The following interview is a conversation we had with Anthony Mironov, CEO and Co-Founder of Wingspan, on our podcast Category Visionaries. You can view the full episode here: $30 Million Raised to Power the Contractor Experience of the Future

Brett
Hey founders, and thanks for listening to another episode of Category Visionaries. Today we’re speaking with Anthony Mironov, CEO and co-founder of Wingspan, a payroll platform, purpose built or contingent work that’s raised 30 million in funding. Anthony, thanks so much for joining me today. 

Anthony Mironov
Thank you for having me. 

Brett 

Not a problem. Let’s go ahead and just kick off with a quick summary of who you are and a bit more about your background. 

Anthony Mironov
Great. I’m CEO and co-founder of Wingspan, the first payroll platform purpose built for continued work. We’re a fast growing, interesting backed startup that helps companies who rely on 1099 contractors and container workers, build clients onboard, and pay workers and stay compliant. When we founded Wingspan about four years ago, the tension between the promise of flexible work and its compromises was really clear. A lot has changed since then, really the system of record for freelance work hasn’t before Wingspan, I spent most of my early career in private equity. I evaluated over 30 investment opportunities in the peo space due to small business payroll and benefits, which ultimately culminated in a successful sale to Paychex, which is a publicly traded payroll platform. I learned about payroll and how incredibly important somebody’s paycheck is to the fabric of our society. 

Anthony Mironov
And that in addition to spending a number of years as an independent consultant, where I experience firsthand the pains and frustrations of which tens of millions of Americans face led to me starting wasted. 

Brett
I see that you’re backed not just by a 16 z, but also founders of Warby, Parker, Harry’s all birds. What do you think these investors see in you and see in the company? 

Anthony Mironov
Trey were very fortunate to have an amazing partners on our cap table. In addition to that, we have long journey Ventures, Ludlow Ventures, some of the best seed stage investors in New York and San Francisco. Everybody has been really excited about the long term vision of the company. There are more freelancers today than there were yesterday. People talk about the future work today one out of three people in America are feeling to some extent that’s supposed to be north of 50% of population in the next five to ten years. But really nothing has been designed to service this new type of work. And there’s an opportunity to build kind of a transformational platform to remove all of the administrative complexities from a really fragmented ecosystem. 

Brett
And today I feel like it’s pretty. 

Brett
Obvious that the world is moving towards this model and there’s going to be a lot more freelancers. Take me back to 2019. Was it as obvious back then? 

Anthony Mironov
It was obvious for me because I really experienced the problem firsthand. So we started wingspan after experiencing the challenges at the intersection of how companies pay their extended workforces. So previous approaches to managing freelancers really wasteful administrative burden on like contractors and companies, whether it was managing episodic payments or accessing benefits and wrangling 1099 issues, but our world was still operating around a bi weekly paycheck. So I remember as a freelancer myself, chasing a client to pay me, or aggregating piecing together various insurance carriers like Oscar and Guardian, or locking myself in a room to reconcile my life to tax season, I was like, oh my God, this is crazy. There’s 60 million individuals that are struggling with this. 

Anthony Mironov
But as COVID really accelerated this way of working because people realized that they didn’t need to necessarily go to an office and have that similar support system. So there’s actually some really amazing stats of new business applications that are not intended to take people. You can clearly see that theres a gap, which is really exciting because people realize that they can start a business and get the support and the benefits that they are used to. 

Brett
Preston, did you know from day one that it was going to be a b, two b play? Or did part of you think that it could be a B2C play? 

Anthony Mironov
Its a great question. The long term vision has always been to like, how do we become this, the system of record for this massively fragmented ecosystem? We have to own the payment stream and the identity data because in a traditional world everything is kind of handled through the w two, both for companies and for individuals. That’s a really hard to do out of the gate. So we can distribute through businesses and acquire a lot millions of contractors. But let’s start with the contractor experience because that was the biggest gap in the marketplace. Contractors really wanted an all in one experience to manage their life. It started with, I remember three hour ethnographies really learning about the freelancer journey. And the pattern we saw was that folks were effectively getting a PhD in reverse engineering. 

Anthony Mironov
A paycheck and point solution was really addressing the problem at its root. We started with the direct consumer model. We learned a lot. We still have lots of our members from our early days that are still on the platform, and they love it. We learned it was really difficult to scale that business, both from customer acquisition cost and activation. But the platform that we built evolved over time. So during COVID we saw lots of freelancers were working together in like effectively many agencies. And so we built split payments so one invoice could be distributed across a network of freelancers working together. And that led to the technology being able to service really large corporations. 

