Wingspan, a payroll platform built specifically for contractor management, has raised $24 mn in a Series B round led by Touring Capital.
This brings the company’s total funding to $54 mn. Existing investors Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures, and 186 Ventures also joined the round.
The funds will accelerate the rollout of Wingspan Embed—a modular API product that allows HR and HCM platforms to offer contractor onboarding, tax automation, payments, and additional services such as withholding, debit cards, instant payouts, and insurance.
Integration options include white-labeled tools, pre-built UI elements, and direct API access, enabling HR platforms to offer contractor support without building new infrastructure from scratch.
Wingspan Embed gives HR platforms an opportunity to consolidate their contractor operations within their existing systems
Anthony Mironov, CEO and Co-founder
“It reduces the need for third-party tools, increases platform retention, and creates new revenue opportunities,” said Anthony Mironov.
Since its launch less than three years ago, Wingspan has grown its customer base by 200%, increased average contract value fivefold, and now supports 12 times more contractors.
For the first time ever, businesses can now automate the full lifecycle of flexible work including onboarding, invoicing, payments, compliance, and benefits – all in one place.
Wingspan is trusted by hundreds of businesses that rely on a flexible workforce to drive revenue, and we’ve saved them all thousands of dollars and countless headaches.
The platform has processed over $3bn in payments across sectors such as healthcare, insurance, staffing, and gig work. Clients include Omni, CRU Group, and Teladoc Health.
Teladoc manages payments for 10,000 healthcare providers using Wingspan. “It’s a seamless process now,” said Tricia McGimpsey, VP of Payroll at Teladoc.
Contract work now represents a major segment of the U.S. labor market. MBO Partners reports that 40% of U.S. workers earned income through contract work last year, generating $1.4tn—approximately 4% of GDP. By 2027, half the U.S. workforce is projected to participate in contract-based roles.
Wingspan focuses on contractor needs first, solving issues around income, benefits, and tax handling. “We started with freelancers,” said Mironov. “Their pain points shaped what we built for companies.”
The company plans to expand into healthcare, insurance, and professional services while continuing to scale its AI-driven tools for compliance and payments.
Wingspan’s traction and customer adoption speak for themselves. It’s a well-designed product solving a real operational challenge.
Priya Saiprasad, General Partner at Touring Capital
David Ulevitch, General Partner at Andreessen Horowitz, added: “Any platform dealing with flexible work will need a contractor stack. Wingspan delivers that stack, already tested and ready to deploy.”
