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Steve Lee on a Coalition Approach to Workforce Impact

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Steve Lee, CEO of SkillUp Coalition, discusses how his nonprofit technology platform connects nearly 3.5 million workers without college degrees to career training and job opportunities nationwide. Drawing from his diverse background spanning corporate law, educational technology, and philanthropy, Lee explains the coalition's "data-driven, heart-led" approach that ingests labor market data from partners and tests it with real workers to improve outcomes. He shares insights on navigating AI's impact on gateway jobs like customer service, emphasizing the shift toward skilled trades, advanced manufacturing, and green jobs as more automation-resistant career paths. Lee discusses the importance of balancing national reach with regional customization through 35 localized sites that reflect specific labor market demands, and explains how combining "air game" technology with "ground game" wraparound services creates more effective worker support. The conversation explores practical strategies for building mutually beneficial partnerships in workforce development, with Lee advocating for humility, value-addition, and collective impact as essential elements for scaling upskilling efforts and addressing intergenerational poverty.

Transcript

Julian Alssid: Welcome to Work Forces. I'm Julian Alssid.

Kaitlin LeMoine: And I'm Kaitlin Lemoine, and we speak with the innovators who shape the future of work and learning.

Julian Alssid: Together, we unpack the complex elements of workforce and career preparation and offer practical solutions that can be scaled and sustained.

Kaitlin LeMoine: Work Forces is supported by Lumina Foundation. Lumina is an independent, private foundation in Indianapolis that is committed to making opportunities for learning beyond high school available to all. Let's dive in. A central focus in our consulting practice and on this podcast is practically how to make meaningful connections between the various organizations and resources that exist to help people close gaps and advance their careers.

Julian Alssid: Absolutely, we've seen a surge of new tech products designed to bridge skills gaps, connecting individuals with training programs and with the employers who can hire them. And key to their success are solutions that are designed for and responsive to the needs of the end user.

Kaitlin LeMoine Precisely. And that's why today we're excited to dive into a conversation with a leader who is at the forefront of using technology to connect millions of workers to meaningful career opportunities. Our guest is Steve Lee, the CEO of Skill Up Coalition. Steve has a fascinating career journey that began as a corporate lawyer, then saw him found and successfully exit an educational software company and work at Bain & Company. He then transitioned to the social sector, including a significant role at the Robin Hood Foundation, before taking the helm at Skill Up.

Julian Alssid: Steve brings a blend of business acumen and a deep commitment to social good, and we're looking forward to speaking with him about how to upscale efforts in a world of rapid change, especially with the increasing influence of AI. Since launching Skill Up in 2020, Skill Up's nonprofit technology platform has already connected nearly 3.5 million workers without a college degree to career training and job supports nationwide, and the coalition now includes more than 150 partners. Impressive.

Kaitlin LeMoine: Truly. So Steve, welcome to Work Forces. We're so glad you could join us to share more about these impactful efforts.

Steve Lee: I am so honored and thrilled to be here. Thank you both very much for the current show. I will say my family, says I'm a dork and so, true story and so anyway, just thank you. It's a pleasure to be here and looking forward to the conversation.

Kaitlin LeMoine: Great. Well, as we get started, can you please tell us a bit more about your background and what led you to your work at Skill Up Coalition.

Steve Lee: So as you, as you alluded to. I was in a private sector for a good chunk of, let's say, the first half of my career, but I've always sort of been interested in having some impact on the social side. I had a really good conversation with a nonprofit leader when I was in the private sector, and she said something which I thought was really interesting. She said, Steve, I've been doing this work for 50 years, and I serve young people and adults. And she said to me that when I serve young people, there's a very good chance that 30 years later I'm gonna see the same person to serve their needs. And what that struck me is this idea of not only just poverty, but this idea of intergenerational poverty, where poverty goes to multiple generations. I'm like, damn, this is not good. This is not the country I want to live in. So what the heck can we do about it? And so that's one of the main reasons I joined philanthropy, is to think about a way, in a very small way, obviously, right where I could have some impact, if you will, in a small way, on this idea of improving what I think is one of the biggest scourges in this country is intergenerational poverty and the fact that half of 30 year olds in this country now are worse off than their parents were when they were 30. You know, inflation adjusted, that is a very bad step. All right, that's what, that's what that that's what drives me with the work I do. It's why I came to Skill Up. Because I feel like one of the ways is you can, one of the ways you can address that is, if you have stable wages for good work you have stable families, you have stable kids, and the kids can do better in life. Because every parent in the world, I don't care who you are, rich, poor, you know, Democrat, Republican, urban. It doesn't matter. Every parent wants to carry do better in life, every single parent. So when we're doing a very, very bad job of that. And so that's why I take this work that we do at scope is important, and why the ecosystem is important. So that's the reason.

Julian Alssid: It's really sobering when you see those stats about declining wealth, and we've got to fix this, because we've helped create this mess - our generation, the concentration of wealth. And I mean, we could go on, but tell us a little bit more about who Skill Up serves, who you're looking to serve in this kind of intergenerational approach and the range of initiatives that you've developed.

Steve Lee: We are, we're primarily designed to serve STARS, if you know that terminology, those are Skilled Through Alternative Routes, which is basically folks that don't have a college degree. We have a particular focus on the lower rung of that ladder, right? Those who are maybe on public benefits, those are the most marginalized in this country. And we serve youth all the way to dos, and on this journey, I think the most important thing for this journey for us is the fact that we are a coalition, so it's actually our official name. We're not, we're not Skill Up we’re Skill Up Coalition. That's actually our IRS registered name, and that means a lot to us, because we're a small nonprofit, right? What the hell are we going to do by ourselves? Like nothing, like literally nothing, right? So we can only do something if we work together with some of our core partners. And if you go to our site, you can see some of our core partners. These are folks who are leaders in the field, and we do our best right to add value into that ecosystem. We can talk a little bit more about what value means, but the most important thing for us as an organization is to truly partner for mutual benefit. This is one of what our funders love to say, mutual benefit. It's actually pretty hard to do mutual benefit, to work with others to create collective effect. I can give you examples of that, but that is one of the most important things we can do.

