? 

LEON WILSON: Well, the key-- what I will say is that it is TBD. But here's what I will say. So there's this concept called Amara's law, Amara's law, A -M-A-R-A law and the premise of it is that we tend to over-hype something in its formative years and under hype or undervalue it once it really gets its sea legs. 

SAM CAPLAN: Yeah. 

LEON WILSON: And right now with things like NFT, crypto, blockchain, and so forth, it was so over-hyped in 2019, 2021, and going on that again because it didn't catch right away like lightning, like the internet did, and start and explode it right away because it was commercialized. And you have that super app like email, or that super app like Facebook and stuff like that, or WhatsApp, people now get lukewarm with it. And I think we just need to keep pressuring through. So there is going to be a home for crypto in the non-profit space beyond just taking crypto. There's going to be a role for it. 

We're not quite sure what that is right now because all the case studies and the accidental experiences that we say, hey, we can try this and try this, and now we got something that's truly viable and valuable. There will be a place for NFTs, and nonprofits, and philanthropy. We just haven't really figured it out just yet. We're still in that hype section and hype curve right now. So I can't go out because other people that are true futuristic that can tell you to read the signs and read the signals and here's where we're going all that sort of stuff. I can't predict that, but I know that there's something there. We just have to keep studying it, keep going forward to it, and at some point in time something will click. And the more that we've already studied it, researched it, piloted it, prototype with it, played with it, experimented with it, the better position a particular non-profit or foundation will be once it really does catch fire. 

SAM CAPLAN: Yeah, for sure. So let's dovetail that into the world of community foundations. So I have been really curious to see what's next for the Community Foundation? So if you look back over the last several years, there's been this explosion of DAFs. And it feels to me like community foundations are really competing head to head with Fidelity Charitable, and Schwab Charitable, and 1,000 other DAFs that have all sprung up. So what do community foundations and in particular have to do to be more competitive and to evolve? 

LEON WILSON: Well, two things. One, we can't sit on our laurels and use the same argument that we've always used that about we know the local community better than anybody else. That was always our mantra, is that you're coming and you're going to open up a DAF with the Cleveland Foundation, or with the Silicon Valley Community Foundation, or with the Toledo Community Foundation, or the Boston Foundation, because we know the local community like no one else. But Fidelity doesn't know-- well they might know Boston, but Fidelity doesn't know Tulsa, Oklahoma like Tulsa Community Foundation knows it. That's going to eventually kind of become weaker and weaker with things like big data, artificial intelligence, gleaming all that information where you don't need to be an expert in that local community, you just need to know enough. 

SAM CAPLAN: Right. 

LEON WILSON: And it's going to be-- we're going to be victims of good enough. Where again I don't have to pay that additional price point to place my DAF with your Community Foundation, I can go with a lower price point with Fidelity because they're basing it on volume of transactions and then we will lose out. So we can't setttle-- we can't be too lax about that. That's where again now what we're talking about investing in technology and trying to look and see how the Fidelity's, and the Vanguard's, and others are leveraging technology, and what can we learn from them and how can we kind of replicate that ourselves. Maybe on a smaller scale, but we can kind of keep pace with them so we don't become victims of good enough. 

SAM CAPLAN: Right, right. So you are on the board of directors for TAG. You're on the board of directors for NTEN. I'm not sure if I'm missing any other major organizations out there that are taking advantage of your expertise, but that's pretty fantastic. I'd love to hear what is your experience and in terms of serving on these boards? 

LEON WILSON: Well serving on NTEN board that was where I kind of basically cut my teeth working with nonprofits. When I went to go work in a nonprofit field, I was back in Michigan helping small and mid-sized nonprofits throughout the state of Michigan to leverage technology. So NTEN was my tribe. That's where I went to go figure out what's going on in the field of technology. What kind of tools and solutions were being offered, discount prices, and all that kind of stuff. So I can boil a lot of that down and then talk for the 10 or 15 minutes for the one hour that executive director had time to give me to help inform him or her how they ought to be positioning their technology ecosystem. So I had a long history with NTEN working with them on that standpoint, speaking at a lot of their conferences, helping them out with their conferences, and so forth. 

But because of the work that I was doing, I had exposure to community foundations and private foundations as well. Helping them out and I developed a decent relationship with the Kellogg's, and the Kresge Foundations, and the Skillman Foundation, and CS Mott Foundations on looking at data. Because I was looking at how nonprofits are leveraging data, if you want to know how your grantees are collecting data, what kind of tools they have, their skill sets, then I'm the person to tell you because I'm running all over the state of Michigan. I know what they're using, I know what they're not using. 

