Contractor-Native Back Office Platforms
Anthony Mironov, CEO of Wingspan, on the convergence in back-office SaaS
The key point is that Wingspan is not selling to generic freelancers, it is selling into old contractor heavy workflows that already run core operations for insurers, staffing firms, and large brands. In these markets, 1099 is not a temporary loophole or a new gig trend. It is the default labor model, with a big payer, an intermediary, and hundreds or thousands of specialists who need onboarding, checks, payments, and tax handling every time work is assigned.
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The common pattern is structural, not industry specific. Wingspan describes insurance, creative services, healthcare, legal, accounting, and virtual assistant networks as different on the surface but similar underneath, one large payer, one coordinating company, and a large contractor base. That is why a horizontal contractor system can work across them.
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These workers sit awkwardly between employee payroll and vendor payables. Legacy payroll systems were built for W-2 staff. AP tools treat each person like a one off vendor. That leaves teams manually collecting W-9s, running background checks, verifying licenses or insurance, sending payments, and issuing 1099s across finance, HR, and operations.
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This is also why the category matters strategically. Generic payroll platforms work fine with a handful of contractors, but they break at 50 to 100 plus. That gap has pulled in Rippling, Gusto, Deel, PEOs, and embedded partners, all trying to own mixed W-2 and 1099 workflows without letting contractor spend leak into Bill.com or other point tools.
Going forward, the winners will be the systems that become the record layer for repeat contractor work in these long ignored verticals. As more enterprises blend full time staff with large contractor networks, the advantage will shift to platforms that can reuse identity, compliance, and payment data across every new engagement and every new payer.