How Fintech is Modernizing Field Services – Jacob Olins of WorkWave

Episode Overview

Jacob Olins is the SVP & GM, Fintech at WorkWave, a leading software platform for field service businesses across industries like landscaping, pest control, and HVAC. Jacob has deep roots in traditional finance, having previously held roles at Citibank and JP Morgan, where he worked with large institutional clients. His move to WorkWave was driven by a desire to bring those high-level financial tools and insights to smaller businesses that have historically been underserved.

At WorkWave, Jacob leads fintech strategy, product innovation, and partnerships, with a focus on automating core financial functions like digital payments, subscriptions, financing, and sales tax compliance. His team recently launched an upgraded payments platform that provides real-time business insights and subscription onboarding tools aimed at increasing both revenue and valuation.

Jacob Olins is passionate about making fintech accessible to mom-and-pop businesses and giving them the tools to operate like enterprise players. He believes that simplifying workflows, embracing digital transformation, and focusing on customer experience can empower service-based businesses to grow sustainably—and eventually exit profitably.

Episode Transcript

Jacob Olins: You’re the software provider and you’re like, hey, you know, I know every time you make a sale what the sales tax is, and I know that it’s a, you know, pain in the butt to to pay out, to have a process where you got to go pay sales tax every month. And I know that if you, you know, miss that or you miss a file, you’re going to get a penalty. Oh, and by the way, I can also be the one who’s collecting this money for you. You know, you’re at the software platform. You’re in this really interesting position to say, well, look, why don’t I just do sales tax for you, right? And I’ll set you up with a bank account at that. That is just for your sales tax portion of your funds.

Kevin Rosenquist: Hey there. Welcome to PayPal, where we bring you conversations with the trailblazers shaping the future of payments and fintech. My name is Kevin Rosenquist. Thanks for listening. Fintech is transforming industries across the board. But one space that often flies under the radar is field service businesses. Think everything from pest control to HVAC, to landscaping. A lot of businesses in this space are still focused on cash or even, dare I say, checks. And many also continue to rely on paper invoices. So how can we modernize their operations? My guest today is Jacob Olin, VP of Fintech at WorkWave, a company that has been a driving force in software solutions for field service industries with a focus on fintech work, Wave is helping businesses optimize their cash flow, improve customer payments and manage financial operations in an increasingly digital world. Today, we’re going to dive into the intersection of fintech and field service businesses, explore the unique financial challenges these industries face, and we’ll look at how technology is shaping the way service businesses operate and grow. So please welcome Jacob Olin. So fintech is often associated with banking investment and consumer payments. But but you guys at WorkWave you’re applying these innovations to field service businesses. Why is fintech becoming such a crucial part of this industry?

Jacob Olins: Yeah, I think that’s a great question. You know, I think that, , like a lot of industries that maybe are made up of a lot of, you know, local owned,  businesses, smaller businesses, , they just typically haven’t had, like, the same love and attention and access to tools that,  maybe some of the larger, you know, more,  obviously technologically forward, , types of industries have, , and so certainly, like we see that in field services, we see a lot of our customers are small and medi sized, family owned,  businesses. And, you know, they’re out there focused on doing a field services job. They’re out there focused on making a lawn look really nice or making sure that, you know, you don’t have any termite damage or,  you got a rodent infestation totally eliminated. So, like, modern fintech tools, things like buy now, pay later, the blockchain, what have you are kind of like buzzwords that don’t have any resonance. I think typically in like how these businesses think about what’s going to improve their day to day. Yeah, it’s.

Kevin Rosenquist: A good point because.

Jacob Olins: Like, you know.

Kevin Rosenquist: We recently had a guy that quote a damage to our fence outside and like, you know, we had someone put in some sod last summer. And like all these different service parts, it’s historically cash check clunky invoicing, paper invoices just really. Yeah, kind of outdated, you know, how are you seeing, you know, digital payments transforming these businesses and what’s and what’s driving the shift?

