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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.

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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 SoftwareEnterprise SoftwareFintechHealthcare

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

  • September 22, 2026 MCP beta expands Wingspan into finance and operations AI workflows.
  • July 29, 2025 Series B raised $24 million, signaling investor backing for expansion.
  • Wingspan reported 300,000 workers and $8.0 billion annualized volume, proving real usage.

What critics are saying

  • WorkSuite and ADP WorkMarket attack Wingspan's U.S.-first niche with broader enterprise suites.
  • Wingspan's AI assistant layer is easy for competitors to copy by 2027.
  • If embedded partners like Insperity switch vendors, Wingspan loses distribution and transaction volume.

What makes Wingspan unique

  • Wingspan bundles contractor onboarding, payments, billing, and compliance in one system.
  • Its September 22, 2026 MCP beta plugs Wingspan into Claude and ChatGPT.
  • Insperity and Teladoc validate embedded contractor management and healthcare-provider payment workflows.

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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
$45M
$65M
$100M

Benefits

  • Flexible Time Off
  • Stock Options
  • Home Office Stipend
  • 401(k) Company Match
  • Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

-5%
Small Business PR
Sep 22nd, 2026
Small business news releases.

Small business news releases. Wingspan introduces MCP to bring flexible worker onboarding and payables into your team's AI assistant. NEW YORK, Sept. 22, 2026 /PRNewswire/ - Wingspan, the AI-native platform for onboarding, payments, billing and compliance for the flexible workforce, announced Wingspan MCP, a connection that lets finance and operations teams work in Wingspan through their own AI assistant. Finance and operations teams can check onboarding progress, prepare payables, and understand payment history through Claude and ChatGPT, with final approval and payment execution completed in Wingspan. Wingspan serves companies that manage and pay 1099 contractors, international contractors, and contingent W-2 employees. The MCP beta focuses on everyday worker onboarding and payables work: discovering what is blocking onboarding, inviting workers, reviewing what's owed and what's been paid, creating draft payables, understanding payment history, and previewing upcoming payroll runs. For a finance team preparing a payment run, the work starts before money moves. Someone needs to confirm who is ready to pay, check what each person is owed, and resolve questions about earlier payments. Operations teams need to know which workers have completed onboarding and which requirements remain outstanding. When those answers require manual exports and cross-checks, routine questions take time away from the work itself. Wingspan MCP brings those tasks into the AI tools teams use. Wingspan connects the worker record with onboarding requirements, work, billing, payments, and compliance, and MCP gives a customer's own assistant access to that system so the team can use the underlying records to answer questions and prepare work for review. Wingspan MCP is launching in beta for Claude and ChatGPT. About Wingspan: Wingspan is the AI-native platform for onboarding, payments, billing and compliance for the flexible workforce: 1099 contractors, international contractors, and contingent W-2 employees. With over 300,000 workers served and over $8.0 billion in annualized transaction volume, Wingspan brings worker records and workforce operations together so finance and operations teams can manage the work and the payments in one system. SOURCE Wingspan

Business Wire
Sep 12th, 2026
Wingspan Announces $14M Series A Led by Andreessen Horowitz

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

Boards & Swords
Jul 10th, 2026
Sew ewe Want To Be A Game Master - boards & swords #288.

Sew ewe Want To Be A Game Master - boards & swords #288. Wingspan will soon fit in your pocket, Spirit Island is getting a new publisher, and the Lazy Gamemaster has a brand new kickstarter campaign! Speaking of being a GM, if you want to be a better one, you'll want to check out its review of "So You Want To Be A Game Master" by Justin Alexander (amazon affiliate link). Then, we'll give you some examples of "great" GM advice in its Ask A Dirtbag GM segment! Join Boardsandswords on Discord! News. Beloved bird board game Wingspan announces a pint-sized Pocket version (from Wargamer) Wingspan is getting a small, standalone version of the game to make it more accessible and beginner friendly. Although Philip had the best idea during the show and this version should only have featured small birds, but I doubt that will actually be the case. The gameplay has been tweaked, so you won't be able to use these cards alongside your normal wingspan cards, but if you've been at the bar and had a itch to learn more about birds, soon it'll be much easier to pull a game out to do so (you'll still probably get weird looks). It's kind of telling when you say "we avoided Kickstarter because we didn't want to play into the forced immediacy", and then you pull a Kickstarter because it didn't get enough attention - even though it funded. Yeah, everyone knows that setting a low goal and trying to get multiple times that goal is how you run a Kickstarter, but I really think that the funding goal should at least be profitable for your company in some small regard. Otherwise what's the point? When a company spends its time and money laying off employees, it shouldn't surprise them when creators don't want to work with them anymore. Flat Iron Group is finding themselves in that position with Spirit Island, which had been one of their biggest hits. The creator of the game let their contract with the publisher expire after Flat Iron spent most of 2025 downsizing and letting go of a lot of staff. Now, the creator is in talks with an unnamed publisher to bring back the popular board game with all new art. Who doesn't like JRPG inspired D&D content, especially when they feature sexy anime foxy ladies! This sourcebook adds lots of 5e content surrounding a goddess of trickery. I may or may not have backed this one during the show - but at least I didn't get the contoured mousepad! (At least, not yet). Mike Shea has done a great job over the years giving people tips on how to improve their games without going too overboard. He's back on Kickstarter with "Rise of the Lazy Gamemaster", a new book further expanding on these concepts. I've read a couple of his books, and there is some great content in there. So much, that I went and got him to come on the show next time as a guest! I'm so excited!!! Ask A Dirtbag GM. Boardsandswords has all been there - you need to describe a scene, so you type out a monologue of a description, only to see your players' eyes glaze over. Or, you do the opposite and just talk about the monsters in the room. There's got to be a happy medium, right? I definitely picked this thread because some of the resources Boardsandswords talk about in the news and the Justin Alexander book will be very helpful in answering this question. This DM has an aquatic adventure, but their players have found out that the "shape water" spell can be a bit of a game breaker when you are at sea. Or can it? Maybe this DM needs to implement some consequences to using the spell to "discourage" players from this type of behavior. Or, just make the spell act differently than the way their players *think* it will work (but still within the description of the spell). Anything to change up the game and keep players from just powering through an adventure with very little effort. Affiliate links/codes: help support the show! Monument Hobbies: 5% off using code "boardsandswords" at their checkout: https://monumenthobbies.com/ Email Boardsandswords your comments and questions at [email protected]. Boardsandswords is on social media! You can find Boardsandswords on Facebook & Instagram @boardsandorswords! You can also help support the show and get extra bonus content by pledging just $1/month at https://patreon.com/boardsandswords. Thank you for listening to the show. Until next time, remember that every gamer has a story...what's yours? July 10, 2026

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.

HRHub
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.

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