So that gave me that exposure to now helping foundations better understand when they want to create some kind of metadata warehouse of information to look at the impact in the state of Michigan. That's where that connection came in. That's where I got introduced to TAG as well because some of my own clients providing back office tech support were your very small community foundations that didn't have staff. I wanted to know, well what kind of tools do Community Foundation use? What's so special about Community Foundations? So that's where I got introduced to the TAG community. And then when I became the CIO of a Community Foundation I immediately jumped in and said, OK now I found another tribe to be part of. 

SAM CAPLAN: My background in terms of working at Grant making organizations has been I worked at Walmart Foundation, I worked at the Walton Family Foundation, these are big organizations. And it just feels when we talk about what's happening in the world of philanthropy tech we tend to center on what's going on at the Gates Foundation, what's going on at the MacArthur Foundation, or the Cleveland Foundation, we're not necessarily looking at what's happening with these grant makers who have a total of seven employees and who are working with nonprofits that have seven employees. I feel like we're in a sense, we're kind of doing them all a disservice. 

LEON WILSON: No you're absolutely right. I mean, I look just to the right and to the left and me, I have a communication one county over, the Lorain Community Foundation, that has a staff of maybe six or seven people, and then you go down South of me I have the Akron Community Foundation they may have a staff of 10 or 12 people. Whereas we're now hovering over 90. Now the technology that they're using probably pales in comparison to the technology that we're using or that we have the opportunity to leverage. When you start talking about things like cybersecurity, my goodness, their cybersecurity budget compared to ours cybersecurity budget is nothing-- it pales in comparison as well. 

So you are absolutely right. And that is one argument that I try to make when we talk about trying to do things like fix the form and do other kind of things that a lot of times when we're talking about the grantee, the nonprofit, they're just not getting dollars from one foundation, from one Community Foundation, they're getting from the city, from the state, especially if they're in mental health, substance abuse, or social services. They're getting more of their money from the government than they are from philanthropy. And we're not going to change their government as far as fixing their form. 

So I try to take a pragmatic approach to that and say OK, unless we hit a certain inflection point where 20% of us or more are all agreeing to do this then the stick-to-it-ive-ness of any of these endeavors are going to be very, very small. Unless you go towards some kind of a cohort model where you're going to pick eight or nine nonprofits and you're going to invest in those nonprofits. And then you're going to tailor your systems and they're going to tailor their systems so that you all can go scale and go fast type of thing. Short of that, then yeah the fact that the top five largest foundations agreed to do something, but they don't fund in Cleveland, they're not involved with the United Ways of America or the local United Way's in greater Cleveland or Detroit or whatever, then I question how much can really-- what kind of impact, what kind of change can really be done. Not discounting it, keep pushing for it, but then I just ask a lot of questions. 

SAM CAPLAN: It makes perfect sense, I don't think that most of us realize how many awards your typical nonprofit receives over the course of a year and how challenging it can be for that nonprofit to manage all of the administrative work of applying for those grants, and providing progress reports, and impact data back to everybody who has given them a handful of dollars to do their work. And so to your point, I don't know what the ultimate answer is here, I think we need the Cleveland Foundations and the MacArthur Foundations of the world to help set the tone. But I also feel like we're really missing out by not taking greater advantage of all of these smaller grant makers as well who are quite frankly are scrappy and their innovative. And they're doing things in a way that is just so much faster than so many of the large grant making organizations that have 50 years of process built up. 

LEON WILSON: And that might be where I'm always interested in looking at things from an inside out perspective. Maybe that is where we need to focus our attention on how can we help the lower-- the next tier of grant makers work with us and do the kind of work that we're doing in leveraging technology and taking advantage of the kind of technologies that we're taking ourselves. 

SAM CAPLAN: Yeah, totally agree. So it's been such a fun discussion and thank you so much for spending the time with me here. I can't wait to see you. I know we're both going to the Social Innovations Summit in DC in a couple of months, So we'll get a chance to hang out. 

LEON WILSON: I will definitely be there. 

SAM CAPLAN: Awesome I will be there too, so hopefully our listeners will track us down in the bar at night and hang out with us and tell us what they thought about this podcast. 

LEON WILSON: Right, well always great chatting with you Sam. 

SAM CAPLAN: All right Leon same to you, my friend. Thank you very much. 

Thanks to you for joining us today. Do check out the episode notes to learn more about Leon, Sam, the Cleveland Foundation, TAG, and NTEN. 

Impact Audio is edited and produced by Jordan Marvin, Laura Steele, and yours truly. Submittable is a cloud-based social impact platform designed to help your team make better decisions and have a bigger impact. We’d love to partner with you to maximize social good and create lasting change through smarter technology—find out more at Submittable.com. And until next time, take good care.