Kaitlin LeMoine : Please say a little bit more about that when you say mutual benefit. Let's dive in there a little bit.

Steve Lee: Yeah. So let's talk about what I think is one of our key jams, right? One of the core value sets that we have, one of our core principles is to be data driven, heart led. I've always liked that term, because as a technology nonprofit, we are driven by data. Obviously, I'll talk about what that means. But everything we do, we hope, is for the benefit of workers, right? And we have workers at scale, and we've learned the time. And so one of the coolest ways that I think we work with partners is on the data side. And let me explain what that means. So we have become a platform for low wage workers, where people are coming to us to some degree with data sets, and what they want to do is they want to test those data sets with real workers to get their worker voice on whether this stuff works or not. So I'll give you some examples. There are some really interesting data sets on the employer side. Groups like American Opportunity Index, which is funded by Burning Glass in partnership with the Schultz Family Foundation. There's a Credential Value of Index, I think that's what it's called. Used to be called EQOS, which has sort of the signals of quality for training programs in America. What these programs, what these data sets have, is really, really good data, but they have no way to surface that data with real workers. And so what we're doing is we're ingesting those data sets, and then we're spitting those data sets into the arms of workers across America, using a skills platform as a vehicle to do that, and then we're learning to see what works for real workers. This is what I call heart led right? What's the worker voice? What are they telling us what works and what doesn't work? And then we're spitting that back into our partners to improve their data sets. So it all comes full circle, this idea of ingestion, spitting out data, learning from data, and going back to the original source as a full circle, that's like, really, really important, I think, in the broader ecosystem. And I think we're one of the few platforms that can actually do that right, because we have technology, we have good UX/UI, we have workers, we can send things out to, and then we can test a real scale, like 10s of 1000s, right? Within a week or two, to have statistically significant data that comes back to us that we can inform the field that's a real value, and that's what that's mutual benefit, like, we're helping our workers, right? And in theory, we're also helping the data sets. That doesn't happen all the time, like mutual benefits, actually pretty hard, but that's one example, Kwsaitlin and how we're thinking about mutual benefit, particularly around benefit, particularly around data, because I think that is probably one of our biggest jams, is the ingestion of data, plus the data driven heart led, right? The ability to access workers and get their workable voice.

Kaitlin LeMoine: That's a complex space in which you're sitting to build that mutual benefit with, as you said, right, like the end users, like the people you're looking to serve, as well as with your data partners.

Steve Lee: Correct.

Kaitlin LeMoine: Living in the middle of that space, I imagine, is exciting and also pretty complicated.

Steve Lee: You know what's interesting? What I've learned is, like, this is gonna get very wonky, but like, data is it's basically just like a bunch of fields. But what's tricky is that you have to match those fields like this is, like, wonky data stuff, and like, actually matching those fields to collect the right information to get out to the right is actually very tricky, right, because there are so many fields. So that's actually the hard work. But once you get there, it can be pretty powerful. In terms of stuff that you learn.

Julian Alssid: So Steve, just sticking with this one a little bit longer. Again.

Steve Lee: Sure.

Julian Alssid: This is the geeking out, because I think our listeners will be very interested. We want to talk about AI and the workforce. But of course, are you using AI in this effort to then sort of mine and collate and organize this data?

Steve Lee: Yeah, we're using AI, I think, so why call this idea of more stuff and better stuff? So this is like, like third grade English, right? And so what we can do with our, with our AI, is the data sets that we have, we can have more of the things that we want. And what I mean by that is that our main call to action for our users is, hey, what's the right career you have? What could work? What career do you want? What job do you want? And three, you probably need some kind of training to get the right credential to get the job. All right? So what training is available to you? So what AI can do is that it can surface up more opportunities that we wouldn't be able to surface up, but for the power of AI. So that's one, and second, we could be better at what we offer. One of the things that we pride ourselves as being high quality, and we curate all the opportunities. And the curation is done a lot by data sets, plus desk research. The desk research can be somewhat replaced by AI, right? So rather than having a human, or in conjunction with a human, you have AI to make that research better, and so you have better stuff that we show up as high quality content, as opposed to just having a human, plus data sets, plus you have more stuff, because there are some things that we're missing, because it's a big country or a small nonprofit, right? And so more stuff, better stuff is not what we're doing in terms of the things that we power. The other thing we're doing around AI is what I call horizontal integration. So as you guys know, the journey from a low wage worker starting to look for a job, to finding the job, can actually be more than just a few inches. It can be miles and miles and miles, right? It takes a long time. It takes months, sometimes years, right? And so if our users stick with us, what we can do with AI, no matter where they are in their journey, you can offer AI as a recommendation, no matter where you are. So your beginning part of the journey, AI will make some kind of recommendation to Julian saying, We think you should do A, B and C, but Kaitlin is further along in her journey and is about to interview for a job. We could offer a different AI experience. So can say, hey, you should think about doing this for an interview, things of that sort. And AI can do that almost like when you do a Google search. Now, you don't see this, you don't see the search results. You see Google AI, overview, right? That's the first thing you see. Similar concept for us, no matter where you are, you're going to get something around AI, and then hopefully that helps you drive to at&t organizations. So that's a horizontal integration, right? And the vertical is more stuff, better stuff.

Julian Alssid: Are the learners, workers, whatever you're calling the clients. Are they staying with you? I mean, you've, you've now, you know, you do have this growing data set.

