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Wingspan
One place for freelancers to manage income, benefits and taxes
About Wingspan
Wingspan is a startup that provides a comprehensive platform designed to simplify the business operations of freelancers and self-employed individuals. The company operates in the gig economy market, catering primarily to independent professionals who need to manage various aspects of their business, such as invoicing, taxes, contracts, and benefits.
Wingspan's platform offers essential tools that help freelancers streamline their administrative tasks. This includes sending invoices, managing expenses, and handling tax-related matters. The platform also provides customizable templates for contracts and proposals, making it easier for users to maintain professionalism in their business dealings.
One of the standout features of Wingspan is its Pro plan, which includes access to a Care Advocate. This service helps users navigate their healthcare options, ensuring they get the coverage they need. Additionally, the platform offers custom insurance and benefits packages, giving freelancers access to perks typically reserved for employees of larger companies.
Wingspan's business model is subscription-based, with plans starting at $20 per month. This model provides a steady revenue stream while offering users a cost-effective solution to manage their freelance business. The company also partners with agencies and employers to handle payments and compliance for 1099 contractors, further expanding its market reach.
In summary, Wingspan makes money by offering subscription plans to freelancers and partnering with agencies for payment and compliance services. The platform is designed to make it easier for self-employed individuals to manage their business operations, from invoicing to benefits, all in one place.
Source: Dealroom company dataKnowledge graph
More headlines
Funding history
Company financing events and reported valuations.
| Deal type | Date | Amount | Valuation | Investors | Source |
|---|---|---|---|---|---|
| SERIES B✓Equity / VC | Jul 2025 | $24M | $96M | 186 Ventures · Distributed Ventures · Company Ventures · Andreessen Horowitz | ↗ |
| SERIES A✓Equity / VC | Mar 2023 | $14M | $56M | Andreessen Horowitz · Ludlow Ventures · Long Journey Ventures · Distributed Ventures | ↗ |
Financials
Revenue, earnings and other financial measures where available. Years marked “E” are estimates.
Growth signals
Latest recorded traffic for Wingspan is 160K monthly website visits, up 6.7% over the last three months. Wingspan's team grew 4.9% over the past year.
Open positions
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Investments and acquisitions
Recent portfolio relationships for companies that also act as investors or acquirers.
Investors
From Dealroom's funding and investor records, grouped by the round each investor first entered.
Seed1 investor entered at this stage
Company Ventures
Series A6 investors entered at this stage
Andreessen Horowitz
Ludlow Ventures
Long Journey Ventures
Distributed Ventures
186 Ventures
Touring Capital
Other known investors5 additional known investors
Grand Central Tech
NFP Ventures
Awesome People Ventures
GoodFriends
Swift Ventures
Source: Dealroom Talent Intelligence.
Global footprint
team presence
Market sentiment
An AI-synthesised read of the highest-engagement posts about Wingspan on X, ranked by likes and reposts, corporate channels excluded.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
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