At one point in the conversation, Cary Strange, the CEO of PayOnward, says something that instantly cuts through the noise around artificial intelligence. The goal is not to replace people. It is to free them up. That simple line reframes everything that follows, and it feels especially relevant for credit unions that are hearing nonstop talk about automation, efficiency, and disruption but still care deeply about human relationships.
Cary joins Sarah Snell Cooke on The Credit Union Connection with the kind of background that gives weight to his perspective. He has built payment platforms, worked deep in fintech and spent years alongside banks and credit unions solving real operational problems. What becomes clear very quickly is that this is not a conversation about shiny tech. It is about the narrowing gap between what small businesses need day-to-day and the tools that many financial institutions still offer.
What makes the discussion engaging is how practical it stays. Cary keeps coming back to the same idea: Small businesses are not thinking in terms of platforms or products. They are thinking about getting paid, paying bills and knowing whether they will be short on cash next month. When those answers are hard to find, frustration sets in. When they are easy and proactive, trust deepens.
There is also a refreshing honesty in how Cary talks about AI. He compares this moment to the early days of the internet, when everything had to be labeled as web-based. Eventually, that stopped being the headline and simply became how things worked. His point is that AI will follow the same path. Credit unions that treat it as background infrastructure rather than a headline feature may be the ones that benefit most.
Sarah presses on the human side of this shift, especially the fear many employees feel when new technology enters the picture. Cary does not brush that aside. He acknowledges the cultural change while arguing that the bigger risk is leaving people stuck doing repetitive work that adds little value. The opportunity, as he sees it, is giving staff better tools so they can spend more time having meaningful conversations with members and business owners.
What makes the conversation worth watching is how much of it lives in the nuance. Cary connects the dots between AI, payments, small business behavior and credit union culture in a way that feels grounded. You can hear where the friction actually shows up, where opportunity quietly exists, and where assumptions start to break down. It is the kind of discussion that lands differently when you hear it unfold in real time.
NOTE: The below AI-generated transcript of the video might not be 100% right, but are any of us really?
Sarah Cooke
Alrighty. Hello and welcome everyone. My name is Sarah Snell Cooke, of course, I am your host at The Credit Union Connection. I am joined today by Cary Strange, welcome.
Cary Strange
Thank you very much. Glad to be here.
Sarah Cooke
Yeah, glad to have you. And now Cary is the CEO of PayOnward and other things. I’ll let him go into that. So Cary, why don’t you go ahead and introduce yourself, tell us a little bit more about PayOnward also.
Cary Strange
Well, sure, thanks for having me here. Sarah, really appreciate it, and I’m the CEO of a company called Pay onward. And we’re part of Black Dragon Capital, which is a private equity firm focused on kind of disruptive technologies that help strengthen communities. So we do a lot of business in the credit union field. I’ve been part of Black Dragon and pay onward for just under a year, so I’m still kind of new in this business, and I think we’ve talked about that a little bit before, but I’ve spent most of my career in various FinTechs. I’ve built an issuer processor, one of the leading prepaid and debit processors in the nation. I’ve worked in prepaid, built out expense management solutions quite a bit, and a lot of the work we’ve done, you know, in those previous companies, a lot of those have been alongside banks and credit unions. So we’ve, we’ve really spent a career helping kind of the members and the business side of things. When you’re looking at credit unions and solutions and what really became clear, and I kind of lead this into kind of my overall experience, but what, what really became clear in all of those types of businesses I’ve been in is the strong relationships that credit unions have with our communities right and our ability To build tools to support those both the business members and the consumer members, has been a thrill to do, but we really believe a lot of that hasn’t kept pace right, that that’s the genesis of pay onward, and I think we’ll talk about later in the conversation, but that’s something that’s really been passionate about. What we’ve done is really working with those credit unions and small businesses. And as we talked to these credit unions, you know, there were gaps in solutions that kept coming up over and over again and that’s really what took my experience in the FinTech world, our experience in selling in and providing solutions in the credit union industry. And we really realized that, you know, small businesses that work with credit unions, you know, they’re not just looking for platforms or products. They want those relationships. You know they want. They want a financial institution that’s going to be there and meet their needs, these guys are not thinking in terms of products and platforms. They’re trying to figure out how to get paid, how to make money, how to pay bills, trying to figure out where they stand financially, right? And when those things get disconnected, it creates friction, and we believe we’ve helped solve that friction. I think my experience that’s helped us come in and working with those credit unions, helping them to modernize kind of the business side of the house, and how they address their small business market, and getting more commercial business in the door. And so everything we built, you know, everything I’ve done in the past, and everything we built here at PayOnward, comes from problems we’re seeing in the field, right? And so those are based on kind of real conversations we have for credit unions and their CEOs, and in real conversations with the businesses those communities, you know, trying to run their business.
