Existing investors Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures, and 186 Ventures also participated in the round.

The funding will accelerate the rollout of Wingspan Embed, a new solution that enables HR and HCM platforms to seamlessly integrate contractor management into their systems. With an embeddable, modular API architecture, Wingspan Embed offers contractor onboarding, tax automation, and payments, as well as value-added services like tax withholding, debit cards, instant payouts, and insurance. Partners can integrate via white-labeled solutions, pre-built UI components, or native APIs – transforming HR platforms into centralized hubs for flexible workforce management.

“Wingspan Embed fundamentally changes what HR platforms can offer their customers,” said Anthony Mironov, Co-founder and CEO of Wingspan. “Instead of juggling multiple systems, businesses can now manage their entire contingent workforce where they already operate. This funding will accelerate our ability to help HR platforms unlock new revenue, reduce churn, and meet the demands of the evolving contractor economy.”

Founded less than three years ago, Wingspan has rapidly scaled its platform, growing its customer base by 200%, increasing average contract value (ACV) fivefold, and supporting 12 times more contractors while processing over $3 billion in payments. The company serves industries ranging from healthcare and insurance to staffing and gig work, with clients including Omni, CRU Group, and Teladoc Health.

Teladoc Health uses Wingspan to manage payments for its 10,000 healthcare providers. “Working with Wingspan has completely transformed the way Teladoc manages 1099 provider payroll,” said Tricia McGimpsey, VP of Payroll at Teladoc. “It’s an incredibly seamless process now.”

The rise of flexible work has reshaped the labor market. According to MBO Partners, 40% of U.S. workers performed contract work in the past year, with $1.4 trillion in contractor payments annually – around 4% of GDP. By 2027, half of U.S. workers are expected to earn income from contracting.

Wingspan’s contractor-first approach – designed to solve challenges around income, benefits, and taxes – has positioned it as a leader in addressing this shift. “From day one, we knew the real problem existed at the intersection of company and contractor,” said Mironov. “We built for freelancers first and used those insights to create the platform businesses truly need.”

The Series B funding will support Wingspan’s expansion into key verticals like healthcare, insurance, and professional services, while continuing to scale its AI-powered compliance and payment automation tools.

“Wingspan is a scalable, intuitive product solving a critical market need, led by a visionary founding team,” said Priya Saiprasad, General Partner at Touring Capital. “Their extraordinary growth and adoption by major HR platforms made us confident in leading this round.”

David Ulevitch, General Partner at Andreessen Horowitz, added: “Wingspan cracked the code on making flexible work work – for platforms and businesses. Every platform will need a contractor stack – the smart ones will embed Wingspan.”