Wingspan

Wingspan

Freelancer business management and benefits platform

Overview

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.

About Wingspan

Simplify's Rating
Why Wingspan is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Consumer Software

Enterprise Software

Fintech

Healthcare

Company Size

51-200

Company Stage

Series B

Total Funding

$41.5M

Headquarters

New York City, New York

Founded

2019

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Simplify's Take

What believers are saying

  • $24M Series B from Touring Capital fuels 200% customer growth and $3B payments processed.
  • Insperity partnership enables seamless 1099 worker onboarding and payments.
  • Teladoc Health saves 28 hours monthly streamlining contractor payments with Wingspan.

What critics are saying

  • Upwork Enterprise captures mid-market B2B2C segment in 12-18 months.
  • DOL crackdown turns compliance tools into liability vectors within 12-36 months.
  • Stripe launches native contractor payroll, eroding Wingspan's edge in 12-18 months.

What makes Wingspan unique

  • Wingspan Embed automates contractor onboarding, payments, and compliance for HR platforms.
  • Pro plan offers Care Advocate for healthcare navigation and custom benefits packages.
  • Automatic licensing verification reduces compliance risks during inspector onboarding.

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Funding

Total Funding

$41.5M

Below

Industry Average

Funded Over

3 Rounds

Notable Investors:
Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Below Average

Industry standards

$35M
$30M
Patreon
$45M
Linktree
$65M
Substack
$100M
ClickUp

Benefits

Flexible Time Off

Stock Options

Home Office Stipend

401(k) Company Match

Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

0%

2 year growth

0%
Market Wire News
Jul 29th, 2025
Wingspan Raises $24M to Scale Operations

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.

HR Hub
Jul 22nd, 2025
Insperity Partners With Wingspan To Launch First Contractor Management Solution, Enabling Seamless Onboarding And Payments For 1099 Workers

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.

AlleyWatch
May 13th, 2025
The AlleyWatch Startup Daily Funding Report: 5/13/2025

Wingspan, a payroll platform for businesses that use contractors, has raised $20M in funding according to a recent SEC filing.

Express Computer
Apr 10th, 2025
Onix introduces Wingspan: A revolutionary industry-first multi-capability agentic AI platform for enterprises

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.

Meridio
Apr 4th, 2025
Health Insurance for 1099 Contractors: Navigating the Landscape

For platforms like Wingspan, partnering with Meridio, a provider specializing in affordable health benefits for contractors, was a game-changer.

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