Sarah Cooke
Right, solving real world problems, not just playing with tech for the sake of tech. And so speaking of which, I’ll ask the big question, if you know the answer to this, you wouldn’t be on the call with me right now. But how do you see AI reshaping the credit union business overall?
Cary Strange
Yeah, um, I mean, AI is a big word right now, right? I mean, everybody’s talking about it. A lot of people think that AI is kind of a race to replace people, right? So, so you hear that on the news, you hear it everywhere you go, it’s people are going to be losing their jobs to AI. That’s not the goal, you know? I mean, we built our product and platform based on our AI and I know, no, we’re not here to talk just about our product, but, but the goal is not to just replace people, right the do. The goal is really to do something better than what’s being done today for a credit union. That might mean improving how they interact with their. Member base, right? It might. It might mean helping to surface products that are kind of better aligned with a member of business needs and surface that product right when they need it. Right? That’s, that’s some of the things that AI can do. It might be to help that business or member do something that they normally couldn’t do without calling their branch, for example, and the intuitiveness of AI can help them accomplish that, and those are just part of it. But so in the in the end, I think it’s about freeing people up, not replacing people, right? So it means less time on doing repetitive tasks, and more time on really having meaningful conversations. And that’s what we’re trying to do is, is generate those conversations and things between the credit union and the member in the businesses with within the overreaching credit union industry. You could already see this happening in a lot of ways, and you’ve probably seen all the news, but, but as part of Black Dragon, you know, we’ve got a number of credit unions that have invested or partnered with the black dragon ecosystem. And as an example, and I think all of these are public, if somebody wanted to look them up. But, you know, for example, schools first, which is a partner of our parent company, Black Dragon. They invested in a company called zest AI to improve lending decisions. Right? So through AI under underwriting and California Credit Union, that’s another black dragon partner has launched a virtual assistant right to provide 24 by seven member support and again, we’re not talking about replacing people, because they may not have provided that 24/7 support before, and now they’re able to do that through using AI and without having to call branch managers and whatever. They’re able to provide real, tangible support that’s meaningful. And then another one of our black dragon partners all to one, you know, they implemented an AI-powered digital assistant right as part of their lending experience to help, kind of guide people through the borrowing process. So I think when AI is done right, it kind of falls in the background. And if you think about it, and maybe a question to you, I don’t know, but if you think about it, fast forward, I’m aging myself a little bit here, but Fast Forward, back in the in the mid to late 90s, when the late 90s, when the internet was just coming out, like when we were building products, everybody was talking about, you know, it’s web based and internet based, and we’re going to be on the internet. So everything was about that. And I think that’s where we are with AI like even we market it as AI-powered or AI-driven, but in the near future, you know, it’s just going to be ubiquitous, part of everything we do. It’s part of the infrastructure, right? So we’re not going to be focused on the AI itself. We’re going to be focused on the result that a brings us as part of the underlying infrastructure. So we’re in a really neat time right now, but, but at some point, AI will, I think it’s going to kind of fade into the background as far as the talking points, right? And it just becomes a part of how we do business and I think that’s what we’re trying to build as well. They just need a smoother, more responsive experience, and AI can help get them there.
Sarah Cooke
Yeah, yeah, absolutely. How do you how do you help credit unions? I mean, obviously, like you mentioned, some employees are scared. They’re scared. And obviously this is not only, you know, scared of, you know, potentially losing their job, but it’s a cultural change as well inside the credit union. Can you talk a little bit about that, and how you see credit unions kind of easing that shift?
