Automate 1099 Compliance Before the January Rush

Automate W-9 collection, TIN verification, and contractor communications with Wingspan — so your team can enter 2026 calm, compliant, and confident.

  • Automated W-9 Collection
  • Real-Time TIN Verification
  • Contractor Self-Service Portal
Schedule a 30-Minute Tax Season Consultation
Meet 1:1 with a Wingspan expert to review your current 1099 workflow and uncover quick wins to simplify compliance before year-end.
You’re all set! Next step: book your demo to reserve your consultation time. We’re looking forward to showing you how Wingspan can make this 1099 season stress-free.
Trusted by businesses that run on contingent work.

1-click creation and filing of Form 1099-NEC

Wingspan automatically generates your 1099-NEC forms and handles e-filing with the IRS and states. For contractors, Wingspan delivers their 1099s to them via mail and the Wingspan app.

Wingspan has verified W-9 data and knows what you’ve paid your workers, making it easy for us to generate all your 1099s with a single click.

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Contractor portal with reminders and 1099 corrections

Contractors can easily download their 1099 from the Wingspan portal and see what payments make up their 1099 amount.

Wingspan keeps contractors in the loop during the process. Contractors get a reminder prior to filing to confirm personal information and 1099 delivery format. After filing, contractors can suggest a correction. Wingspan handles resolving suggestions and re-filing the 1099.

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Audit-ready and built for scale

Wingspan provides audit logs that include correction justifications and TIN verification with easy IRS data-pack exports.

Easily handle high volumes of 1099. Wingspan scales when your team cannot.

Permissions and delegation of approvals lets you distribute 1099 duties across segment owners on large AP teams. Even sub-entities are a breeze with built-in access controls.

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An all-in-one flexible work platform 
that delivers real results.

$50'000

avoided for each compliance breach related to misclassification

1.5

hrs saver per 1099 during tax season

100%

elimination of compliance risk of missing 1099 deadlines

Wingspan is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. The Wingspan Visa® Debit Card is issued by Lead Bank pursuant to licensing by Visa® U.S.A. Inc., both only available to eligible commercial entities. Terms and conditions apply.

Meet the finance and operations leaders raving about Wingspan.

“
The Wingspan system is incredibly seamless and has completely transformed the way Teladoc manages 1099 Provider Payroll.
Tricia McGimpsey
VP of Payroll, Teladoc
Industry
Telehealth
No. of Workers
10,000
“
Our partnership with Wingspan has been transformational.
Lisa Zeeveld
CFO, BELAY Solutions
Industry
Virtual Staffing Solutions
No. of Workers
7,000
“
The best freelance payroll solution I’ve come across.
Jimmy Daly
CEO, Superpath
Industry
Media & Marketing
No. of Workers
100
“
We're growing our network of 1099s using Wingspan.
Srini Srinivasan
CFO, Fizz Social
Industry
Social Network Platform
No. of Workers
2,000
“
Wingspan helps us significantly cut the number of calls we receive from our 1099 adjusters.
Bret Peiffer
COO, CRU Group
Industry
Insurance Claims
No. of Workers
1,000
“
Wingspan helps us save costs on financial reporting, tax compliance and invoice management.
Bill Brassfield
CEO, Pacesetter Claims Service
Industry
Insurance Claims Adjusting
No. of Workers
3,000