Jacob Olins: Yeah, I guess like anything like you see a specter, you see a spectrum of like adopters. You see some, you know, businesses that are early adopters and that are like, hey, you know, I know how my Amazon experience works. I know how you know, checkout on Instagram works. Like, how do I get to a more,  how do I get my business to operate more like that, right? They sort of like seeing the future. And I think you see other businesses that are kind of used to doing things the way that they’ve always done things. I think, you know, one of the key things is like, you get the early adopters and you get them excited and they’re kind of out there asking for innovation to begin with. And then you develop like these really powerful case studies with some of those early adopters and like, you know, my favorite,  statistic that we observe in our business is that this is like a real number. We see our customers that are high adopters of our WorkWave payments. So that’s all of our integrated digital payments capabilities. We see them consistently grow at 55% of a faster rate than all of the companies in our portfolio that are not actively adopting.

Jacob Olins: And it’s sort of like the threshold is like 70%, you know, 70% of your accounts receivable is going through this integrated payments. That’s where you really see the fastest growth. But it’s pretty linear. You know, the lower adopters, they grow slower, the higher adopters they grow faster. And like what the underlying reason for that is like you’re through integrating this stuff into the software that you’re using to run your business. You take a lot of these manual processes, operational processes out of the business and lets the, you know, the leaders of the business focus a lot more of their time on the things that they’re really good at, which is like getting new customers, providing a really great service. , you know, you’re making it obvious to the business owner, hey, when you’re selling to a new customer, you know, encourage them to get onto a subscription plan. When you are, you know, getting them to confirm, like, yes, I want this service. Make sure that you’re capturing a card. Like, when you do that, you know, we’re storing that for you. We’re keeping it secure, and then we’re putting it on auto pay. And so now you know you’re in the same game as Netflix.

Jacob Olins: This is a set it and forget it subscription. That customer is using your service. You know you know that the money’s coming in. And so you know that you’re going out and doing your service on a regular basis. That makes such a difference. , you know, and then we like to reinforce some of that stuff like we use account updater, right. So if the card gets expired or lost or stolen, we’re able to keep that service subscription live, we’re able to keep that money flowing. That makes such a difference, right? Not to have to go chase customers. Hey, your card’s expired or you owe me money. All those uncomfortable conversations, we can just help our customers avoid those. They sell a lot more. They focus on the things that they’re really good at and that that whole finance operation becomes a lot simpler. So yeah. So I guess going back to your question then we’ve got those stories, then we can go out and and use that kind of example to the customers that maybe aren’t as forward thinking or, you know, still prefer cash because they can feel it, or a check because they can they can see it or it’s because they’ve always done things.

Kevin Rosenquist: Operation, there’s a good chance they’ll have some sort of, you know, digital payment option or something like that, where and if it’s more of a one man show or a mom and pop or something like that, a lot of times more, they still rely on older stuff. Do you find that? Is it fear or or or not understanding tech? Is it just if it ain’t broke, don’t fix it, you know, because honestly, if you’re talking about the customer experience, it seems like a bad idea not to get current with the digital trends when it comes to payments. So you’re going to fall behind a little bit. And I could see people like having a problem with that. Unless you’re just the best ever at what you do and it doesn’t matter anyway. But what do you see as the biggest reasons for the resistance to moving to a digital platform for field service industries?

Jacob Olins: Yeah. I mean, how I’ve always done things, you know, my business isn’t big enough to really need that. And there’s, you know, it’s like what you’re getting at is there might be some objection to, like, starting to adopt software to manage your business, period. And then like another set of objections to like, hey, do I want all of my payments processing flowing through this same software? Or do I really want to move to like credit card acceptance and, and that kind of thing? , you know, I think like for, for businesses that are kind of doing over half $1 million a year, like everybody gets, you know, yeah, you got to accept payment the way that your customers want to pay. I think below that $500,000 threshold, then you get more of the, you know, this is the way I’ve always done things. And you also get like,  well, I’m collecting cash and I get, you know, $100 every time I sell $100 worth of service. And, like, credit card processing is expensive. And so, you know, it’s true. It costs you more technically to accept a credit card, but that customer convenience makes you sell to a lot more customers and makes it a lot easier to collect a subscription. And that is another thing that, , you know, especially in some of our industries, is a change that, like the whole industry has been going through and continues to go through, is like a lot of these businesses historically were not subscription businesses.