Cary Strange
Yeah, but listen to the shift. The shift is being made. It’s scary to a lot of people. It’s exciting to a lot the people that are the forefront of building and investing and then even implementing, you know, when you look at the credit union, their tech teams, I mean, it’s exciting to these, these groups of people, because they know the value and the power of some of these new solutions and what they’re able to do, but it’s scary to a lot of other people. You know the shift when you start looking at, I mean, could it? Could it cost people jobs? Well, it could, but I think the way a lot of the credit unions are starting to implement it, that’s not what you’re going to see. You’re going to see, it’s going to make people more productive and more efficient and better able to serve their members and their small business members in a way that they couldn’t before. And I think that’s what needs to be kind of pushed to the forefront, is, is not to be afraid of it. It’s this the same thing. I’m going to keep using that analogy this. Same thing of the internet, you know that took away some jobs, but it didn’t displace a lot of the jobs in the internet like the online banking was fantastic, and it allowed people to access the stuff that they normally couldn’t get access to. And then branches and credit unions and the branches you know, rallied around that and figured out, well, let’s make the in person more valuable, and we’re able to do more, in some cases, in the branch, because the basic function of somebody just checking their balance is automated now, right? You don’t have to call the branch anymore to do that. The same thing has happened with AI, right? So to pay, to pay a bill, to move money, you know, it’s going to be automated, and it’s going to be predictive, where people know when you need to meet money and how you need to move money in the least, least cost available to move money in certain ways. You know, those are things that are going to be automated at some point soon. They’re already starting to be automated, but it’s going to be completely automated. You know, the paying your bills. I mean, it’s just going to be done and done for you. And I think credit unions are starting to embrace that, and so I think it’s a positive thing, but it definitely is a cultural shift that a lot of people are having to make. I think the people, again, on the technology side, have already made that shift to a large extent, but the rest of the employees, at the grassroots level, the people that are dealing with the members, they’re going to have to really start understanding how these tools can benefit their business.
Sarah Cooke
I mean, it can help certainly make jobs easier as well, rather than, you know, the mind-numbing, repetitive kind of stuff you’re referring to earlier, yeah, and so let’s get a little more specific. Can we talk specifically about payments, payments tech, since that’s really what you’re into, how is that evolving? And I know we could talk about, you know, everything from blockchain to, you know, the Fed now and on and on and on, but talk a little, you know, go a little bit deeper into payments tech specifically?
Cary Strange
I’ll hit just maybe a couple of points in kind of the trends of what’s going on in payment tech, especially around the credit union. We’ve already talked about AI a little bit. I mean, obviously that’s one of the biggest, biggest trends. And where AI is really starting to show up is kind of in the flow of a credit union’s business around payments, I think that’s one of the areas that is showing up a lot right now. Everything kind of gets lumped into the category of AI and I’ll spend a minute kind of explaining that. And then there’s some other, I think, trends that are happening, but what a lot of people call AI, it may really be machine learning, which is, you know, kind of a building block of AI. So, if you think about a machine learning allows systems to kind of learn data, spot patterns, make predictions without being programmed, you know, for every one of those different scenarios. And that’s what’s really neat about kind of inserting this machine learning and AI pieces into the business, but, but if you think about how that impacts things, that’s what makes things like the payment rounding and fraud detection right and what we do on the pay onwards side, which is from the business side of things, when you start looking at cash flow forecasting, it makes it like really accurate, right? Because you’re not just relying on, number one, a person to do that, and number two, you’re not relying on a system, a static system. So now you have this learning behind the scenes that says, you know if these things happen, and if these things happen, or if these things are going to happen, we’re going to make decisions based on that, right? That’s what that machine learning does, and then the AI makes those decisions. So I think that’s a trend that’s not going to stop throughout 2026 and so we’re excited about that piece, and like we talked about for I think it’s just going to be part of the underlying infrastructure at some point. But from a payment standpoint, I think, you know, one of the shifts is not just about moving money, it’s about how you move money. It’s about timing, visibility, control. And again, I’m talking specifically about the small