Steve Lee: It's the trickiest wicket of a direct to consumer platform. You know, unless you're Meta or Google, it's hard for direct to consumer users to stick right. And we have the same issues as others. I always say about roughly half of our users drop off after sort of initial experience and then, but the other half stick around to some manner of form. And the first that's actually pretty good, right? As a direct to consumer, nonprofit, right? So we're actually proud with, like, the half that stick. But what our partners say sometimes, even if they come and they bounce, maybe there's value that you just don't know. They come, they browse a little bit, they leave after 30 seconds, you don't know, you don't know what value you've had. So our friend was like, okay, the fact they don't stick around for you. That's okay, because maybe they have some value just in the 30 seconds that spark an idea, and then they go someplace else. But maybe we sparked an idea. We just don't know that Julian.

Kaitlin LeMoine: Well, and we are living at such a, you know, complex moment with respect to the labor market and the shifts we're seeing there. And I'm curious, Steve, you know, to hear you speak a little bit to that as it pertains to the platform and other initiatives you're working on as well, because I can imagine, you know, part of what you're saying about whether people stick or not, I mean, it has to for sure. That has to do with all these other shifts that are happening in the broader landscape.

Steve Lee: You know, it's funny. One of the things that we think a lot, I think about a lot, is where, where's the puck going? I'm a big hockey fan of all things. And you know, as a kid. I used to follow Wayne Gretzky, and he had like, three eyes in the back of his head. He knew where the puck was going, right? And we're not that, but we try to prognosticate. And there are data sets that do this kind of stuff, right, and there's desk research. Yeah. And so to be very specific about it, in the world of AI, because that is where the puck is going. In fact, that's where the puck is. How do we have a platform that is going to serve the worker now and serve the worker two years from now and five years from now? The thing that's come up most recently, and it's fairly, fairly obvious, is the world of skills, trades, advanced manufacturing, uh, green jobs, things of that sort that have come to the fore recently, one, because there's been a lot of money that's been pumped into through the Biden administration, right? Rightfully so. But also, I think people are realizing that this might be sort of what I call the anti AI, right, as we think about, like, entry level jobs. And we've sort of, there's been research, some recent research through BGI and some others. Let's say, you know, college grads are not getting hired as much in the most recent cycle, in part, maybe because of AI, right? So we don't know what's going to be bounced right because of AI. I happen to think even though some of the jobs that Skill Up has now will be bounced because of AI, and if that's the case, then we shouldn't have those jobs anymore, right? Let's be honest. So we're trying to think about where the jobs are so we think skilled trades, advanced manufacturing, there's a piece of that. We have some pretty big efforts afoot right to do that across America, tied to some big federal federal grants with a couple of key partners, and tied to some community colleges that are doing, I think, really cutting edge work on some of the training aspects around getting people the right credential for some of these advanced manufacturing, green jobs, and I think some of the stuff will be important. Yeah, this is it takes a long time to get this to fruition. We're working on that now, as I want to call the anti AI, right? As we incorporate AI into our specific product experience.

Julian Alssid: As we're trying to hone in on the future and where the puck's going. What are you learning and what are some of the challenges you're facing?

Steve Lee: I think we're learning something. But what I just say, right, yeah, which I think, and this applies to Skill Up, because Skill Up's main jam is to help people get what we call gateway jobs. And the discipline knowledge that Opportunity@Work has created through their STARSs Tear the Paper Ceiling Campaign. The challenge with gateway jobs in the world of AI is, I think some of those gateway jobs ain't gonna be here. Like, I really don't right think about things like, like, a customer service rep. I'm going to use that as an example. That is, that is one of our gateway jobs, at least. I think it is right. You think that's gonna be around three years from now? I don't know. All right, let's say that's the level of scale. So I think what we're learning now is that some of those things ain't gonna be here anymore. The challenge is, if that's the case, what's the alternative? And the deeper challenge is, how do we get a non traditional, marginalized worker into this new future that might have been relatively easy as a customer service rep, right? You can get that without paying a lot of money for short-term training, or we would just get the job without a college degree. Maybe that's feasible, but the other stuff may require a two month credential at community college. It might right, it might cost you $2,000, so how do you get that especially working with marginalized populations? So what does that mean for us? Maybe we need to go up the food chain a little. Maybe work with less marginalized people, maybe that have the need to take a two month, $2,000 course. Maybe I'd rather not do that, because our jam is to serve the hardest to serve population. So I think these are things that are floating in my head. It is like supply, labor, supply, demand issues. It's very tricky, but part of why we exist is to be able to offer things that are of the moment, that are real, viable, and high quality. And I don't think I'm going to use customer service rep, I don't think it's going to be high quality. And if I don't think it'll exist right in three years. So that's a struggle that we work through Julian as best we can.

Julian Alssid: A great example.

Kaitlin LeMoine: Yeah, well, and I would imagine, too, the other piece of this, as you've said, right, this is a coalition effort. And I guess I'm wondering, how do you go about forming and reforming partnerships and coalitions to advance this work in a way that is, you know, kind of timely, and as you're saying, maybe moving where the puck is going, even if we're not all entirely clear exactly where that is. What are some considerations that you take into account as you go about that work?

Steve Lee: I think part of it is that what I hope we do is we go in with some humility. All right, into the conversation if you want partners, because we don't have all the answers, and sometimes we are not the right partner, so you should kick us out, and we should be humble enough to recognize that we shouldn't be part of that big kids table, right? That's true. And so, so. But if, if we think we should be, I think we hope to come in in this mindset of value add you. In some manner or form. So think about some of the things I find, like a market opportunity index, or what used to be called EQOS, right? We came in there thinking we can add some value because we have an asset that maybe you don't have, which is this ability to test with real users using electronic experience, but it's actually going to make your data sets better. So I suppose I always try to come in with humility, with value add, with mutual benefit. And I think the fourth thing is, is someone doing this already? We are not the only a career navigation platform, right? There are many, many, many, many right across the globe, as you guys know, some of them are friends, right? So the question is that that's already being done by somebody else, then it makes no sense for us to bring it right? No value add. I think that's actually really because we live in a world where we don't have enough time to compete. We just got to do our thing. You do your thing. Well, if you want us great, or if we add value, if not, they kick us out, right? And that's perfectly fair, with a mindset of humility, right? As opposed to being a little bit, you know, angry about it.