Jacob Olins: , and so, you know, if you’re kind of changing your business model from doing a lot of one off services to doing subscription services, that that’s a really obvious point in time to be like, oh, yeah, you know, the penny drops a little bit more easily on like, yeah, obviously I want to get a payment method on file. I need auto pay. Like that whole operational process. I wouldn’t have an ability to do that. Now. I’ve got the ability to do that. , so I think that, you know, that’s a tailwind for sure. And a good just industry trend for the field services industry. But yeah I mean I think you know like if you’re a really small operation you don’t have a lot of employees. There’s less to manage. You feel less risk. You know your technician’s going to go and collect the cash. They’re going to bring it back to you. You know, as soon as your organization scales a little bit, you know, and you’re hiring somebody that you don’t have a ten year relationship with.  it makes a lot more sense that they don’t have cash in their pocket that they could walk away with at the end of the day.

Kevin Rosenquist: Good point. That’s a really good point. And also, like I think about it in a cash flow way too. Right. Because you know, if you invoice people, if you’re taking cash on the spot, that’s one thing. If you’re invoicing people, it’s a little more unpredictable. You can have cash flow issues, you know, due to delayed payments. And then all of a sudden you’re got bills piling up and all that. When you’re talking to potential customers, is this something that you pitch as an idea that fintech can help solve?

Jacob Olins: Yeah. The cash conversion cycle is so much better. I mean, your days to cash is like a couple of days, maybe exactly the same day as you provided the service versus, you know, in arrears by 30 days or more. , yeah, 100%. You know, I think like,  you got to have some amount of accounting and financial sophistication just to know that that matters.

Kevin Rosenquist: Yeah. That’s a good point. That is a real good point. And also I still think I think too, like you, sometimes I feel like the old school mentality is not as as good at addressing or realizing time is money kind of. So, you know, you know, the amount that you can save by streamlining using technology to streamline your operations. The time you get back to your point earlier about going out and getting business and servicing your customers properly and all that, you know, I feel like sometimes some of the old school mentality, people kind of lose sight of that or don’t see it at all. Yeah.

Jacob Olins: Yeah I think 100% .

Kevin Rosenquist: Embedded finance, I’d like to talk about that. It’s obviously a hot topic in fintech and in payments and, you know, allowing businesses to integrate financial tools directly into their operations. It’s something we talk about on this show quite often. How does that fit into the future of the field service businesses?

Jacob Olins: I think it’s huge. I mean, I think like I think the big picture story here is like, you know, nobody’s out there shouting about how awesome their user experience is with their bank and like, how well, you know, their bank understands how their business runs and therefore is able to help them manage cash. And like the banks, they just don’t have the context, right? They need context whenever they’re selling or trying to provide additional financial services. There’s a whole like implementation process that is like heavily giving me all the context I need to underwrite you. I need to, you know, know how your business is growing over x, y, z number of years. I need to know who your suppliers are. Right. So like, give me this whole huge data dp and then I’m going to try to, you know, analyze all that data to understand your business a little bit better. And then here’s kind of, you know, an account structure I would recommend or a loan or, you know, a loan that I could offer you or a payable solution. , and so that’s pretty painful. I think the beauty of and the kind of the promise of embedded finance and like, we’re in the really early days and hopping around a little bit, but like, you know, it’s this $13 trillion industry that’s kind of like trying to, you know, that is probably a lot larger.

Jacob Olins: There’s probably a lot of greenfield in that. , but it’s also like, how do we migrate this into the businesses in their context so that they can get a lot more use out of that? And so, you know, some of that 13 migrates into the software platform and then that overall 13 grows. Then. , anyway,  I think like the you know, the beauty of that is if you’re the software provider and you’re like, hey, you know, I know every time you make a sale what the sales tax is, and I know that it’s a, you know, pain in the butt to pay out, to have a process where you got to go pay sales tax every month. And I know that if you, you know, miss that or you miss a missed file, you’re going to get a penalty. Oh, and by the way, I can also be the one who’s collecting this money for you. You know, you’re at the software platform. You’re in this really interesting position to say, well, look, why don’t I just do sales tax for you, right? And I’ll set you up with a bank account at that. That is just for your sales tax,  portion of your funds.

