The Future of Work with Desmon Lewis of Gig Wage | Soar Payments LLC

The Future of Work with Desmon Lewis of Gig Wage

Payroll has historically been focused on the W2 employee. In the swift and ever evolving gig economy there has been a major shift toward 1099 contract work. In this episode we sat down with Desmon Lewis, Senior Sales Executive of Gig Wage, to talk about how the workplace is changing and how innovation in payment systems is following suit.

Payments & Fintech Insights In This Episode

  • How saying “yes” in uncomfortable spaces can shape a tech career.
  • The importance of economic empowerment in a growing gig economy.
  • The essential nature of seamless, centralized, digitalized process for receiving payments.
  • How a SaaS companies are paving way to improve the gig economy.
  • And so much more!

Episode Transcript

Heather: Hey, everyone, welcome to PayPod. I’m your host, Heather Bodie, and today, we’re gonna be talking about managing all things related to the 1099 experience. Joining me today is Desmon Lewis. He is a Senior Sales Executive at Gig Wage. Desmon, welcome to the show.

Desmon: Thank you, Heather, for having me. Glad to be here.

Heather: So, before we actually get into the nitty-gritty details about Gig Wage, I wanna start by exploring your personal career path into FinTech. Tell me a little bit about yourself. How did you get into the industry?

Desmon: So, I had a little bit of a different path in the industry. On the personal side of my life, I describe myself as a product of philanthropy. I was born and raised in the South Bronx, which means a lot of things to a lot of people, but what it meant for me was economic opportunities growing up were not that prevalent. You know, I grew up in a family of nonprofit leaders. I grew up in the nonprofit sector, affordable housing, you know, food insecure. I grew up in a digital desert, and I was a first-generation everything, high school student, college graduate, etc.

And I kind of knew early on that financial empowerment or economic empowerment was critical to a family’s well-being, a personal well-being for any individual. And so I actually started a foundation in the Bronx, which we can talk about later, which focuses a lot on that. But in my professional life and how I got to where I am today, I really describe myself as a technologist with a banking license.

So, I started my career in FinTech. It wasn’t called FinTech back then. It was called the Transaction Services Business, which is basically around how do you move money? How do you make payments around the world? And I wanted to go into banking because I knew that economic empowerment started with finance and started with getting money into people’s hands. And so where I started my career was at the beginning of the FinTech revolution, you know. I joined the financial services industry when payments weren’t really a sexy place to be if I can use that phrase.

Heather: Yeah, absolutely.

Desmon: And now it’s one of the sexiest industries to be in with all of the fast-growing startup companies. And so my personal life kind of influenced my professional life of wanting to be at the core of all of that, and I really was kind of at the right place at the right time. That evolved into me learning about the payments business being at the forefront of innovation in the industry. I was there when open banking was created. I was there when mobile payments started coming to the forefront, card solutions at the beginning of some of that revolution and innovation.

So, where I currently am at Gig Wage really allows me to continue to be at the innovation end of the tip of the spear within the FinTech industry. That’s my personal and professional career trajectory thus far. And, of course, I can go into any more detail as you see fit.

Heather: I’m the Executive Artistic Director of a nonprofit here in the city of Chicago. So, of course, my nonprofit heart wants to follow that path. But for the moment, we’re gonna stay in the land of FinTech, but I promise to come back around to that. I heard you say the phrase “I was in the right place at the right time.” Can you talk a little bit about…? I don’t know, I just like for you to expand on that.

Desmon: Sure.

Heather: Folks ask me about my own career path often, and I find myself being like, “I don’t know, you know. I just, like, followed where my instinct led.” Do you feel like it was true luck when you say “Right place, right time? Or do you feel like this was sort of, like, a convergence of all the preparation, all the things you’d said yes to up to that point?

Desmon: It was definitely both. Everyone in their life, you know, call it luck, call it a blessing, whatever that may be for you. I think you’d make a decision. And then for most people, you know, stars tend to align if that decision is true to sort of your passion, what gets you up every day. And so when I graduated into the banking industry from college, I chose that business and industry I didn’t know the most, right? Or I knew the least, right? Transaction banking at the time in the early 2000s wasn’t a business many people knew about because you didn’t learn about it in business school. You tend to learn about investment banking, or capital market, sales and trading. I really chose to go into a space I didn’t know much about and to get into an uncomfortable situation for myself, and put myself in a situation that challenged myself.