Julian Alssid: Don't get angry. So on the so on the topic of coalitions, a lot of our work involves, you know, navigating, building these kind of, these coalitions and I was, I was looking at your May newsletter or your LinkedIn announcement about your newsletter, and you talked a little bit about the data and the distinction between national and regional or local coalitions. And I know you kind of play in both spaces. Can you? Can you speak to that at all?

Steve Lee: Of course, regional is really important for us for very various reasons. One less important thing, this is where the funders sometimes might be right. Let's be honest, right? Sometimes you need money to do some stuff, right? There are a lot of regional funders, but that's not, that's not the most employing, yes, we have a national presence, right? True. If you're in North Dakota, where we don't have reasonable experience, you can take the value of Skill Up right in terms of things that might be virtual or remote things, great, but everything, as we know, I knew you all know this right, happens at the regional level. It's where the labor market goes, it's where the employers are, it's where the people and their families are. And so we have built, I want to say, 35 regional sites, and I think the value of those regional sites is that they're very bespoke to the region. So the things we offer, whether it's the right career, the right job or the right training, is all tied to labor market demand in that region. So when you go to Los Angeles, right, you're going to see a very different experience, right? If you go to my home state, home city of New York, versus some of our other 30, 30, plus users, right? And that's really, really valuable, because people in Los Angeles don't get don't give a crap about me, or vice versa. I don't give a crap about Los Angeles, right? I hate the Dodgers, right? And the Lakers. I just care about New York, although New York kind of sucks too, to be honest, when it comes to sports, but New York, New York is its own beast, right? And it's its own, its own employment, right? And all employers, and that's the experience that we offer that's rich and deep. The other thing it brings that is often difficult for us is a ground game. So we have a really good air game, aka technology, which we think we do, what we miss sometimes is the ground game with local on the ground organizations to do really meaningful work. And if we can better connect our users beyond just the air game into a ground game where they can get direct support for things like wraparound support service, things like that, that's really, really, really valuable air game plus ground game. And some of our partners are looking for that combination. You can't get that in North Dakota. I'm just making up North Dakota, right? You can't, because we don't, we don't, we don't have a ground game, right? And that's really powerful. So you get local assets important for the user, and if we can work it out, you get a ground game of support services that better enrich the experience for workers in that community.

Kaitlin LeMoine: Yeah, I love this notion of the air and ground, right? Because there's also the way that the learnings from the ground game could impact the air game too, right? And so having the ability to operate at both of those levels just makes so much good sense.

Steve Lee: Totally, totally agree.

Kaitlin LeMoine: There's like endless lessons that you're pulling from, from some of that regional work.

Steve Lee: Exactly.

Kaitlin LeMoine: To inform what you do, more broadly.

Steve Lee: Exactly.

Julian Alssid: I was just gonna say, I mean, you know, we need maximum flexibility, right? Because everything we're talking about is like, people, machines, national, local. It's like, it's a very fluid system. So we need all the tools to bring to the table.

Steve Lee: Indeed, indeed we do so.

Kaitlin LeMoine: Steve, drawing from your experiences and pulling on, I guess, all of the different threads we've been talking through today. What practical steps can our audience take to become forces in scaling up, upskilling, and workforce development efforts. What are some practical takeaways you might recommend for others looking to do this kind of work?

Steve Lee: Reach out, right? I'm easy to find. To find me on LinkedIn right, and let's try to work together, right, because you just never know, right? So I think that's my first advice, is reach out and because who knows, right, what great things can happen. The other thing I would say, and that this is more of my, like, my philanthropic experience when I was about managing here in New York City, is to do something this makes any sense you run a nonprofit in a particular region, approach, maybe approach things with this idea of like humility, value added, and mutual benefit, if that makes any sense, because I think people, people want to work together. This is also, if I'm being honest, it's where the stakeholders and the funders are going. In part, if you want to get the resources and nonprofit to do great work, more philanthropists are asking for joint mutual efforts beyond just your own effort. And so I think it behooves us as an ecosystem to think collectively together, just like philanthropy doing is, you know, recently they've done much more. And I like this about having, like this collective effort stuff. There's like an AI collective funder group. There's like a skills trades collective group. There's an impact collective group, right? When I used to do philanthropy, I didn't, I didn't give a crap about other other funders. I just wanted to be in my own sandbox, right, Robin Hood, right? But now people will think that's really good, right? Think the same as a tactical organization is if you can work together with others for some level of mutual benefit, even though it's hard because you have to give a little bit, I think money, it's a little easy to get money, if that makes any sense, right? That's a very tactical money, because people care about money, right?

Kaitlin LeMoine: Those are two pretty foundational - provide a lot of direction - in those two recommendations. So thank you for that.

Steve Lee: Thank you. Great question. I'm really, really, really honest about like, working together, like, and that's the thing that's really important. And some of the coolest partners we've had have just been through random conversations.

Julian Alssid: Well, that comes through loud and clear, Steve, and you know, it's been such a pleasure talking with you as always today. And you know, we look forward to continuing the conversation. Really appreciate you taking the time.

Steve Lee: It's my pleasure. Thank you both for all that you guys do, and I'll make a plug for you guys. I think you guys have been awesome. I think about one of the best podcasts out there in America for workforce so thank you guys for what you do.

Kaitlin LeMoine: Thank you so much.

Julian Alssid: Very nice of you.

Kaitlin LeMoine: That's all we have for you today. Thank you for listening to Work Forces, we hope that you take away nuggets that you can use in your own work. Thank you to our sponsor, Lumina Foundation. We're also grateful to our wonderful producer, Dustin Ramsdell. You can listen to future episodes at Work Forces dot info or on Apple, Amazon and Spotify. Please Subscribe, Like and share the podcast with your colleagues and friends.