business side that credit unions address. Businesses already know that they can get paid fast, right? They know certain scenarios that they can get paid fast, but many of those businesses are struggle to integrate it kind of those different payment methods. Into their existing workflow, and they know it’s there. They don’t know how to integrate it. And this goes back to even the member side. There’s a lot of cool functionality out there. There’s a lot of cool payment vendors out there. How do you take what they have and really integrate it into a credit union’s core workflow that’s going to be meaningful either for that small business or the member, that’s one of the questions, and that that’s a that’s something we talk about payment trends, that’s something people are trying to figure out. And there’s been a lot of PR, even in this first two weeks in the credit union industry, around vendors trying to solve that problem. And a good example of something that we’re dealing with is the request for payment feature. You know, instead of sending an invoice, a small business sending an invoice and just waiting for somebody to maybe pay them, the request for payment shows up ready to approve and pay. You know, it’s that nudge. It’s kind of like when you get a personal Venmo request that says, Hey, pay me today, and here’s, here’s the ways you can do that, you know, that’s made its way into invoicing and fed now, and the RTP, they already support it, right? So they report, support the request for payment, and we’re integrating those things into the pay onward business suite. And then another trend is kind of the pay-by-bank feature. It incorporates, you know, the ACH and the RTP and other rails, and just allows somebody to do a very quick, real-time payment kind of bank-to-bank. And I think moving that money from one count to another is not new, but integrating into the workflow is what’s new, right? And what people are having to figure out and hopefully that makes sense. It kind of have. I’ve explained that but, but that’s part of what we’re trying to do. So while these things are not new to credit unions, you’d be surprised, many credit unions either haven’t or they don’t know how to integrate them those different payment methods in a way that truly benefits their customers or their members. So I think that those are like three or four things of where things are going this year. And there’s so many things when you’re talking about payments, but I think those are things that are really on the front of the minds of credit unions.
Sarah Cooke
Yeah, yeah. As a small business owner, I know that all sounds very valuable to me, cash flow in particular, projecting, yeah.
Cary Strange
Wouldn’t it be nice if you could just push a button and all that that takes care of itself, like literally, that’s what we’re that’s what we’re trying to solve.
Sarah Cooke
And we’re seeing a lot of credits getting into business lending. It feels like lately, in particular, we’re seeing credit unions buy banks just to jumpstart their programs. Why do you think this is happening now? What do you think is the impetus for this?
Cary Strange
Well, I would have to come at it more from a kind of a payment in the operating side for running a business. But I think the direction is becoming clear. Why that’s happening. I think commercial lending has among credit unions have, has really exploded lately. I think I don’t have the stat sitting in front of me, but it was, it was over $180 billion the balances for commercial lending. And I think what’s driving it is simple. I think consumer products are not as profitable as they used to be. I think that’s one of the, one of the things, I mean, we’re selling a small business solution. So they, they’re telling us that they need, you know, additional profit centers and way to attract those businesses in. So I think the consumer products aren’t quite as profitable as they used to be, and I also think that business relationships are sticky, right? So, when you get a business in the door, it becomes a very valuable relationship for a long period of time. Is is not a one time transactional basis. These guys, once they, once, they jump into a credit union. They stay around for a long time. And, business members, they don’t just get, you know, they don’t just borrow one time. They bring deposits, they bring payments, they bring other types of services. And business lending is one of those, and it really allows that credit union to kind of upsell into that business and the business lending is one of those. So, and then finally, I think when a when a credit union is supporting kind of how a business runs day to day, lending becomes kind of a natural extension of that relationship, instead of a standalone product, right?
Sarah Cooke
So I think that’s a really important piece when you talk about the business lending and what’s driving it, yeah, for sure. And then you can also potentially get their personal business, and maybe their employees’ business, and that kind of stuff, I think, yeah, yeah, it makes sense. And one of the things that you mentioned a bit ago talking about the nudges, like, not only predictive analytics that you’re talking about. About, but also kind of shaping the way the end user, the business, the consumer, whoever behaves. Can you go in a little more detail about that?