So, whether that was luck or just me wanting to learn something new, I ended up in the payments industry and the transaction banking industry at the start of it, so things like the Single Euro Payments Area. I moved to Europe right as that was being rolled out, SEPA. SEPA led to open banking, right? Which is the revolution of open data and how technology and FinTech companies primarily leverage and work with large financial institutions to innovate. I was there when QR code technologies were starting to be rolled out on mobile phones and mobile payments in Sub-Saharan Africa and some of the emerging markets.

So, just saying yes to different challenging situations or things I didn’t really know that much about I think are the reasons why I ended up in certain places. And yeah, you have to, you know, be at the right place at the right time. A lot of it is around, like, just identifying spaces that you’re not comfortable being in and going into those spaces, and I think 9 out of 10 times you end up in a place that tends to be different, new, you know, beginning, cutting-edge, etc.

Heather: So, take us to Gig Wage. How does it work? Why is it so important? Let’s dig into the details of where you are currently serving in the FinTech world.

Desmon: Sure. So, the gig economy, the 1099 economy is sometimes called a new and innovative space. You can’t see me but I’m using “new and innovative” in that. Payroll has been around for a very long time, right? Payroll has been around for over a century. But from an innovation standpoint, a lot of payroll is focused primarily on the standard worker, the W-2 worker, if you will. And the big opportunity, particularly as COVID has shine a light, but Gig Wage has been focused on this well before COVID is that the flexibility of work, the ability to provide multiple streams of income, the ability to not be tied to a desk, or tied to a particular industry or focus is the most exciting part around the future of work.

And so Gig Wage, we’re a payroll payments and banking technology company that focus exactly on that. We focus entirely and only on the 1099 gig worker. I like to describe for people who don’t know what it means, think of the ADP, where ADP for fast-growing contractors or the gig companies. So, we help modernize, innovate, revolutionize and really retain and grow from a compliance standpoint as well the 1099 worker. So, that’s everything from onboarding compliance, so think of W-9 capture to payments. So, we do on-demand, instant pay, standard payments, and then we do one of the more complex things is the 1099 filing at the other end.

And so we really remove the barrier for companies to pay their contractors, their workforce instantly on-demand whilst also coming back to this economic empowerment message, providing those contract workers the ability to be paid when they want, how they want, and where they… So, that’s really Gig Wage. We’re a SaaS technology company that’s really innovating the gig economy from payroll payments and banking standpoint.

Heather: I’ve spent the last 16 years of my career always collecting some sort of 1099s at the… I’ve always been in this gig economy. And it continues to make me laugh that even after 15,16 years of working that way, for me, with so many of my clients, the system is still the same, and tax time rolls around, and, you know, I’m, like, plying through all the different paperwork to make sure I have everything, and what payment came from where, and when? And am I missing a check? Did it go to the wrong address?

So, this idea of digitizing and modernizing and innovating that workflow, especially as a result of the way the workforce has changed posts. Well, we’re still sort of in the lingering ends of this pandemic. It just feels beyond necessary, you know. We’ve been craving it for so long and now it’s a must.

Desmon: Absolutely. It is with everything we have going on, right? And I’m using that in the generalist of terms. This should be the easiest, right? How you get paid and how you reconcile that payment. Again, as I said earlier, payment has become a sexy industry. We wanna make it easy and less cumbersome, right? So, from that standpoint, yeah, how you get paid, where you get paid, the reconciliation of that, and the IRS compliance piece should all be centralized, digitized, and really easy to manage. And we do all of that via API, which is another way for companies at this tip-of-the-spear innovation standpoint to leverage our technology in the easiest, most seamless way.

Heather: Let’s talk about easy, seamless. I know integrations can be a sticking point when it comes to adopting new software. And I imagine, and I’m making an assumption here, so stop me if I’m off track, but I imagine some of your more recent clients are companies that were more focused on that W-2 employee and are now transitioning to say the workforce is changing to get the talent we want. Now we’re looking at sort of tipping the scales, having more and more people every day who are on that W-9 track.

