Free Contractor Software as Payments Funnel
Anthony Mironov, CEO of Wingspan, on building financial services for contractors
Wingspan is using free contractor software as the top of a payments funnel, where the real upside comes after the contractor gets paid. Once money lands in Wingspan, the company can earn on how that money moves and where it sits, through card spend, instant payouts, cross border transfers, deposit balances, and insurance enrollment. That turns a zero price product into a growing transaction and services business.
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The model is already meaningful. In 2025, Wingspan said revenue was roughly 70% software and 30% fintech, with fintech expected to expand as the contractor network scales. That shows the free user side is not a loss leader in theory, it is already a live revenue stream.
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This works because contractor payroll platforms touch both sides of the money flow. They charge companies a platform fee and per contractor fee, then monetize the worker side through instant transfer fees, FX on international payments, deposit interest, and interchange. In mature models, those fintech layers can exceed the software take.
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The strategic prize is the contractor wallet. Wingspan has processed over $3B in payments, and one third of contractors on the platform are paid by multiple payers. That makes Wingspan more than a payroll tool for one company, it becomes the place contractors use across jobs, which raises attach rates for cards, payouts, and insurance.
The next phase is deeper wallet capture through embedded distribution. As Wingspan plugs into HR, HCM, and PEO platforms, more contractors will receive money inside the same rails from day one. That should push more payment volume, more balances, and more financial product attachment onto the platform, making fintech monetization a larger share of revenue over time.