Cary Strange
Well, I think, I think when you, when you talk about shaping how they behave, again, I think you want to a credit union is trying to figure out how to insert themselves into the daily life of a small business and a member and, and, you know, I can look at my own, my own, Simon, I’ve got an account with the National Bank and an account with the credit union here. And, I’m going to be frank. I mean, the National Bank has a way of making sure that, as I’m making decisions in my daily life, they’re serving me offers. And I may not need it all the time, but you know what, when I do need it, it’s always there, you know, for whatever reason. So they’ve managed to figure out, figure out how to, how to how to put those offers for lending, for credit, for other types of services, auto loans, they put them in front of me right where I need it. And that’s one of the dilemmas credit unions are trying to solve and that goes back up to the first several questions we talked about. I think that’s where AI is going to come in and help credit unions, because a lot of times they don’t have the resources or the technology capacity to compete with some of the big banks, but the way in which artificial intelligence is allowing these products to work. It’s leveling the playing field. It’s allowing them to be able to do things that they normally could never have done. And just in the last 12 months, you could have a small credit union that can compete with a national bank in a lot of those areas, from business intelligence and taking that business intelligence to predictive analytics and taking that to serving offers or providing those things right when they need it or how they need it. So it’s really leveling the playing field. So I think that’s, I think that answer your question, but to address those consumer and business concerns, you have to, number one, have the products and services, and number two, you have to get them in front of those people when they need them in the right way.
Sarah Cooke
Yeah. And, I mean, we’ve, spoken previously to your solution is looking not only to help the credit union, help the business, but also just to help the business run better. It’s not strictly about one thing or another. Can you talk a little more about that?
Cary Strange
Yeah, you mean specifically about my product. Correct about pay on, Yep, yeah, I can, and if I could go back to the previous question real quick, and I’ll play that into the product. And, you know, as I was thinking about that, you know, awareness is key when it comes down to offering products and maintaining business and you’re a business owner, I’m a business owner. And you know, our goal is to figure out how to, how to get that business owner to think of a credit union first, right? Whenever they need something. It’s like we should be thinking about it. They have better service and better people and better products. There’s no reason why we should be thinking about the credit union and they often have lower rates. They have better approval rates. I mean, we could go on and on, but for some reason, even I’m guilty of that, I don’t that’s not the first place I look sometimes, right and, and I don’t know why that is, but I think a lot of it has to come down to awareness and experience with that. So, so that kind of parlays into the product that we are building and pay onward has built a product that we believe strengthens, kind of both sides of the relationship. So inherently, we’re a payment company, but we’re focusing on right now, on our what’s called our business suite of products. And we built a suite of solutions that we think kind of challenges small deals with the challenges that small and mid-sized businesses deal with every week and we have an account receivable module. We have a business bill pay module, and we built those. These are not the old school ways of doing things. We built these using AI. We talked about the buzzwords. We built these utilizing AI. We’ve got machine learning in the background. Everything we’ve done is inherently built on the AI infrastructure. So this is not an old Legacy product that we’re just laying on, you know, an agent or something on top of that. We’ve literally built this to run itself, and that’s the underlying goal. So the idea is the credit union can white-label these solutions, they can fully integrate them into their digital. Experience, and we believe it increases the stickiness of that relationship. And ultimately, what that does it brings in more deposits, it brings in more revenue, and it gives them those upsell opportunities that we’ve been talking about, right? It really, it really puts the forefront, puts a credit union on the forefront of those SMBs every day, because every day, they’re logging in and they’re utilizing these tools from the credit union and so we think we’re best positioned to kind of serve the credit union market in that way. But if I don’t know how much time we have, if so, I could go through a couple of use cases of kind of what we’re doing in our product. Let me give you one. Real quick. Sure. Give me one, but, but as an example, kind of tying back to one of the earlier questions, we could combine the account data. So if you think about the account data at the credit union and third party sources, so if a small business has four different accounts and four different financial institutions, we can aggregate all of that account data. We know what their upcoming receivables and payables are, right. So we have all of that data we can integrate with third parties like the QuickBooks and dynamics and other stuff. So we can we have a complete holistic view of what the receivables and payables are, and from there, we can project