So, with those kinds of companies, have you had any sticking points around integrations and adopting the new software? Talk to me about what a client can expect from Gig Wage during that early part of the process when they decide to adopt your platform.

Desmon: Sure. So, the other point just to raise as you mentioned sort of companies shifting to 1099 workers, you know, there’s also this IRS change that’s recently happened. So, as a part of some of the infrastructure package the Build Back Better bill that happened last year, the IRS has shifted some of the tax requirements. And so the threshold for filing a 1099 has come down tremendously. It used to be around $20,000. If you got paid $20,000 or more in a single year, you had to file 1099. That’s come down to $600, particularly for marketplaces. So, this is not just an industry shift, it’s a regulatory shift as well.

So, from an integration standpoint, just to answer your question, one of our key differentiators at Gig Wage is that we think like developers. We build fast and we innovate quickly. We’re really a developer-first company. Our CTO is a developer. Many of our product team, we are heavy product-focused developer company. And so that’s probably one of the biggest feedbacks we receive is that we build and innovate and move quickly.

And so from an API standpoint, our APIs are very public, they’re very clean, We are best known for hand holding and really working with our company’s developers to provide what we call a consultative solution design process from the start. We’d like to understand what the existing solution is, map out the existing technology topography, identify any immediate challenges, and then directly build that roadmap using our API documentation. So, it’s very, very quick and seamless.

We recently, as an example, rolled out a very large innovative company. They’re unicorn. They have about 50,000 plus 1099s they need to file. And they’re a huge, huge company, right? In some cases, a little bureaucratic. And we were able to develop an entire API solution for 50,000 plus contractors within 5 weeks. If you’re a developer, that’s a tremendous amount of…

Heather: That’s incredible.

Desmon: Yeah, of effort in a short period of time. So, we really lead with that ability to do that. And for large companies, large enterprise companies, which is what I focus on, to help them build quickly and innovate quickly.

Heather: What about security and privacy? I know our industry has very much a key role to play in protecting both consumers’ and business data. What is Gig Wage’s philosophy when it comes to data security?

Desmon: Yeah, I mean, it’s core to our platform, you know, considering we capture and manage PII, personally identifiable information amongst other critical data that we do. You know, securitizing data is paramount to our business. Our primary objective, generally, as we’re designing these solutions is to ensure that our entire platform is really safeguarded and that our client data during the preparation, the transmission, or processing of that data, all of that is safeguarded.

So, we utilize leading technology, leading-edge security technology to protect and secure our clients. You know, payment transactions, PII information, this is a question we quite often get. So, we also follow stringent industry regulations as well, right? And how we operate as a business and how we manage data. So, whether that’s SOC compliance, or otherwise, we’re making sure that all of that is paramount because of the type of data we collect.

Heather: Talk to me a little bit about an ideal client. Is Gig Wage the right fit for a business of any size, or is there a particular sweet spot?

Desmon: So, we, as a company, cover the entirety of the gig economy. So, every industry, we joke that by the end of the year, we pay Santa Clauses a lot because those are 1099 workers. And then some of our largest clients are marketplaces, if you think, whether peer-to-peer marketplaces or ride-sharing companies. So, we do cover SMBs, so small companies. Think of companies paying 5, 10, 20 contractors, up to companies paying tens of thousands of contractors a month. And so…

Heather: Like you said that unicorn that’s got the 50,000 1099 contracts. That’s huge.

Desmon: Absolutely. And our technology caters to both, right? So, we have… SMBs will, you know, be primarily a part of our web application experience, which we have for our smaller clients, and then we have a full end-to-end API connectivity for our larger enterprise. And so the gig economy is a very diverse place with companies, and so our technology caters to that diversity.

Heather: One of my best friends from high school, her parents are professional Santa and Mrs. Claus. And I am just floored by how busy they are from October all the way into January. It is a big Santa Claus season.

Desmon: It’s a huge business.

Heather: It’s a huge business. They go to conventions. It’s wild.

Desmon: Yeah. It is.

Heather: Oh, my gosh.

Desmon: It’s our most entertaining part of the gig economy. Absolutely.

