Owning the payment stream for contractors
Anthony Mironov, CEO of Wingspan, on building financial services for contractors
Owning the payment stream is what turns Wingspan from a nice contractor app into the system that controls the whole workflow. Once the company sends work approvals and money through Wingspan, the product can bundle W-9 collection, onboarding, background checks, payout timing, tax withholding, bookkeeping, and contractor wallets into one flow. That is why Wingspan sells to companies first, even though the contractor experience is what makes the product sticky.
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The real bottleneck is upstream of the payout. Mid market companies with 50 to 500 plus contractors are often exporting spreadsheets from project systems, uploading them into Bill.com or bank tools, then reconciling everything by hand. Wingspan plugs into the system where work is approved, so payment can be triggered as part of operations instead of as a separate finance chore.
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This is also how contractor payroll becomes a financial services business. Wingspan charges software fees to companies, then monetizes the contractor side through interchange, instant payouts, deposits, international payments, and insurance commissions. In 2025, Wingspan described its mix as roughly 70% software and 30% fintech, which only works if the funds move through its own rails.
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The competitive backdrop is not just ADP and TriNet portals, but every platform trying to capture contractor spend. Gusto, Rippling, Bill.com, Ramp, Deel, and embedded payroll APIs all want this workflow because the payer payee graph creates repeat onboarding, repeat payments, and chances to sell more services. Wingspan’s advantage is a contractor specific product built around many to many relationships, not a W-2 system with contractor forms added on.
The next phase is less about standalone contractor software and more about becoming the contractor layer inside larger HR, payroll, and PEO platforms. As more workforce systems add 1099 support, the winners will be the ones that own the actual movement of money and the contractor profile that sits behind it, because that is what lets them keep adding faster payouts, embedded insurance, compliance automation, and other high margin services over time.