Jacob Olins: And then I’ll go and I’ll pay that sales tax for you and like, you know what? I’ll even throw in, like, a guarantee on this, like, I’m the one liable if you get an if I messed this up, you know, any penalties? I’m the one who pays that. I think that’s like a pretty extraordinary proposition. And that’s sort of like surface level, you know, where embedded finance can go, you know, then you start to say, okay, well, what are the other funds?  What are the other things that you’re doing with your funds? And how do you get sort of from, , helping a customer collect, you know, on the payment side to helping them, you know, spend and budget and, you know, sort of maximizing the efficiency of how that, I don’t know, $1 million a year of revenue turns into 150,000in payroll and $ 100,000 in accounts payable expense. And , you know, hopefully,  larger and larger percent of that profit. And then, you know, how can you help them manage that profit so that they’re reinvesting where they want or taking it off the table or they want? Yeah. So I, you know, like that’s a bit of a rambling response. But it’s a.

Kevin Rosenquist: Big.

Jacob Olin: Topic.  Yeah it’s a big topic. And , it’s just it’s really complicated today and like, you know, nobody’s kind of guiding you through it. I think as a business owner, you’re figuring it out for yourself.

Kevin Rosenquist: Yeah, I kind of wonder about that sometimes because, I mean, you know, with personal stuff, you see embedded finance a lot as far as apps having financial aspects to them and all that. But, you know, with businesses, you know, especially going back to what I was talking about with the mom and pops being nervous, like trying to get them on board with some of these complicated systems isn’t always easy. How do you balance that? Innovation. But also, you know, keeping the friction low. And also of course, you’ve got security and you’ve got all these different aspects you have to balance, you know, how how does that work, especially when working with people in an industry that might be more resistant to technological change than say, you know, like, I don’t know, a startup or a tech startup or something like that.

Jacob Olins: Yeah I mean, I, I think you got to start with, like, solving a really specific problem and making that obvious and really plugged in to the way that they’re doing their business and using your system a lot about it is like, how are you embedding that in their software so that their workflow is not changing? It’s just like, you know, you’re rather than doing these two processes, you’re doing, you know, one thing and two things are getting done. So, you know, you’re doing accounts receivable, you’re looking at your daily transactions. Oh, and now you’re observing taxes are getting paid out. You know, your sales tax is getting paid out on your behalf, for example, , which.

Kevin Rosenquist: Is huge because that’s such a pain in the butt but sales tax of a huge a in the.

Jacob Olins: But yeah the smaller you are the more hats you’re wearing. Doesn’t mean that there’s like fewer tasks to do. It just means that there are fewer people to do all those tasks. So , yeah, I think it’s really about like, you know, there’s I think the other thing that we hear a lot like the American, like regional and commercial banking industry is still pretty strong like relationship banking, small businesses. And so, you know, despite the lack of technology or innovation that a lot of these banks offer,  customers when it comes to money. Like that’s something that like trust is really important. And so having a, you know, hand being banker can be a really big differentiator, especially like, you know, where you want to have an answer, you want to talk to somebody to get an answer. It’s not as straightforward as, you know, typing something into a chat bot or right, you want some real hand advice. So, you know, I then like with all that in mind, I don’t think it’s our job or software platforms job to like to try to replace that. I think it’s just like, is there some obvious use case? Our system, the data that we’re already getting could make something that’s complicated, a lot less complicated. And that’s the thing that we focus on.

Kevin Rosenquist: Yeah. You guys have a range of business solutions. You know what? What are the unique tools that WorkWave brings to the table that sort of differentiates you from other service business platforms?