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Steve Lee, CEO of SkillUp Coalition, discusses how his nonprofit technology platform connects nearly 3.5 million workers without college degrees to career training and job opportunities nationwide. Drawing from his diverse background spanning corporate law, educational technology, and philanthropy, Lee explains the coalition's "data-driven, heart-led" approach that ingests labor market data from partners and tests it with real workers to improve outcomes. He shares insights on navigating AI's impact on gateway jobs like customer service, emphasizing the shift toward skilled trades, advanced manufacturing, and green jobs as more automation-resistant career paths. Lee discusses the importance of balancing national reach with regional customization through 35 localized sites that reflect specific labor market demands, and explains how combining "air game" technology with "ground game" wraparound services creates more effective worker support. The conversation explores practical strategies for building mutually beneficial partnerships in workforce development, with Lee advocating for humility, value-addition, and collective impact as essential elements for scaling upskilling efforts and addressing intergenerational poverty.

Transcript

Julian Alssid: Welcome to Work Forces. I'm Julian Alssid.

Kaitlin LeMoine: And I'm Kaitlin Lemoine, and we speak with the innovators who shape the future of work and learning.

Julian Alssid: Together, we unpack the complex elements of workforce and career preparation and offer practical solutions that can be scaled and sustained.

Kaitlin LeMoine: Work Forces is supported by Lumina Foundation. Lumina is an independent, private foundation in Indianapolis that is committed to making opportunities for learning beyond high school available to all. Let's dive in. A central focus in our consulting practice and on this podcast is practically how to make meaningful connections between the various organizations and resources that exist to help people close gaps and advance their careers.

Julian Alssid: Absolutely, we've seen a surge of new tech products designed to bridge skills gaps, connecting individuals with training programs and with the employers who can hire them. And key to their success are solutions that are designed for and responsive to the needs of the end user.

Kaitlin LeMoine Precisely. And that's why today we're excited to dive into a conversation with a leader who is at the forefront of using technology to connect millions of workers to meaningful career opportunities. Our guest is Steve Lee, the CEO of Skill Up Coalition. Steve has a fascinating career journey that began as a corporate lawyer, then saw him found and successfully exit an educational software company and work at Bain & Company. He then transitioned to the social sector, including a significant role at the Robin Hood Foundation, before taking the helm at Skill Up.

Julian Alssid: Steve brings a blend of business acumen and a deep commitment to social good, and we're looking forward to speaking with him about how to upscale efforts in a world of rapid change, especially with the increasing influence of AI. Since launching Skill Up in 2020, Skill Up's nonprofit technology platform has already connected nearly 3.5 million workers without a college degree to career training and job supports nationwide, and the coalition now includes more than 150 partners. Impressive.

Kaitlin LeMoine: Truly. So Steve, welcome to Work Forces. We're so glad you could join us to share more about these impactful efforts.

Steve Lee: I am so honored and thrilled to be here. Thank you both very much for the current show. I will say my family, says I'm a dork and so, true story and so anyway, just thank you. It's a pleasure to be here and looking forward to the conversation.

Kaitlin LeMoine: Great. Well, as we get started, can you please tell us a bit more about your background and what led you to your work at Skill Up Coalition.

Steve Lee: So as you, as you alluded to. I was in a private sector for a good chunk of, let's say, the first half of my career, but I've always sort of been interested in having some impact on the social side. I had a really good conversation with a nonprofit leader when I was in the private sector, and she said something which I thought was really interesting. She said, Steve, I've been doing this work for 50 years, and I serve young people and adults. And she said to me that when I serve young people, there's a very good chance that 30 years later I'm gonna see the same person to serve their needs. And what that struck me is this idea of not only just poverty, but this idea of intergenerational poverty, where poverty goes to multiple generations. I'm like, damn, this is not good. This is not the country I want to live in. So what the heck can we do about it? And so that's one of the main reasons I joined philanthropy, is to think about a way, in a very small way, obviously, right where I could have some impact, if you will, in a small way, on this idea of improving what I think is one of the biggest scourges in this country is intergenerational poverty and the fact that half of 30 year olds in this country now are worse off than their parents were when they were 30. You know, inflation adjusted, that is a very bad step. All right, that's what, that's what that that's what drives me with the work I do. It's why I came to Skill Up. Because I feel like one of the ways is you can, one of the ways you can address that is, if you have stable wages for good work you have stable families, you have stable kids, and the kids can do better in life. Because every parent in the world, I don't care who you are, rich, poor, you know, Democrat, Republican, urban. It doesn't matter. Every parent wants to carry do better in life, every single parent. So when we're doing a very, very bad job of that. And so that's why I take this work that we do at scope is important, and why the ecosystem is important. So that's the reason.

Julian Alssid: It's really sobering when you see those stats about declining wealth, and we've got to fix this, because we've helped create this mess - our generation, the concentration of wealth. And I mean, we could go on, but tell us a little bit more about who Skill Up serves, who you're looking to serve in this kind of intergenerational approach and the range of initiatives that you've developed.

Steve Lee: We are, we're primarily designed to serve STARS, if you know that terminology, those are Skilled Through Alternative Routes, which is basically folks that don't have a college degree. We have a particular focus on the lower rung of that ladder, right? Those who are maybe on public benefits, those are the most marginalized in this country. And we serve youth all the way to dos, and on this journey, I think the most important thing for this journey for us is the fact that we are a coalition, so it's actually our official name. We're not, we're not Skill Up we’re Skill Up Coalition. That's actually our IRS registered name, and that means a lot to us, because we're a small nonprofit, right? What the hell are we going to do by ourselves? Like nothing, like literally nothing, right? So we can only do something if we work together with some of our core partners. And if you go to our site, you can see some of our core partners. These are folks who are leaders in the field, and we do our best right to add value into that ecosystem. We can talk a little bit more about what value means, but the most important thing for us as an organization is to truly partner for mutual benefit. This is one of what our funders love to say, mutual benefit. It's actually pretty hard to do mutual benefit, to work with others to create collective effect. I can give you examples of that, but that is one of the most important things we can do.

