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Introducing Wingspan 2.0: Bill clients, onboard and pay workers, and stay compliant

By 
Anthony Mironov
November 28, 2023

The rapidly evolving labor market has given rise to a revolution in the way we work: today one out of three Americans is an independent contractor, and their work contributes more than a trillion dollars a year to GDP. This shift has highlighted an administrative crisis for businesses that rely on contingent work to drive revenue. Payroll, bill payment, and benefit systems weren’t designed to handle the new reality. They were built for a world that revolves around the W2. 

When we founded Wingspan less than four years ago, the tension between the promise of flexible work and its compromises was already clear. A lot has changed since then, but the system of record for freelance work hasn’t. Until now. 

We’ve partnered with more than 30,000 contractors and processed over $1 billion in transactions. We’re trusted by hundreds of businesses that rely on flexible workforces to drive revenue, and we’ve saved them all thousands of dollars and countless headaches — and learned a lot along the way. 

That's why we're excited to announce Wingspan 2.0, the first payroll platform that automates the entire contractor lifecycle, all in one platform. For the first time ever, businesses can streamline onboarding, automate payments, offload 1099 processing and provide access to best-in-class financial and health benefits that drive retention.

A flexible work platform for flexible work businesses 

Wingspan offers companies that rely on contingent work the tools to automate the full lifecycle of flexible work across four key use cases:

  • Streamline and control onboarding and eligibility 
  • Automate invoicing and payments from AR to AP
  • Offload 1099 creation, filing and delivery 
  • Provide workers with access to health and financial benefits

Streamline and control onboarding and eligibility

Stop wasting time chasing W-9s and give your workers an easy way to get verified. Now, you can kick off onboarding with just one email, from background and TIN checks to W-9 and eSignatures, Wingspan has you covered. Use us for everything or integrate existing parts of your onboarding process to get the whole thing under one control point. Workers can go back to Wingspan at any time to change their profile and re-verify documentation, making Wingspan your go-to and getting you out of the constant back and forth of emails and calls with workers.

Streamline and control onboarding and eligibility

Automate invoicing and payments from AR to AP

Your flexible workforce is your business. Finally there’s a payments platform that understands the connection between AR and AP, so you can link work done to your client invoices, and let Wingspan automatically tabulate your contractor’s pay. Wingspan can generate invoices automatically, resolve disputes, and with simple approval pay all your contingent staff. Contractors enjoy flexible payment options with our platform supporting ACH, debit, credit, and instant transfers to debit cards and bank accounts.

Automate invoicing and payments from AR to AP

Offload 1099 creation, filing, and delivery

You can auto-generate 1099s with just a few clicks. Wingspan swiftly e-files with the IRS and states and delivers 1099 forms directly to contractors. Free your team from the burden of contractor tax form questions. Wingspan’s contractor help desk assists your contractors with common issues and form corrections can be requested and approved in-app.

Offload 1099 creation, filing, and delivery

Provide workers with access to health and financial benefits

Wingspan enables you to run an efficient flexible work business that stands out from your competition by providing contingent workers with access to complete health and financial benefits. This gives workers the perks of full-time employment and improves retention, without adding classification risk. Benefits include business checking accounts and debit cards for workers, curated insurance options, and the financial tools they need to run their business.

Provide workers with access to health and financial benefits

Get started with Wingspan by saving thousands with free 1099 filings 

We also made it easier to get started with Wingspan, with simpler pricing and a product that will get you up and running in just a few minutes. We can’t wait to show you, so we’re launching our first-ever promotion

Switch to Wingspan by December 31st & we'll file your 2023 1099s for free. Find out how.

Thank you

None of this would be possible without the unrelenting effort of our team, our investors, and our incredible customers. A huge thank you to everyone believing in our vision and supporting us in our quest to revolutionize the future of work. We are so excited about the powerful platform we built and the amazing things to come as we transform the way flexible work businesses operate and improve the lives of workers. The work is just beginning. 

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