Jacob Olins: Sure. Yeah. One of the things that I’m super excited about is just on our fintech innovation roadmap. You know, we’ve done a lot of work this year, and we’re coming to market with a new version of our payments platform. And so it does a couple of things right. It’s really like looking at, you know, all of our customers’ revenue holistically. And it’s saying, you know, hey, , you’re providing a lot more insights around the data that, you know, we’re already helping our customers collect generating for our customers. So we’re able to tell a customer, you know, hey, take this million dollar business example like, hey, it looks like, you know, 40% of your business is on a subscription. You know, that’s great that you’ve gotten that far. , but, you know, here’s 60% of your customers and your and your sales that aren’t on a subscription. , you know, here’s the the increased value that we’d expect you to get from bringing on new customers onto a subscription who are used to, you know, paying you one off for services, you know, kind of click on this graph and here’s a list of these customers and the outreach that you should do. , and then, you know, further evolving that into, oh, do you want us to do that outreach for you? Hey, customer ABC, you may be on a subscription, but you’re paying, you know, but we’re invoicing you monthly. Here’s the 3% discount if you just provide us a card and we put that on file, and then we move you to a card on file relationship.

Jacob Olins: And there’s like other benefits that we try to highlight for our customers that we’re just aware of because of our position in the industry at large. So like, there’s a lot of M&A happening in a lot of the industries that,  that we power and, , there’s a lot of, , private equity companies that are interested in acquiring a lot of these services businesses, and that’s like an exit outcome or possibility for a lot of these business owners that like, never were building their business with that in mind. But there’s simple things that these investors, you know, want to see. They want your customer base to be on subscription. That’s equivalent to a valuation multiple. A customer with 80% subscriptions versus 20% is worth so much more. They want those subscriptions to be securitized with a payment instrument on file. And so being able to make that clear, like, hey, we’re recommending you to do this. And by the way, the reason that you’re doing this is not just to, you know, like we believe that that’s going to make you more money and make your business easier to operate. But we can also kind of prove to you that, like, your business is going to be worth more, should you ever be interested in an exit?

Kevin Rosenquist: Yeah, it’s a good point. Most people don’t. A lot of that kind of industry. I bet people don’t necessarily think about that exit part.

Jacob Olins: I think it’s yeah, it’s become there’s been a lot more like the media about it. In the past couple of years, it started to sort of permeate as like an aha moment, I think, for a lot of these folks, but totally like, you know, it’s not the reason that these people started their businesses. , in the vast majority of cases.

Kevin Rosenquist: Yeah. You’re not they’re not a, they’re not a blockchain startup that’s hoping to sell to some big company, you know, sell to Coinbase. They’re a mom and pop playing operation that just wants to, you know, make a living and fix people’s pipes.

Jacob Olins: Keep a couple people employed. Yeah, yeah.

Kevin Rosenquist: Do a couple people employed. Yeah yeah yeah yeah. You know things are changing rapidly obviously. You know, as far as the fintech space, what you were just talking about what you guys are doing and all that. What do you see as big innovations coming for field service businesses when it comes to financial technology.

Jacob Olins: Yeah. Yeah I think financing is a big piece. So , in our industry, in the field services industries that, you know, that we’re  a leader in,  it’s typically like 20 or 30% of our customers’ jobs are like larger ticket kind of services. And so, you know, it was a good example of something like tree trimming, right. If you’re in a lawn care landscaping business. Right. If you’re just doing a regular lawn care mowing service, that’s just a standard kind of subscription service nobody needs. Well, most of the time people aren’t meaning to finance that, right? You don’t finance your gym membership or your Netflix subscription, but, you know, say there was a storm,  a big wind blew and now, you know, the tree that was used to hang over your backyard seems precarious. And it’s gonna potentially fall in your house like that. Could be a big ticket item.

Kevin Rosenquist: Is not cheap.

Jacob Olin: Yeah, that’s not cheap. Yeah. And that’s really dangerous. But, like, do you have 5000, $10,000 cash to take care of that? You know, even if you do like, do you want that to have that much impact on your cash as a homeowner? , yeah. Usually the answer is no.  and so just making that kind of thing more affordable, providing financing plans for those kinds of large ticket services. That’s something that that we’re really focused on scaling out to all our customers and what our customers get out of that also is like they get to sell a lot more services, because in a lot of cases that even if that service is critical, it’s not getting taken care of because it’s unaffordable. , which only makes it worse. Right. Like then the tree falls on the house and the financial obligation is a lot worse.

