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Wingspan has raised $24 million in Series B funding to expand its embedded contractor management platform, bringing total funding to $54 million. The company also launched Wingspan Embed, a modular, API-first solution for HR platforms to streamline payments, compliance, and benefits for contractors. With adoption from firms like Teladoc and over $3 billion in processed payments, Wingspan addresses a growing demand for flexible workforce infrastructure.
$24 Million and Counting: Wingspan Doubles Down on the Contractor Economy
Wingspan has secured $24 million in a Series B funding round led by Touring Capital. The raise brings the company’s total capital to $54 million. Existing investors, including Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures, and 186 Ventures, also participated in the round. The investment will support Wingspan’s expansion and further development of its contractor-focused payroll infrastructure.
Why Businesses Can’t Afford to Ignore Contractor Management Anymore
Approximately 40% of U.S. workers have performed contract work in the past year. The contract workforce now consists of an estimated 74 million individuals contributing $1.4 trillion annually, representing about 4% of the U.S. GDP. By 2027, it is projected that half of all U.S. workers will earn income through independent contracting. These figures illustrate a major shift in labor composition, requiring businesses to adapt to new workforce models and support systems.
Inside Wingspan’s Strategy: From Freelancers to Enterprise HR Platforms
Wingspan began by addressing pain points experienced by individual freelancers, such as income tracking, tax management, and access to benefits. Insights gained from serving these workers informed the development of a broader platform that enables businesses to manage and support contractors effectively.
In under three years, the company expanded its customer base by 200%, increased average annual contract value by five times, and scaled its operations to support twelve times more contractors. Wingspan has processed over $3 billion in payments, signaling rapid adoption across a range of industries.
Meet Wingspan Embed: The Tool HR Platforms Didn’t Know They Needed
The company introduced Wingspan Embed, an embeddable infrastructure solution that integrates directly into HR platforms. The tool goes beyond onboarding and payments by offering:
- Tax withholding capabilities
- Instant payouts
- Debit card access
- Insurance options
- Modular, API-first architecture
- White-labeled or pre-built UI components
HR platforms can implement Wingspan Embed either through native integration or modular components, centralizing contractor management and financial tools in a single system.
Recommended: Vanta Raises $150M To Automate Compliance And Help Businesses Prove Trust
Big Names Already Buy In: How Teladoc and Others Use Wingspan Today
Teladoc Health, Inc. uses Wingspan to support over 10,000 healthcare providers, reducing time spent on payment processing by 28 hours per month. CRU Group and Omni also rely on Wingspan to manage their contractors, including insurance adjusters and gig workers. These organizations demonstrate how the platform functions across verticals that depend on flexible labor.
How the New Funding Fuels Expansion and AI Innovation
The new capital enables Wingspan to expand its presence in industries such as healthcare, insurance, staffing, and professional services. The funds will also accelerate the deployment of AI-powered products designed to automate contractor compliance, streamline payments, and handle complex labor force management at scale. In parallel, Wingspan plans to continue building out its internal team to support growth.
Why Investors Are Betting Big on Wingspan’s Vision
Touring Capital described Wingspan as a scalable, intuitive product that addresses a critical market demand. Andreessen Horowitz emphasized the importance of a “contractor stack” for platforms and identified Wingspan as the foundational component. The rapid growth of the company, combined with its adoption by large HR platforms, reinforced investor confidence in its trajectory.
Scaling for the Future of Work—One Contractor at a Time
Wingspan is aligning its platform with the shifting labor landscape by offering businesses a structured way to manage their growing contingent workforces. With the introduction of Wingspan Embed and support from investors, the company is advancing its efforts to serve both contractors and the platforms that manage them.
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