Wingspan Raises $24M Series B to Scale Embedded Contractor Management and Capture $1.4T Market

Rhea-AI Summary

Wingspan has secured $24 million in Series B funding led by Touring Capital, bringing its total funding to $54 million. The company, which provides contractor management and payroll solutions, has demonstrated significant growth with a 200% expansion in customer base, 5x increase in average ACV, and has processed over $3 billion in payments.

The company announced Wingspan Embed, a new solution enabling HR platforms to manage contractors with features including tax automation, instant payouts, and insurance. Teladoc Health (NYSE: TDOC), a key client, uses Wingspan to manage payments for 10,000 healthcare providers, saving 28 hours monthly on payment processing.

The funding will accelerate Wingspan Embed's adoption and expand the company's presence in healthcare, insurance, staffing, and professional services sectors.

Positive

• Secured $24M Series B funding, bringing total capital raised to $54M
• Customer base expanded by 200% with 5x increase in average ACV
• Processed over $3B in payments and supports 12x more contractors
• Saves Teladoc 28 hours per month on payment processing for 10,000 providers
• Targeting $1.4T market opportunity in contractor payments

Negative

• None.

Series B led by Touring Capital will propel Wingspan's mission to make flexible work effortless; launch of Wingspan Embed brings comprehensive contractor management to HR platforms

NEW YORK, July 29, 2025 /PRNewswire/ -- 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. 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.

To learn more about Wingspan Embed, visit https://www.wingspan.app/wingspan-embed.

About Wingspan
With 12x growth in contractors served and over $3B in total payments made in the past 3 years, Wingspan is on a mission to make flexible work effortless. As the first payroll platform for independent contractors, Wingspan provides platforms and their customers with the tools to efficiently and effectively manage contractors at scale – ensuring timely payments, access to optional insurance products and simplified onboarding. Wingspan was founded by Anthony Mironov and Greg Franczyk, whose backgrounds in financial services, small business payroll and benefits, and platform engineering gave them the tools to reinvent how companies support the way people work now. Learn more at https://www.wingspan.app/.

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SOURCE Wingspan

FAQ

How much funding did Wingspan raise in its Series B round?

Wingspan raised $24 million in Series B funding led by Touring Capital, bringing its total capital raised to $54 million.

What is Wingspan Embed and what features does it offer?

Wingspan Embed is a new solution that enables HR platforms to manage contractors with features including contractor onboarding, tax automation, payments, tax withholding, debit cards, instant payouts, and insurance.

How does Teladoc Health (NYSE: TDOC) benefit from using Wingspan?

Teladoc Health uses Wingspan to provide 10,000 healthcare providers with seamless payment experience, saving the company an average of 28 hours per month on payment processing.

What is Wingspan's market opportunity in contractor payments?

Wingspan targets a $1.4 trillion market in annual contractor payments, representing 4% of GDP across an estimated 74 million contractors.

How has Wingspan's business grown since its inception?

In less than three years, Wingspan has expanded its customer base by 200%, increased average ACV by 5x, supported 12x more contractors, and processed over $3B in payments.