Full-Time

Engineering Lead Platform

Wingspan

Wingspan

51-200 employees

Freelancer business management and benefits platform

Compensation Overview

$185k - $193.9k/yr

New York, NY, USA

Remote

Remote work allowed from anywhere in the U.S.

Bachelor's

Category
Engineering Management (1)
Required Skills
Software Testing
TypeScript

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Requirements
  • Bachelor's degree or foreign equivalent in Computer Systems Engineering, Computer Engineering, or other closely related field
  • 3 years of progressive, postbaccalaureate experience in Software Engineering
  • Managing complex projects end-to-end, from initial planning and scoping to successful implementation and delivery, ensuring timely completion and alignment with business objectives
  • Software testing methodologies, including unit, integration, and system testing
  • Experience with back-end programming language including Typescript
  • Experience taking broad product requirements and translating them into specific technical requirements and leading team of Engineers
Responsibilities
  • Design, develop, and implement high-quality, scalable software solutions that meet client needs and exceed expectations
  • Collaborate with cross-functional teams to ensure seamless integration and timely delivery of projects
  • Continuously improve and optimize existing software systems by identifying inefficiencies, refactoring code, and implementing best practices
  • Participate in agile development processes, including sprint planning, daily standups, and retrospectives, to ensure project success and team alignment
  • Contribute to growth of engineering culture by sharing knowledge, mentoring new engineer hires, and actively participating in code reviews and technical discussions
Desired Qualifications
  • Telecommuting is permitted from anywhere in the U.S.

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.

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 Jobs

Simplify's Take

What believers are saying

  • July 2025 Series B raised $24 million, bringing total funding to $54 million.
  • Wingspan reported $3 billion processed payments and 12x contractor growth by July 2025.
  • Embedded distribution through Insperity expands reach into thousands of 1099-heavy employers quickly.

What critics are saying

  • Deel, Gusto, and Rippling bundle contractor tools, compressing Wingspan’s pricing by 2027.
  • Insperity partnership dependence creates concentration risk if Insperity renegotiates, builds internally, or stalls adoption.
  • A payment, tax, or misclassification failure triggers fines, lost trust, and enterprise churn.

What makes Wingspan unique

  • Wingspan Embed white-labels contractor onboarding, payments, and 1099 filing inside HR platforms.
  • Teladoc and Insperity validate Wingspan’s contractor workflow integration and enterprise credibility.
  • J.P. Morgan and Lead Bank-backed rails give Wingspan payment reliability and financing depth.

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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%
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.

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.