Full-Time
Posted on 5/20/2025
Freelancer business management and benefits platform
No salary listed
Canada
In Person
Wingspan provides a subscription platform that helps freelancers and self-employed individuals manage the day-to-day parts of running a freelance business. The software lets users send invoices, track expenses, handle taxes, and manage contracts and proposals through customizable templates, all in one place. A standout Pro plan includes a Care Advocate to help navigate healthcare options and access to custom insurance and benefits packages typically available to larger employers. The platform also partners with agencies and employers to handle payments and compliance for 1099 contractors. This combination gives freelancers a centralized, affordable way to run their business and access benefits. Wingspan’s goal is to simplify administrative tasks for freelancers, provide steady revenue through subscriptions, and expand its market by offering payment and compliance services to agencies and employers.
Company Size
51-200
Company Stage
Series B
Total Funding
$41.5M
Headquarters
New York City, New York
Founded
2019
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Flexible Time Off
Stock Options
Home Office Stipend
401(k) Company Match
Wellness Program
Wingspan raised $24 million in Series B funding led by Touring Capital, totaling $54 million raised. The funds will scale Wingspan Embed, a contractor management solution for HR platforms. Wingspan has grown its customer base by 200% and processed over $3 billion in payments. Teladoc Health uses Wingspan to streamline contractor payments, saving 28 hours monthly. The funding will expand Wingspan's reach in key sectors and enhance its AI-powered products for managing flexible workforces.
New York, NY /PRNewswire/ - Wingspan, the first modern payments platform purpose-built for independent contractors, today announced a new strategic partnership with Insperity, Inc. (NYSE: NSP), a leading national provider of human resources and business performance solutions.
Wingspan, a payroll platform for businesses that use contractors, has raised $20M in funding according to a recent SEC filing.
Unveiled at Google Cloud Next 25, Wingspan empowers enterprises to create advanced, context-aware data platforms and deploy domain-specific AI agents, leading to enhanced user productivity and actionable AI-driven insights.
For platforms like Wingspan, partnering with Meridio, a provider specializing in affordable health benefits for contractors, was a game-changer.