a real-time cash flow. So we know, not just today. We know what their cash flow is going to look like next week, two weeks from now, three weeks from now, and that’s where you start getting that predictive stuff that you talked about, the predictive analytics. And so using our underlying AI engine, a credit union, can see that business, for an example, is likely going to be short on cash in three weeks, right? So based on this holistic view of what’s going on, this business is going to be short on cash. And so that insight creates kind of a natural lending opportunity, right? That’s what we’re talking about. So with the big banks, what I’m used to is I’m always being hit. I mean, here’s a credit card, credit card, credit card, or here’s a, here’s a lending opportunity instead the so instead of the business, like I used to do, right? The business way the last second, and they’re like, Oh, I’m going to be short. I got to go get a credit card. I can have it in 24 hours, and then I can, I can use that credit instead that the credit union already knows this three weeks in advance. And if it’s a small business, it can be automated. If it’s large business, you know, an account manager can give that business a call and whatever, you know, you can be as personal or as impersonal as you want it to be, but the way we built this thing is the credit union is going to know what’s going on and being able to serve the needs of that member or small business, and that’s ultimately what we want them to do, is serve that need. So we think we’ve, we built a really cool tool from ground up using AI. We think we’re, we’re going to be automating a lot of the task in AR and bill pay. It’s going to be autonomous, like once the system learns your preferences and learns the importance and the priority of the different payables, etc, it’s going to run itself. You know, it’s going to, it’s gonna pay the bills by itself, without your interaction. It’s gonna have the receivables taken care of and do things, make decisions on those receivables to get that in money and faster, which is what small business want to do. And the goal is to make those processes as autonomous as possible, while keeping that credit union right in the middle, right? That’s ultimately, what we want, is that credit unions to study right in the middle of that relationship. So we think we’ve got a really cool tool, and credit unions are responding and, you know, we think it’s going to be something that, as we continue to grow, we’re going to see a lot of traction, you know, in the credit unions on this.
Sarah Cooke
And I want to, I want to see, I want to go back just a little bit something you touched on about not everybody thinks of a credit union first for business services, business lending specifically. But, you know, I found data from the Fed that said that 7% of business credit applicants go to credit unions just 7% despite them actually approving a higher percentage of loans than regional banks and big banks. So how do we rectify this?
Cary Strange
Yeah, again, I think it comes down to awareness and experience. I think if a business owner doesn’t think of a credit card or credit union first, or if that process feels harder or maybe less familiar, maybe a better word than what they’re used to, that approval rate doesn’t even matter, right? I mean, I didn’t know that, you know, I didn’t know that the credit union may approve me at a better rate. I don’t think the average, the average person or small business knows that and so I don’t think that percentage ever comes into play in a lot of cases. Because, you know, I could go, I could go out and talk to my, you know, my 10 friends and I bet out. 10 of them, nine of them wouldn’t even think of going to a credit union, right? And so the question is, how do we, how do we change that? And again, we think we’re, we’re found a mouse trap to say, if we can grab those small businesses, if we can increase the commercial business, like you said, that’s going to inevitably lead to more members. Because I think when they see the value of those services, just like I’ve done, they’re going to switch from the big national bank to a credit union, personally, you know, because it makes sense to do that. But ultimately it comes back, I believe it comes back to exposure and presence. So if a credit union is part of the business, how the business operates every week, it’s much more likely to be top of mind when that credits actually needed.
Sarah Cooke
I agree. All right, well, I always offer my guest final thoughts. What would you like to leave our credit union audience with today?
Cary Strange
I probably wrap up the call by saying I don’t know. Businesses are going to keep expecting experiences that feel that feel easy. You know, we both, again, run small businesses. I think we expect an experience with our banker credit union that’s modern, that’s easy, but we want to feel the value of that relationship right. So I think the institutions that do those things well and make it simple for businesses providing real value, better information, lower cost, you know, whatever that means, value-added services, those, those guys are going to continue to grow and our goal with PayOnward. You know, as part of the broader Black Dragon ecosystem, we’ve got a lot of companies that also help credit unions. I think we’re in a strong position to help those credit unions build and maintain and monetize those commercial relationships, and that ultimately adds that value that I think, that I think is needed in that credit union space, awesome.
Sarah Cooke
Well, thank you so much for your time today. Cary, appreciate it.
Cary Strange
Yeah, I appreciate you having me on and thanks so much.