Freelancer Management and Payments Unbundled
Matt Drozdzynski, CEO and co-founder of Plane, on global payroll post-COVID
The strategic opening is that freelancer infrastructure no longer has to be bundled with a talent marketplace. Upwork proved companies will pay for both sourcing and payments in one product, but the next wave is software that only handles onboarding, contracts, tax forms, invoicing, and payouts after a company finds talent on its own. That creates room for multiple winners because the workflow for managing a project based freelancer is different from running payroll for a core long term team member.
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The unbundling is concrete. Instead of paying a marketplace take rate to find a designer or recruiter, a company can source through LinkedIn, referrals, or its own brand, then use contractor software just to send contracts, collect W-9 or W-8 forms, approve invoices, and push payments.
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A separate category is viable because the market is large and structurally different from classic gig platforms. Freelancer earnings were estimated at $1.4T of annual B2B payments, and most nontraditional workers were outside marketplace platforms like Upwork. That leaves a much bigger pool for infrastructure vendors than for labor marketplaces alone.
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The strongest specialists look more like payroll plus fintech than like job boards. Wingspan focuses on companies with hundreds or thousands of contractors, automates onboarding and reporting, and layers in contractor facing tools like tax withholding, bookkeeping, benefits, and faster payouts. That is a very different product shape from an Upwork style marketplace.
The category is heading toward a split market. One set of products will specialize in freelancer first workflows, fast onboarding, repeated invoicing, and contractor wallets. Another will blur contractors and employees inside one payroll system. As more companies source talent directly, the infrastructure layer will keep expanding, and the winners will be the products that make repeat contractor payments feel as simple and reliable as payroll.