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Wingspan

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One place for freelancers to manage income, benefits and taxes

New York City, United StatesFounded 2019Fintech
Valuation $100–250M Last recorded · 2025
Revenue $10–50M Latest reported FY
Headcount 100–500 Current team size
Total funding $10–50M Disclosed equity funding
Unlock exact values This page shows ranges. Dealroom has the exact numbers for Wingspan and the history behind them.

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 data

At a glance

Status
Operational
Founded
2019
Headquarters
New York City, United States
Employees
129
Open positions
3
Dealroom signal
81.7/100
Industry
Fintech
Sub-industry
Financial Management Solutions
Sector
Fintech
Business model
SaaS
Client focus
b2c

Funding history

6 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
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 ↗
Showing the latest 2 of 6 recorded eventsBook a demo for the full funding history →

Financials

Revenue over time

Revenue, earnings and other financial measures where available. Years marked “E” are estimates.

YearRevenueGrowth
2026
2025
2024
2023
2022
2021 —
Company filings, research estimates and Dealroom dataBook a demo for the full financial model →

Growth signals

Wingspan website traffic

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.

Latest monthly visits160K 3-month web change+6.7% 1-year team growth+4.9%
Summary metrics are public; monthly history is available with a demoCompare with peers →

Similar companies

Closest operating peers by Dealroom taxonomy

Company identity and context are open; selected comparison metrics preview what is available on the platform.

Showing 8 of the closest matchesCompare every metric →

Investments and acquisitions

Capital deployed

Recent portfolio relationships for companies that also act as investors or acquirers.

Investors

12 investors on the cap table

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
Team profiled 7 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 2 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
7 countries with
team presence
🇺🇸 United States71.4%
🇵🇱 Poland9.5%
🇨🇦 Canada4.8%
🇮🇳 India4.8%
🇺🇦 Ukraine4.8%
Top 5 of 7 shown

Market sentiment

Posts on X, past 7 days

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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