Wingspan, a modern payroll platform designed for contractor management, has raised $24 million in Series B funding led by Touring Capital, bringing its total capital raised to $54 million. Key investors, including Andreessen Horowitz and Long Journey Ventures, also participated.
Wingspan’s mission is to simplify contract work. In under three years, the company has increased its customer base by 200%, boosted average annual contract value by five times, supported twelve times more contractors, and processed over $3 billion in payments. With around 40% of U.S. workers engaging in contract work, businesses are increasingly relying on this labor model.
Wingspan serves various contractors, including gig workers and insurance adjusters. It is utilized by Teladoc Health, which saves an average of 28 hours per month on payment processing for its 10,000 healthcare providers.
Additionally, Wingspan is introducing Wingspan Embed, a solution that transforms how HR platforms manage contractors. It features contractor onboarding, tax automation, payments, and value-added financial services, such as instant payouts and insurance. The modular API allows easy integration into any HR platform.
The funding will accelerate Wingspan Embed’s adoption and expand its reach in key sectors like healthcare and staffing. Wingspan plans to enhance its team and develop AI-powered products to automate contractor compliance and streamline payments, addressing the needs of flexible workforces.
KEY QUOTES:
“From day one, we knew the real problem existed at the intersection of company and contractor. We strategically started by building for freelancers—learning their pain points around income, benefits, and taxes—then leveraged those insights to create the comprehensive platform that businesses desperately need. We’ve now completed the circle with the only solution that truly works for both sides. The workforce composition is changing, and platforms that plan for this shift now will be well-positioned for the long haul.”
“Wingspan Embed fundamentally changes what HR platforms can offer their customers. Instead of forcing businesses to juggle multiple systems, they can now manage their entire contingent workforce where they already work. This funding accelerates our ability to help HR platforms unlock new revenue streams, reduce customer churn, and handle compliance complexities that have held them back from serving the contractor economy.”
Anthony Mironov, Co-founder and CEO of Wingspan
“Working with Wingspan has completely transformed the way Teladoc manages 1099 Provider Payroll. It’s an incredibly seamless process now.”
Tricia McGimpsey, VP, Payroll at Teladoc Health
“Wingspan is a scalable, intuitive product solving a critical market need, led by a visionary founding team. The company’s extraordinary growth and rapid adoption by prominent HR platforms gave us the conviction to lead this funding round. We are proud to support Anthony, Greg, and the entire Wingspan team as they continue to modernize the infrastructure for contract work.”
Priya Saiprasad, General Partner at Touring Capital
“Wingspan cracked the code on making flexible work work—for platforms and the businesses they serve. Every platform will need a contractor stack—the smart ones will embed Wingspan.”
David Ulevitch, General Partner at Andreessen Horowitz