Kevin Rosenquist: Yeah. The worst case scenario is that a tree falls in your house. Yeah. Yeah. You know, a lot of small businesses, you know, are trying to keep up with the bigger companies. You know, there’s for every, you know, small time player that you have around in my area. Like there’s a big, huge company with multiple people and multiple employees and all that stuff, maybe even a national brand. Do you feel that fintech is, can and does and will help those smaller players, you know, help, help them be a part of it, help level the playing field a little bit more.

Jacob Olins: Oh for sure. I mean, 100% I think it’s like a very big, you know, gap shrinking technology there. You know, like my influence for a lot of the fintech solutions that I try to bring to market is like, hey, what are the largest, most established companies in the world doing? Like they’ve probably figured out at some level, every sort of, you know, way to finance things in clever ways. , and I spent a lot of my career at Citibank and JP Morgan, like working with really large institutional clients, and there were a whole bunch of services that were reserved specifically for the largest companies because, like all that implementation work and onboarding and context getting that, you know, we were talking about a few minutes ago is like really laborious. And so a really large financial institution is only going to spend that kind of investment if they’re going to get a really big outcome. But when we could do that at scale and we can do that, like using the data that is just kind of exhaust from the systems as a result of the businesses working day in and day out. Then we can go and deploy that experience, like to everybody who’s using our system in the same way. That means that we can really remove the barriers to entry to a lot of these solutions that conserve financing. One is a great example, right? Small businesses aren’t going to use their own balance sheet. They’re not going to get, you know, a line of credit from a bank to go do that kind of financing. But what we can bring to life through, you know, our systems, our integrations, , and partnering with, you know, great partners who, who see the same thing that we do. Right. They see a whole bunch of similar looking businesses with similar risk profiles, and therefore a really exciting opportunity.

Kevin Rosenquist: For any business owners, listening to small business owners, what do you see is like maybe the most, if you had to pick one practical change that they could make to optimize their payments, their cash flow, to optimize their financials? What would that one change be in your mind?

Jacob Olins: I guess I paused, because, you know, it’s like,  what?

Kevin Rosenquist: What are they, one I know.

Jacob Olins: Yeah, yeah. So it’s always hard to pick one. I feel like the easy response is like, you know, lean into digital payment acceptance, lean into, you know, I think that like the nexus of that is not like lean into digital payment acceptance and card acceptance. It’s like learning how your customers want to pay? , you know, what is the if you’re if you’ve got a desire for your business to like. And I think this is kind of common in like that small business owner who’s owned a business for a long time and maybe sells to a demographic that is of their contemporaries. Like if you want your business to outlast you or pass on to you, you know, to your kids or your next generation, or you know, you want to sell it at some point, like what is the next generation of customers, consumers out there? How do they want to pay? How do they want to do business? You know, they probably want to be texting and they want to be, you know, using their digital wallets. And , so just, you know, lean into that. Pay attention to what the next generation is, and are interested in from a consumer experience perspective. And then, you know what tools are available to you that unlock that.

Kevin Rosenquist: Yeah, I can attest my wife is a realtor and there’s a lot of younger people buying homes now. You know, the ones that can afford it. Anyway, , are buying homes now, and you got to figure that they’re not going to have a checkbook first of all. And they probably don’t carry cash. So, you know, you gotta modernize if you’re going to attract those kind of new homeowners or new new consumers.

Jacob Olins: Sure. Yeah, right. They’re probably looking at things like Redfin or Trulia first and you know. Yeah. You got to get on on their channels.

Kevin Rosenquist: Yeah. Absolutely. All right. Well the company is WorkWave Jacob Olin, thanks so much for being here. I appreciate your time.

Jacob Olins: Thanks for having me, Kevin. It was a great conversation.