Wingspan

Wingspan

Platform for freelancers' business management

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

Fintech

Healthcare

Legal

Company Size

51-200

Company Stage

Series A

Total Funding

$17.5M

Headquarters

New York City, New York

Founded

2019

Overview

Wingspan provides a platform that simplifies business operations for freelancers and self-employed individuals. It offers tools for invoicing, expense management, tax handling, and customizable contract templates, helping users manage their administrative tasks efficiently. A key feature is the Pro plan, which includes access to a Care Advocate for healthcare navigation and custom insurance packages, giving freelancers benefits typically available to larger company employees. Wingspan operates on a subscription model, starting at $20 per month, and partners with agencies to manage payments and compliance for 1099 contractors. The goal of Wingspan is to streamline the business processes of freelancers, making it easier for them to focus on their work.

Simplify Jobs

Simplify's Take

What believers are saying

  • Wingspan raised $14M in Series A funding, boosting its growth potential.
  • The rise of the gig economy increases demand for Wingspan's freelancer-focused services.
  • Integration with AI-driven financial planning tools could enhance Wingspan's platform.

What critics are saying

  • Increased competition from AI-driven platforms like Onix's Wingspan could overshadow current offerings.
  • Traditional financial institutions adapting to the gig economy may reduce Wingspan's market share.
  • Reliance on partnerships for payment and compliance services poses financial and regulatory risks.

What makes Wingspan unique

  • Wingspan offers a comprehensive platform for freelancers to manage income, benefits, and taxes.
  • The Pro plan includes a Care Advocate to help users navigate healthcare options.
  • Custom insurance and benefits packages provide freelancers perks typically reserved for larger companies.

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Funding

Total Funding

$17.5M

Meets

Industry Average

Funded Over

2 Rounds

Notable Investors:
Series A funding typically happens when a startup has a product and some customers, and now needs funding to scale. This money is usually used to grow the team, expand marketing, and improve the product. Venture capital firms are frequently the main investors here.
Series A Funding Comparison
Meet Average

Industry standards

$15M
$8.2M
Discord
$14M
Wingspan
$15M
Canva
$30M
Kalshi

Benefits

Flexible Time Off

Stock Options

Home Office Stipend

401(k) Company Match

Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

-6%

1 year growth

0%

2 year growth

-4%
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.

PYMNTS
Mar 1st, 2024
Platforms Pave Way For Gig Workers Forging New Paths To Financial Independence

The rise of the gig economy has transformed work for millions of individuals. From freelance creatives to ridesharing drivers, gig workers are pursuing financial independence on their terms, redefining the traditional notions of employment. However, achieving financial security in a flexible work environment can be challenging due to inconsistent income and complicated tax and benefit systems, posing significant hurdles for gig workers today. In this dynamic landscape, traditional financial institutions (FIs) have struggled to keep pace, leaving a void that FinTech firms, platforms and smaller banks are now trying to fill

ExploreBit
Mar 17th, 2023
Wingspan raises USD 14M Series A

Wingspan, the first payroll platform purpose-built for flexible workforces, today announced it has raised a $14 million Series A led by Andreessen Horowitz, bringing its total capital raised to $23.5 million.

Finsmes
Mar 16th, 2023
Wingspan Raises $14M in Series A Funding

Wingspan, a New York-based provider of a payroll platform purpose-built for flexible workforces, raised $14M in Series A funding.

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