Wingspan raises $24m for embedded contractor management in HR platforms

Finextra

29-07-2025

Wingspan, the first modern payroll platform purpose-built for contractor management, announced that it has raised $24 million in Series B funding led by Touring Capital, bringing its total capital raised to $54 million.
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Existing investors Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures, and 186 Ventures also participated.
Wingspan is on a mission to make contract work effortless for everyone. In less than three years, the company expanded its customer base by 200%, increased average ACV by 5x, supported 12x more contractors, and processed $3B+ in payments. Wingspan's rapid adoption across various industries signals that businesses are urgently seeking infrastructure to manage this workforce transformation.
'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,' said Anthony Mironov, Co-founder and CEO of Wingspan. 'The workforce composition is changing, and platforms that plan for this shift now will be well-positioned for the long haul.'
Roughly 40% of U.S. workers have performed contract work in the last year, and businesses increasingly rely on contingent labor to scale efficiently. More than $1.4 trillion dollars is paid out to contractors annually, or 4% of GDP, across an estimated 74 million contractors, per MBO Partners. In many ways, contractors are the backbone of the U.S. economy. By 2027, half of American workers are projected to earn some income from independent contracting, marking one of the most significant shifts in modern employment composition.
Wingspan is utilized by a range of contractors, from Omni's gig workers to CRU Group's insurance adjusters. Teladoc Health, Inc. (NYSE: TDOC) leverages Wingspan to provide its 10,000 healthcare providers with a seamless payment experience, saving the company an average of 28 hours per month on payment processing.
"Working with Wingspan has completely transformed the way Teladoc manages 1099 Provider Payroll,' said Tricia McGimpsey, VP, Payroll at Teladoc Health. 'It's an incredibly seamless process now.'
In addition to its Series B raise, Wingspan is announcing Wingspan Embed, a new solution that enables HR platforms to transform the way they manage and support contractors. The comprehensive feature set goes beyond contractor onboarding, tax automation, and payments to elevate the contractor experience with value-added financial services including tax withholding, debit cards, instant payouts, and insurance. Wingspan Embed's modular and embeddable API-first architecture plugs directly into any HR platform; partners can choose from a white labeled solution, modular pre-built UI components, or a deeper, native integration. With Wingspan Embed, HR platforms become the central hub for managing a modern, flexible workforce.
'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,' continued Mironov. '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.'
The funding will accelerate Wingspan Embed's adoption across HCM and HR platforms while expanding the company's footprint in key verticals—healthcare, insurance, staffing, and professional services—where flexible workforces dominate. Wingspan will continue to invest in its world-class team while launching AI-powered products that apply the latest advances in AI technology to automate contractor compliance, streamline payments, and solve the complex challenges of managing flexible workforces at scale in ways that were never possible before.
'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. '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.'
'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,' said David Ulevitch, General Partner at Andreessen Horowitz.