Do your benefits work for your contractors?

Our employer-sponsored financial and health benefits platform provides the essential tools your contractors need for their business and health.
Financial benefits

Take the stress out of taxes.

Taxes and bookkeeping are a distraction & headache that full-time employees don’t face. Offer your contractors free automated tax withholdings and payments to the IRS.
“During tax season, I was running around like a chicken with a head cut off. Wingspan takes that stress out of my life.”
Terry Warner
Brand Designer
Actual results vary by customer
June net paycheck
Estimated Tax
Your earnings
Tax Withholding
Automatically set aside from income in an FDIC-insured account. A few basic questions and we can tell your contractor how much federal and state tax they owe
My estimated tax rate is
This rate is set aside from all payments when withholdings is on.
Update tax profile
Federal & State Payments
Make a quarterly or annual payment without leaving Wingspan. Payments in all 50 states.
complete your Q1 filing
Deductible Expenses
Estimated Tax Payment
Submit Estimated Tax Payment
Income & Expense Tracking
Link your bank account, and automatically track income and identify deductible business expenses. At tax return season, export tax-ready financials.
Your 2021 tax documents are ready
You projected to save $4,095.64 on your tax payments wiht the deductions we found.
2020 Schedule C PDF

Why companies love Wingspan

We are able to uniquely offer freelancers benefits such as tax withholding, health care which help us retain and recruit adjusters.
Bill Brassfield
CEO, Pacesetter Claims Service
Actual results vary by customer
Improves retention & recruitment


average reduction in contractor turnover.
Increase contractor satisfaction


of contractors prefer an employer who offers health & financial benefits.
Member name
phone number
Financial benefits

Concierge support for life's unexpected moments

Financial Helpline Take on major life changes with live one-on-one coaching from accredited financial counselors.
Tax Hotline Free tax return preparation and year-round support from tax experts whenever you need it.
Legal Access Get legal support with free and discounted services from experienced lawyers.
Explore all 72 benefits
Financial benefits


Enable your contractors to send approvable invoices and retainers. Wingspan gives your contractors everything they need to get paid.
Custom invoices
Set up clients on retainer, add late fees, and manage who pays for processing fees.
Easy subcontractor payments
Manage and pay collaborators & subcontractors.
Payment tracking
Get notified for invoices approvals, payments and deposit dates.
Personal payment link
Share a personal pay link. Get paid. That simple.
Explore all 72 benefits
Invoice activity
Paid Jan 24, 2021
$2,000.00 deposited to Chase *8456
Reminder sent to Alice Rosen
Feb 20, 2020 at 4:30pm
HEALTH benefits

Health, Vision & Dental Insurance

Contractors are responsible for their own insurance. Give them peace of mind with discounted group rates for Health, Vision and Dental insurance. All accessible and managed through Wingspan.
Explore all 72 benefits
Your Benefits
Open Access Plus
Member ID: 2398409834

Big-company Benefits

Offer free, subsidized or paid access to big-company non-insurance benefits.
24/7 Teladoc telemedicine
Virtual counseling
Discounted medicine
Virtual counseling
Perscription savings


Reduce liability by securing your data
Explore Security

Onboarding & compliance

Effortless onboarding & streamlined payments
Explore Onboarding

Streamlined payments

Transparent & timely payments
Explore Payments

Contractor benefits

Benefits full-time employees will envy
Explore Benefits

Easy integration & reporting

Gain transparency into workforce by synching Finance, HR & Project Management tools
Explore Integrations

With Wingspan, onboard, pay, and support contractors effortlessly

Retain your workforce, mitigate risk, eliminate drudgery and create new opportunities