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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.
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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Total Funding
$41.5M
Below
Industry Average
Funded Over
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Industry standards
Flexible Time Off
Stock Options
Home Office Stipend
401(k) Company Match
Wellness Program
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
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.
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.
Wingspan, a payroll platform for businesses that use contractors, has raised $20M in funding according to a recent SEC filing.
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.
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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
Find jobs on Simplify and start your career today