Kaitlin LeMoine : Please say a little bit more about that when you say mutual benefit. Let's dive in there a little bit.

Steve Lee: Yeah. So let's talk about what I think is one of our key jams, right? One of the core value sets that we have, one of our core principles is to be data driven, heart led. I've always liked that term, because as a technology nonprofit, we are driven by data. Obviously, I'll talk about what that means. But everything we do, we hope, is for the benefit of workers, right? And we have workers at scale, and we've learned the time. And so one of the coolest ways that I think we work with partners is on the data side. And let me explain what that means. So we have become a platform for low wage workers, where people are coming to us to some degree with data sets, and what they want to do is they want to test those data sets with real workers to get their worker voice on whether this stuff works or not. So I'll give you some examples. There are some really interesting data sets on the employer side. Groups like American Opportunity Index, which is funded by Burning Glass in partnership with the Schultz Family Foundation. There's a Credential Value of Index, I think that's what it's called. Used to be called EQOS, which has sort of the signals of quality for training programs in America. What these programs, what these data sets have, is really, really good data, but they have no way to surface that data with real workers. And so what we're doing is we're ingesting those data sets, and then we're spitting those data sets into the arms of workers across America, using a skills platform as a vehicle to do that, and then we're learning to see what works for real workers. This is what I call heart led right? What's the worker voice? What are they telling us what works and what doesn't work? And then we're spitting that back into our partners to improve their data sets. So it all comes full circle, this idea of ingestion, spitting out data, learning from data, and going back to the original source as a full circle, that's like, really, really important, I think, in the broader ecosystem. And I think we're one of the few platforms that can actually do that right, because we have technology, we have good UX/UI, we have workers, we can send things out to, and then we can test a real scale, like 10s of 1000s, right? Within a week or two, to have statistically significant data that comes back to us that we can inform the field that's a real value, and that's what that's mutual benefit, like, we're helping our workers, right? And in theory, we're also helping the data sets. That doesn't happen all the time, like mutual benefits, actually pretty hard, but that's one example, Kwsaitlin and how we're thinking about mutual benefit, particularly around benefit, particularly around data, because I think that is probably one of our biggest jams, is the ingestion of data, plus the data driven heart led, right? The ability to access workers and get their workable voice.

Kaitlin LeMoine: That's a complex space in which you're sitting to build that mutual benefit with, as you said, right, like the end users, like the people you're looking to serve, as well as with your data partners.

Steve Lee: Correct.

Kaitlin LeMoine: Living in the middle of that space, I imagine, is exciting and also pretty complicated.

Steve Lee: You know what's interesting? What I've learned is, like, this is gonna get very wonky, but like, data is it's basically just like a bunch of fields. But what's tricky is that you have to match those fields like this is, like, wonky data stuff, and like, actually matching those fields to collect the right information to get out to the right is actually very tricky, right, because there are so many fields. So that's actually the hard work. But once you get there, it can be pretty powerful. In terms of stuff that you learn.

Julian Alssid: So Steve, just sticking with this one a little bit longer. Again.

Steve Lee: Sure.

Julian Alssid: This is the geeking out, because I think our listeners will be very interested. We want to talk about AI and the workforce. But of course, are you using AI in this effort to then sort of mine and collate and organize this data?

Steve Lee: Yeah, we're using AI, I think, so why call this idea of more stuff and better stuff? So this is like, like third grade English, right? And so what we can do with our, with our AI, is the data sets that we have, we can have more of the things that we want. And what I mean by that is that our main call to action for our users is, hey, what's the right career you have? What could work? What career do you want? What job do you want? And three, you probably need some kind of training to get the right credential to get the job. All right? So what training is available to you? So what AI can do is that it can surface up more opportunities that we wouldn't be able to surface up, but for the power of AI. So that's one, and second, we could be better at what we offer. One of the things that we pride ourselves as being high quality, and we curate all the opportunities. And the curation is done a lot by data sets, plus desk research. The desk research can be somewhat replaced by AI, right? So rather than having a human, or in conjunction with a human, you have AI to make that research better, and so you have better stuff that we show up as high quality content, as opposed to just having a human, plus data sets, plus you have more stuff, because there are some things that we're missing, because it's a big country or a small nonprofit, right? And so more stuff, better stuff is not what we're doing in terms of the things that we power. The other thing we're doing around AI is what I call horizontal integration. So as you guys know, the journey from a low wage worker starting to look for a job, to finding the job, can actually be more than just a few inches. It can be miles and miles and miles, right? It takes a long time. It takes months, sometimes years, right? And so if our users stick with us, what we can do with AI, no matter where they are in their journey, you can offer AI as a recommendation, no matter where you are. So your beginning part of the journey, AI will make some kind of recommendation to Julian saying, We think you should do A, B and C, but Kaitlin is further along in her journey and is about to interview for a job. We could offer a different AI experience. So can say, hey, you should think about doing this for an interview, things of that sort. And AI can do that almost like when you do a Google search. Now, you don't see this, you don't see the search results. You see Google AI, overview, right? That's the first thing you see. Similar concept for us, no matter where you are, you're going to get something around AI, and then hopefully that helps you drive to at&t organizations. So that's a horizontal integration, right? And the vertical is more stuff, better stuff.

Julian Alssid: Are the learners, workers, whatever you're calling the clients. Are they staying with you? I mean, you've, you've now, you know, you do have this growing data set.