Heather: So, do you get to hear…? This is just a curiosity of mine. Do you get to hear from the folks who benefit from the seamless nature of, you know, the actual gig workers themselves? Or is the majority of your direct feedback coming from the companies that are utilizing your platform? I just am excited about the idea that you sometimes could potentially talk to the folks who are in the boat I was talking about earlier lost in payments and tax documents.

Desmon: That’s a great question. So, in addition to being a B2B company, we’re also a B2C company, and so the contractors, the 1099 recipients that get paid also engage with our customer success team. And so we do quite often get to…and we pretty much on a daily basis will get a message from a contractor saying, “This is the fastest I’ve ever been paid,” or, “This process is very easy.” Last year, we had our 1099 season. People were saying, “I’ve never had my 1099s digitally given to me like this.”

Heather: Yes.

Desmon: You know, it builds customer loyalty for our B2B clients. Every day, we’re just really, again, privileged to be in a position to see exactly what our technology does to improve the lives of contractors. So, yes. And we also, through our growth team, quite often will hold forums. We will just take feedback from our B2B clients, but also our contractors to say, “What else are you seeing out there? What are things that we can be doing to improve your experience?” And I quite often join those calls just to hear how our solutions are helping improve because then it helps us provide a better overall technology to our B2B clients as well.

Heather: I love that. So, when you’re sitting around…and you’d mentioned actually before we started our conversation in a recorded fashion. I had asked if all of the folks in your company are in one location, and you had mentioned they’re sort of spread all over the country. So, I was gonna say when you sit around a table, but maybe more so when you sit on a digital or virtual meeting and you’re working on strategy, what does dreaming and scheming look like for Gig Wage? Where, as a company, do you see the functionality of the gig economy progressing to, let’s say, far down the road, like 10 years from now?

Desmon: Yeah, because we’re a company of technologists, we’re always innovating and thinking about the next evolution of this industry. And we want to become the backbone, the payment infrastructure, the financial infrastructure for the gig economy. And what we’re seeing in 10 years is that the gig economy becomes mainstream. Everyone always talks about how it’s gonna be the primary workforce in the U.S. and the world, and it certainly will be. But what I mean is students or young people let’s say between the ages of 18 to 30, I think they’re gonna start their career as a gig worker. So, no longer you have this pressure or this sort of let’s just say expectation that everyone starts their job as a W-2 worker.

I think people are gonna start off experimenting in industries and figuring out where they fit and what their interests are and what their passions are. And that’s probably gonna start in the gig economy. And then they’ll probably work into becoming maybe a W-2 worker and keep some of their gig work on the side, right? I think we’re seeing a lot of the trend is that a lot of W-2 workers are taking on gig work. And that’s probably because of benefits if you really look into the details, healthcare. All the various things you get as a W-2 worker you don’t get holistically as a 1099 worker. But again, that’s also changing.

So, a lot of companies that are approaching us, some of them who are existing clients are revolutionizing that piece and trying to bring all of the benefits that W-2 workers get to the gig economy. I think as soon as you start to get that at scale, then the pendulum really shifts, and it moves away from just being a side hustle industry to being a real leading income-generating industry. So, that’s what we’re seeing is, like, gig economy in the next 10 years will become mainstream and a first choice for a lot of people, I would think.

Heather: I’m so glad you said that. As I asked the question, I was like, “I wonder if he’s gonna touch on benefits,” right? Because that’s really…I mean, especially I have so many conversations with folks who are leading tech companies that are the big players. And I feel like tech is the forefront for this where the benefits are beyond those traditional health insurance, 401(k), those sorts of things. But it’s this, like, big, shiny workplace, the unlimited vacation, right, all these other elements around. I feel like tech has always been the innovator in employee benefits as well. And I have just ache for somebody to disrupt this space of what it would look like to be able to provide benefits packages for gig workers because I think you’re absolutely right. We’re gonna see the workforce shift in that direction. And that, again, will be a necessity that so many of us have been craving for years and years and years.

Desmon: Without a doubt. We have a couple of companies who’ve used our payment technology that are exactly in that space, so providing healthcare, providing insurance services, providing… And insurance not just as it relates to the typical dental, vision, etc., all the other…depending on the industry, car insurance, and other types of related insurance. So, yeah, it’s already here. It just hasn’t gone mainstream. And I think we’ve also been approached by large insurance carriers to say, “Hey, how can we work with you to figure out what do gig workers need, and build a product in partnership with you?”