Anthony Mironov
So we got our first B2B customer, I think it was in the summer of 2022, and we realized that model was a lot more repeatable, especially for a venture backed business. 

Brett
What was it like pivoting the company to prioritize and focus on B2B? I thought that may have been earlier in the journey, but that wasn’t that long ago. So im sure that there was a lot of lag there and theres a lot that had to be changed as. 

Anthony Mironov
You made that shift. 

Brett
What was that like and what did you learn from making that change? 

Anthony Mironov
First of all, we didn’t make the change fast enough. Looking back at it, I probably would have changed the focus a little bit earlier. We always debate internally whether it was a pivot or the platform is 100% the same and at its core, solving the same problem using the same technology. But our go to market had to change drastically. And I didn’t really understand how much of an organizational change that is going from, you know, a self serve signup process online to, you know, learning how to do B2B sales. So I had to teach myself how to do that. Our early team had to basically turn customer discovery conversations to sales conversations and eventually built a sales team, kind of an initial unit of revenue production. 

Anthony Mironov
We had one SDR, a couple, an account manager, and were able to prove that we could build a unit of revenue production to replicate an advance of our series. 

Brett
A lot of changes there, but what would you say was like the most painful change of all? 

Anthony Mironov
I think the pivots are really hard, especially between your seed round and your series A, because you basically have to prove that the business works and it’s fundable very quickly. So going into 2023 was a challenging fundraising environment, and we had to make sure that we had enough cash to prove that the business worked. So it was challenging to kind of like re architect how we charged with types of customers we went after. But at the end of the day, it made a much more resilient and efficient business because it forced us to be much more thoughtful with our resources. 

Brett
This show is brought to you by Front Lines Media podcast production studio that helps B2B founders launch, manage, and grow their own podcast. Now, if you’re a founder, you may be thinking, I don’t have time to host a podcast. I’ve got a company to build. Well, that’s exactly what we built our service to do. You show up and host, and we handle literally everything else. To set up a call to discuss launching your own podcast, visit Frontlines.io slash podcast. Now back today’s episode. 

Brett
Talk to us about the messaging and the positioning changes that you had to make. What was that like? What were those workshops like, and what were those conversations like until you really got the positioning and messaging to a point that it’s at? 

Anthony Mironov
This is part of the company that we didn’t invest in as much as we should have in the early days. We were really focused on building the technology to make this work. So payroll is mission critical. You can’t mess up by an hour or a penny because it’s the most important thing in somebody’s the end user’s experience and obfuscated payments, infrastructure and tax engine and benefits. A really beautiful operating system. The orchestration layer for all of this stuff that is really difficult for millions of companies and millions of individuals to do. But at the end of the day, customers don’t really care about that. And so it was, we had to learn and see what types of customers were best positioned for and really think about starting with positioning. 

Anthony Mironov
So went through, like, a very deep positioning and segmentation and messaging exercise of what are the competitive alternatives and like, where do we fit into somebody’s life and in their context, and how do you really deep and very specific product marketing. So we’re dealing with some of the largest companies in the world, right? There’s ADP, there’s paychecks, there’s conglomerates that have been around for whether it’s 75 years or 25 years, and they’re trusted businesses. There’s also accounts payable solutions that are bill.com or those traditional it players. But we’re solving a very different problem that’s really service traditional w two payroll systems or accounts payable systems. So we had to figure out how do we compare what somebody is really against them because they’re not purpose built for the specific industry or this specific use case. 

Brett
Can you talk us through what purpose built means for you? Like, what is it about how you’ve approached building that would make it difficult for, let’s say like an ADP to say, okay, now we’re going to service contractor as well. They just throw it on as side product clay. 

Anthony Mironov
So taking a step back, we service companies that are built on attention work. So parts of the business, these aren’t back office functions. And that’s critical because there’s lots of industries that are traditionally designed. So if you think about it like insurance or real estate or professional services, mental health therapy platforms, they have a pool of contractors that sell time, so they have to bill their clients and then they have to pay all of their workers and there’s a, and put them to work and check their eligibility requirements, do a background check, e signatures, and upload a bunch of docs. And that’s just to get started. And then you have to input the amount of time that they work into the system and do automated accounts receivable and accounts payable. 

Anthony Mironov
And there’s a big tax process, and you have to kind of wrap all of that in a bow and send it out to the ERP accounting systems. In addition to that, these workers are really core to the business. So recruiting and retaining that talent is fundamental to these industries. So folks want financial and health benefits just like w two employees. And we saw this over and over. Businesses that have revenue generating contingent workers have all of these problems. And the adps of the world were never really designed for this because the w two role is really, you set it and forget it. There isn’t the same lifecycle management aspect of it. And thats what makes our solution really purpose to services market. 

