Wingspan vs. Stripe
Wingspan: The Best Stripe Connect Alternative for Contractor Payments
Stripe Connect is an API for payments. Wingspan is an end-to-end operating system designed to manage your contingent workforce without the heavy engineering lift.
- Full 1099 lifecycle management with zero engineering required
- Real-time TIN matching and automated IRS 1099 e-filing
- Automated pay calculations and mass payouts in one workflow
SM
Sarah Mare
Fresh Designs
Approved
SH
Sakhi Halle
Halle Adjusters
Approved
BV
Blake Vernon
Green Garden Caregivers
Approved
Nursing hours $2,800.00
Sync
qb
ADP
Trusted by businesses that run on contingent work.
Wingspan vs. Stripe
Full Contractor Lifecycle Platform
Bulk Onboarding at Scale
Automated Tax Filing & Compliance
International Payments
Auto-Computed Payouts
Multi-Entity ERP Sync
Accounting System Integration
Real-Time TIN Verification
Tax Withholding for Contractors
Quarterly Estimated Tax Payments
Instant Payouts & Fee Control
Contractor Benefits & Retention
Contractor Self-Service Help Desk
Embeddable API / White-Label
Wingspan
Full Contractor Lifecycle Platform
Bulk Onboarding at Scale
Automated Tax Filing & Compliance
International Payments
Auto-Computed Payouts
Multi-Entity ERP Sync
Accounting System Integration
Real-Time TIN Verification
Tax Withholding for Contractors
Quarterly Estimated Tax Payments
Instant Payouts & Fee Control
Contractor Benefits & Retention
Contractor Self-Service Help Desk
Embeddable API / White-Label
Stripe
Full Contractor Lifecycle Platform — (API only)
Bulk Onboarding at Scale
Automated Tax Filing & Compliance
International Payments
Auto-Computed Payouts
Multi-Entity ERP Sync
Accounting System Integration — (Limited)
Real-Time TIN Verification
Tax Withholding for Contractors
Quarterly Estimated Tax Payments
Instant Payouts & Fee Control
Contractor Benefits & Retention
Contractor Self-Service Help Desk
Embeddable API / White-Label
Wingspan is the only platform that handles all the unique processes of contingent work at scale.
Compliance
Offload 1099 creation, filing, and delivery.
Reclaim your January with Wingspan managing your entire 1099-NEC process.
Convenient contractor help desk for questions and corrections
Automatically generate 1099-NEC forms
Secure, compliant filing and delivery

An all-in-one flexible work platform that delivers real results.
Streamline your operations
$25,000
saved offloading busy season work and automating your critical workflows.
Attract and retain talent
20%
reduced churn by paying your workers faster and more conveniently.
Ensure compliance
$50,000
avoided for each compliance breach related to misclassification.
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
Wingspan integrates with these tools + many more