Automating Contractor Experience Wins
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Anthony Mironov, CEO of Wingspan, on why 1099s are eating payroll
you can't fix contractor management without fixing the contractor experience
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The winning contractor platform is the one that makes payday, paperwork, and support feel automatic for the worker, because that is what removes work for the company too.
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A contractor is not just a different tax code attached to an employee record. Contractors juggle multiple clients, invoices, taxes, insurance, and onboarding steps, so software built around one employer and one worker breaks when it tries to manage that many to many reality.
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That is why contractor experience directly shows up as business value. When payments stall, tax forms are missing, or support is slow, companies absorb the damage through delayed work, extra reconciliation, compliance risk, and more admin load. Wingspan now handles first line contractor support and says AI resolves over 54% of those cases instantly.
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The bigger prize is the contractor wallet. Wingspan says software is about 70% of revenue and fintech is 30%, and the category logic is to use payroll as the entry point, then layer faster payouts, insurance, and other services once contractors are already active on the network.
This is heading toward embedded contractor infrastructure inside every major payroll, PEO, and vertical SaaS product. The platforms that win will not be the ones that merely add 1099 forms, they will be the ones that turn fragmented contractor work into one repeatable flow for both payer and payee, then monetize the network on both sides.