And then the other interesting bit is also the rating agencies. So, you think about one of the biggest hindrance for gig workers as well is the income, right? Generating that income profile through rating agencies to be able to get car loans, mortgages. That’s also shifting tremendously. So, I think we’ll see definitely within the next 10 years the rating agencies start to look strongly at this space. And some have already started talking to us about how we can build a profile for a gig worker to, again, get some of the same benefits a W-2 worker receives.

Heather: So, what’s next for Gig Wage? Are there any immediate updates or anything you can let us in on that’s happening in the near future?

Desmon: Yeah, we have so many exciting things coming. From our perspective, the future of the gig economy is evolving so quickly and changes very rapidly that we have to maintain and stay at the forefront of that. And so the good thing about Gig Wage and our platform is that we’ve built a real sort of modern, flexible financial technology. And so our infrastructure makes it easy for our solution to rapidly evolve and take a veil of what’s happening in the space. And so we just rolled out FasterPay, which is on-demand pay. We’ve had kind of faster payments, but we’ve sort of innovated and revolutionized that based on some of our clients’ needs, and we’ve had a tremendous amount of adoption rate there.

You know, I think the need for on-demand payments and sort of credit-based solutions, that’s the other piece that we’re gonna roll out, has increased tremendously, particularly since COVID. So, we’re having and developing solutions to help satisfy that need as well. And then there’s a whole host of other things. I’ll just say watch this space, that we’re gonna be announcing in the next 6 to 12 months. That, again, is really focused on where the gig economy is heading and where a lot of our contractors as well as our B2B clients are needing services for.

Heather: To wrap us up, I wanna return back to something you mentioned right at the top of our conversation as promised. I’d like to talk a little bit about the nonprofit that you mentioned that you started in the Bronx. And if you can, can you tie in the importance of the gig economy with that financial literacy component? I’m not sure if they do. Sort of, I imagine that they overlap.

Desmon: Yeah, they do.

Heather: But I’d like to hear a little bit about that organization and how you see the gig economy sort of bolstering the future for the folks who benefit from that org.

Desmon: Sure. So, my brother, Derek, and I, we co-founded the first community foundation in the Bronx which is called The Bronx Community Foundation, the website, And really, it’s focused on bringing economic empowerment to what still remains as one of the largest economically impoverished places in the country. So, the Bronx is a place of great opportunity. It’s great diversity, a lot of great things that the Bronx has given to the world. But one of the things that we are focused on is bringing financial security and building generational wealth and economic empowerment into the Bronx.

And one of the things and the reasons why I decided to come to Gig Wage is because core to our CEO’s mission and vision is economic empowerment and financial empowerment. And one of the things that we’re trying to do in Gig Wage both as my professional life but also at my foundation is to bring people into the financial ecosystem. Large banks, large financial services institutions, in general, haven’t catered to the underrepresented, underserved demographic. And one of the things that my foundation as well as Gig Wage does in tandem is we focus on bringing opportunities and financial tools to those who’ve been excluded from that industry for decades.

So, I think there’s a nice tie between nonprofits that do this work and Gig Wage as a company because, at the end of the day, gig workers represent a disproportionately underserved demographic. And being able to provide the tools that we provide at Gig Wage to give payments and provide on-demand economic needs, credit facilities, and just simply having a bank account and an account linked to that payment, which, you know, we’re also considering rolling out in the future is important to bringing people into the financial ecosystem. And that’s one of the goals of Gig Wage, and one of the real empowering messages that we put forward to every one of our clients. And so, yeah, really excited about being able to do that work on the nonprofit side, but also every day coming to Gig Wage with that mission and vision as well.

Heather: Incredible. Desmon, thank you so much for joining us today. If folks wanna get in touch with you or learn more about your company or about your nonprofit, where can they find you?

Desmon: Sure. So, they can find us at where you can reach out to our team to learn more about our company and all the innovative things that we’re doing.

Heather: Beautiful. Thank you. Thank you again for joining us. This is an incredible conversation. I appreciate it.

Desmon: Thank you, Heather. I appreciate your time.

Heather: If you enjoyed this episode and wanna hear more, head on over to to subscribe on your podcast listening platform of choice. That’s

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