Brett
Trey, when it comes to your market category, how do you think about the market category that you’re in and the category that you’re going to be in two or three or four years from today? 

Anthony Mironov
We think about market categories a lot because of the context setting and going back to the positioning thats super important. And we’ve debated whether its, you know, category expansion versus category creation. So categories potentially better payments. Like people are searching for payments because they have a payment problem. But what we learned was some of those services are really a lot of these in terms of like, they’re not really about the entire workflow necessary to manage this business. They’re really kind of like, at the last mile, there’s hundreds of ways, there are really thousands of ways to pay an individual, but all of the pain kind of comes before that. 

Anthony Mironov
So we decided to really hone in on this lifecycle management of contingent work as the category that we are developed over time, which is a massive opportunity because when you think about platforms out there’s shopify that’s really built for e commerce. There’s square. That’s if you’re running a POS business or a retail business of square. Both of those businesses have created really beautiful ecosystems for multiple stakeholders across their merchants and the recipients of the cash app experience and so forth. And we see a really big opportunity for contingent work, which is effectively professional services. 

Brett
I think there’s obviously a lot of noise in this space. There’s some companies that probably aren’t attacking it in the same way, but if you go to their website, it would be a lot of similar language that’s used. What are you doing to stand out from all of that competition and rise above all that noise and capture the attention and demand that’s out there? 

Anthony Mironov
We’re early in building out our go to market engine. We were pretty quiet for a couple of years, just really heads down building the technology to make this work. And what’s been resonating recently is elevating our customer stories of customer success. So we’re really high NP’s score, best in class in that dollar retention and our customers really love our product. And over and over I hear how they’ve been searching for something like wingspan for 2025 years and they’re really proud of sharing their story. So that’s what we’re doubling down on right now, is play where we win. 

Brett
How do you get customers to be okay with that? Obviously your space is a little bit different. I work with a lot of companies in like, cybersecurity and it’s like, yeah, good luck getting a cybersecurity customer to do a case study or do a customer success story for you. What’s in it for them? And how do you get people to be okay with sharing their story and talk about how they’re using your platform? 

Anthony Mironov
Look, earlier in our journey, the companies that were signing up were buying into our long term vision because we saw the world differently and they bought into that mission. They’re extremely. Because we are saving them hundreds of thousands of dollars and transforming their business and we’re providing a much better experience for their workforce, which is really a high priority. So I think there’s an interesting dynamic with us because the companies are using wingspan as a recruiting and retention mechanism and when we initiate verticals, we oftentimes hear some workers won’t work with a company if they’re not on wingspan. So I think they’re happy to share their success stories because at the end of the day, they’re making their workers more successful. 

Brett
As I mentioned there in the intro. 

Brett
You’Ve raised over 30 million to date. What have you learned about fundraising throughout this journey? 

Anthony Mironov
I’ve learned a lot. I think the number one lesson is that fundraising is the sales process. Similar to learning how to do B2B sales. After really focusing on the product experience and the technology, I think learning how to run an efficient fundraising process is a muscle that everyone can develop and just approaching it as a sales process makes it a lot more manageable. 

Brett
Final question for you, let’s zoom out three to five years into the future. What’s the big picture vision here? 

Anthony Mironov
I’m confident we could be the largest financial services company in the world and definitely in the US. So, you know, there’s Shopify that’s really designed for e-commerce businesses and they built a really beautiful ecosystem for developers to build on top of their APIs. Similar to that for folks that are selling their services in person. Square has built really beautiful ecosystems for merchants and for individuals. We think that we could fill that need for this massively growing workforce for professional services and really a unified platform built on a really unique contractor graph that removes all of the administrative complexity of working for yourself. 

Brett
Amazing. I love the vision and I really love this conversation. We are up on time, so we’ll have to wrap here before we do, if there’s any founders that are listening in that want to follow along with your journey, where should they go? 

Anthony Mironov
You can learn about us at our website, www.Wingspan.app so Wingspan.app. Awesome. 

Brett
Anthony, thanks so much for taking the time. 

Anthony Mironov
Thanks so much. 

Brett
This episode of Category Visionaries is brought to you by Front Lines Media, Silicon Valley’s leading podcast production studio. If you’re a B2B founder looking for help launching and growing your own podcast, visit Frontlines.io podcast. And for the latest episode, search for Category Visionaries on your podcast platform of choice. Thanks for listening and we’ll catch you. 

Brett
On the next episode.