Steve Lee: It's the trickiest wicket of a direct to consumer platform. You know, unless you're Meta or Google, it's hard for direct to consumer users to stick right. And we have the same issues as others. I always say about roughly half of our users drop off after sort of initial experience and then, but the other half stick around to some manner of form. And the first that's actually pretty good, right? As a direct to consumer, nonprofit, right? So we're actually proud with, like, the half that stick. But what our partners say sometimes, even if they come and they bounce, maybe there's value that you just don't know. They come, they browse a little bit, they leave after 30 seconds, you don't know, you don't know what value you've had. So our friend was like, okay, the fact they don't stick around for you. That's okay, because maybe they have some value just in the 30 seconds that spark an idea, and then they go someplace else. But maybe we sparked an idea. We just don't know that Julian.

Kaitlin LeMoine: Well, and we are living at such a, you know, complex moment with respect to the labor market and the shifts we're seeing there. And I'm curious, Steve, you know, to hear you speak a little bit to that as it pertains to the platform and other initiatives you're working on as well, because I can imagine, you know, part of what you're saying about whether people stick or not, I mean, it has to for sure. That has to do with all these other shifts that are happening in the broader landscape.

Steve Lee: You know, it's funny. One of the things that we think a lot, I think about a lot, is where, where's the puck going? I'm a big hockey fan of all things. And you know, as a kid. I used to follow Wayne Gretzky, and he had like, three eyes in the back of his head. He knew where the puck was going, right? And we're not that, but we try to prognosticate. And there are data sets that do this kind of stuff, right, and there's desk research. Yeah. And so to be very specific about it, in the world of AI, because that is where the puck is going. In fact, that's where the puck is. How do we have a platform that is going to serve the worker now and serve the worker two years from now and five years from now? The thing that's come up most recently, and it's fairly, fairly obvious, is the world of skills, trades, advanced manufacturing, uh, green jobs, things of that sort that have come to the fore recently, one, because there's been a lot of money that's been pumped into through the Biden administration, right? Rightfully so. But also, I think people are realizing that this might be sort of what I call the anti AI, right, as we think about, like, entry level jobs. And we've sort of, there's been research, some recent research through BGI and some others. Let's say, you know, college grads are not getting hired as much in the most recent cycle, in part, maybe because of AI, right? So we don't know what's going to be bounced right because of AI. I happen to think even though some of the jobs that Skill Up has now will be bounced because of AI, and if that's the case, then we shouldn't have those jobs anymore, right? Let's be honest. So we're trying to think about where the jobs are so we think skilled trades, advanced manufacturing, there's a piece of that. We have some pretty big efforts afoot right to do that across America, tied to some big federal federal grants with a couple of key partners, and tied to some community colleges that are doing, I think, really cutting edge work on some of the training aspects around getting people the right credential for some of these advanced manufacturing, green jobs, and I think some of the stuff will be important. Yeah, this is it takes a long time to get this to fruition. We're working on that now, as I want to call the anti AI, right? As we incorporate AI into our specific product experience.

Julian Alssid: As we're trying to hone in on the future and where the puck's going. What are you learning and what are some of the challenges you're facing?

Steve Lee: I think we're learning something. But what I just say, right, yeah, which I think, and this applies to Skill Up, because Skill Up's main jam is to help people get what we call gateway jobs. And the discipline knowledge that Opportunity@Work has created through their STARSs Tear the Paper Ceiling Campaign. The challenge with gateway jobs in the world of AI is, I think some of those gateway jobs ain't gonna be here. Like, I really don't right think about things like, like, a customer service rep. I'm going to use that as an example. That is, that is one of our gateway jobs, at least. I think it is right. You think that's gonna be around three years from now? I don't know. All right, let's say that's the level of scale. So I think what we're learning now is that some of those things ain't gonna be here anymore. The challenge is, if that's the case, what's the alternative? And the deeper challenge is, how do we get a non traditional, marginalized worker into this new future that might have been relatively easy as a customer service rep, right? You can get that without paying a lot of money for short-term training, or we would just get the job without a college degree. Maybe that's feasible, but the other stuff may require a two month credential at community college. It might right, it might cost you $2,000, so how do you get that especially working with marginalized populations? So what does that mean for us? Maybe we need to go up the food chain a little. Maybe work with less marginalized people, maybe that have the need to take a two month, $2,000 course. Maybe I'd rather not do that, because our jam is to serve the hardest to serve population. So I think these are things that are floating in my head. It is like supply, labor, supply, demand issues. It's very tricky, but part of why we exist is to be able to offer things that are of the moment, that are real, viable, and high quality. And I don't think I'm going to use customer service rep, I don't think it's going to be high quality. And if I don't think it'll exist right in three years. So that's a struggle that we work through Julian as best we can.

Julian Alssid: A great example.

Kaitlin LeMoine: Yeah, well, and I would imagine, too, the other piece of this, as you've said, right, this is a coalition effort. And I guess I'm wondering, how do you go about forming and reforming partnerships and coalitions to advance this work in a way that is, you know, kind of timely, and as you're saying, maybe moving where the puck is going, even if we're not all entirely clear exactly where that is. What are some considerations that you take into account as you go about that work?

Steve Lee: I think part of it is that what I hope we do is we go in with some humility. All right, into the conversation if you want partners, because we don't have all the answers, and sometimes we are not the right partner, so you should kick us out, and we should be humble enough to recognize that we shouldn't be part of that big kids table, right? That's true. And so, so. But if, if we think we should be, I think we hope to come in in this mindset of value add you. In some manner or form. So think about some of the things I find, like a market opportunity index, or what used to be called EQOS, right? We came in there thinking we can add some value because we have an asset that maybe you don't have, which is this ability to test with real users using electronic experience, but it's actually going to make your data sets better. So I suppose I always try to come in with humility, with value add, with mutual benefit. And I think the fourth thing is, is someone doing this already? We are not the only a career navigation platform, right? There are many, many, many, many right across the globe, as you guys know, some of them are friends, right? So the question is that that's already being done by somebody else, then it makes no sense for us to bring it right? No value add. I think that's actually really because we live in a world where we don't have enough time to compete. We just got to do our thing. You do your thing. Well, if you want us great, or if we add value, if not, they kick us out, right? And that's perfectly fair, with a mindset of humility, right? As opposed to being a little bit, you know, angry about it.

Julian Alssid: Don't get angry. So on the so on the topic of coalitions, a lot of our work involves, you know, navigating, building these kind of, these coalitions and I was, I was looking at your May newsletter or your LinkedIn announcement about your newsletter, and you talked a little bit about the data and the distinction between national and regional or local coalitions. And I know you kind of play in both spaces. Can you? Can you speak to that at all?

Steve Lee: Of course, regional is really important for us for very various reasons. One less important thing, this is where the funders sometimes might be right. Let's be honest, right? Sometimes you need money to do some stuff, right? There are a lot of regional funders, but that's not, that's not the most employing, yes, we have a national presence, right? True. If you're in North Dakota, where we don't have reasonable experience, you can take the value of Skill Up right in terms of things that might be virtual or remote things, great, but everything, as we know, I knew you all know this right, happens at the regional level. It's where the labor market goes, it's where the employers are, it's where the people and their families are. And so we have built, I want to say, 35 regional sites, and I think the value of those regional sites is that they're very bespoke to the region. So the things we offer, whether it's the right career, the right job or the right training, is all tied to labor market demand in that region. So when you go to Los Angeles, right, you're going to see a very different experience, right? If you go to my home state, home city of New York, versus some of our other 30, 30, plus users, right? And that's really, really valuable, because people in Los Angeles don't get don't give a crap about me, or vice versa. I don't give a crap about Los Angeles, right? I hate the Dodgers, right? And the Lakers. I just care about New York, although New York kind of sucks too, to be honest, when it comes to sports, but New York, New York is its own beast, right? And it's its own, its own employment, right? And all employers, and that's the experience that we offer that's rich and deep. The other thing it brings that is often difficult for us is a ground game. So we have a really good air game, aka technology, which we think we do, what we miss sometimes is the ground game with local on the ground organizations to do really meaningful work. And if we can better connect our users beyond just the air game into a ground game where they can get direct support for things like wraparound support service, things like that, that's really, really, really valuable air game plus ground game. And some of our partners are looking for that combination. You can't get that in North Dakota. I'm just making up North Dakota, right? You can't, because we don't, we don't, we don't have a ground game, right? And that's really powerful. So you get local assets important for the user, and if we can work it out, you get a ground game of support services that better enrich the experience for workers in that community.

Kaitlin LeMoine: Yeah, I love this notion of the air and ground, right? Because there's also the way that the learnings from the ground game could impact the air game too, right? And so having the ability to operate at both of those levels just makes so much good sense.

Steve Lee: Totally, totally agree.

Kaitlin LeMoine: There's like endless lessons that you're pulling from, from some of that regional work.

Steve Lee: Exactly.

Kaitlin LeMoine: To inform what you do, more broadly.

Steve Lee: Exactly.

Julian Alssid: I was just gonna say, I mean, you know, we need maximum flexibility, right? Because everything we're talking about is like, people, machines, national, local. It's like, it's a very fluid system. So we need all the tools to bring to the table.

Steve Lee: Indeed, indeed we do so.

Kaitlin LeMoine: Steve, drawing from your experiences and pulling on, I guess, all of the different threads we've been talking through today. What practical steps can our audience take to become forces in scaling up, upskilling, and workforce development efforts. What are some practical takeaways you might recommend for others looking to do this kind of work?

Steve Lee: Reach out, right? I'm easy to find. To find me on LinkedIn right, and let's try to work together, right, because you just never know, right? So I think that's my first advice, is reach out and because who knows, right, what great things can happen. The other thing I would say, and that this is more of my, like, my philanthropic experience when I was about managing here in New York City, is to do something this makes any sense you run a nonprofit in a particular region, approach, maybe approach things with this idea of like humility, value added, and mutual benefit, if that makes any sense, because I think people, people want to work together. This is also, if I'm being honest, it's where the stakeholders and the funders are going. In part, if you want to get the resources and nonprofit to do great work, more philanthropists are asking for joint mutual efforts beyond just your own effort. And so I think it behooves us as an ecosystem to think collectively together, just like philanthropy doing is, you know, recently they've done much more. And I like this about having, like this collective effort stuff. There's like an AI collective funder group. There's like a skills trades collective group. There's an impact collective group, right? When I used to do philanthropy, I didn't, I didn't give a crap about other other funders. I just wanted to be in my own sandbox, right, Robin Hood, right? But now people will think that's really good, right? Think the same as a tactical organization is if you can work together with others for some level of mutual benefit, even though it's hard because you have to give a little bit, I think money, it's a little easy to get money, if that makes any sense, right? That's a very tactical money, because people care about money, right?

Kaitlin LeMoine: Those are two pretty foundational - provide a lot of direction - in those two recommendations. So thank you for that.

Steve Lee: Thank you. Great question. I'm really, really, really honest about like, working together, like, and that's the thing that's really important. And some of the coolest partners we've had have just been through random conversations.

Julian Alssid: Well, that comes through loud and clear, Steve, and you know, it's been such a pleasure talking with you as always today. And you know, we look forward to continuing the conversation. Really appreciate you taking the time.

Steve Lee: It's my pleasure. Thank you both for all that you guys do, and I'll make a plug for you guys. I think you guys have been awesome. I think about one of the best podcasts out there in America for workforce so thank you guys for what you do.

Kaitlin LeMoine: Thank you so much.

Julian Alssid: Very nice of you.

Kaitlin LeMoine: That's all we have for you today. Thank you for listening to Work Forces, we hope that you take away nuggets that you can use in your own work. Thank you to our sponsor, Lumina Foundation. We're also grateful to our wonderful producer, Dustin Ramsdell. You can listen to future episodes at Work Forces dot info or on Apple, Amazon and Spotify. Please Subscribe, Like and share the podcast with your colleagues and friends.

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