90%
fewer pay-discrepancy tickets at Teladoc Health, plus $230K a year in time and software costs.
AI-native onboarding, payments, billing and compliance for the flexible workforce: 1099 contractors, international contractors, and contingent W-2 employees
Wingspan's agents save your team time and money, improve worker retention and reduce compliance risk.
Animated illustration of a chat with the Wingspan agent. An operations lead asks it to onboard 214 contractors, release the August pay cycle, sync the batch to QuickBooks, check 1099 readiness, and pull Q3 contractor spend by region. The agent completes each task and reports back, including the rows it held for review, the payments it stopped on failed bank verification, and the regional spend jump it flagged.
Trusted by companies whose flexible workforce is central to how they serve customers.
Read their stories
Purpose-built for flexible work, not retrofitted from W-2 payroll
Onboard & verify
One onboarding flow for every worker you pay.
Tax forms, agreements, payment setup, and work requirements move through one guided flow, whatever type of worker is on the other end.
Invite workers individually or in bulk.
Assign requirements and approval paths by engagement.
Wayfinder reviews supported documents and routes exceptions to your team.
Explore the Platform 
One worker record for your whole flexible workforce
One worker record, one compliance engine, and one audit trail—available to your team and the agents you authorize through MCP.
Permissions Approvals Audit trail MCP
Onboard & verify workers
Bring every worker through one guided setup and verification flow.
Manage work & approvals
Keep assignments, work, rates, requirements, and decisions connected.
Worker payments (AP)
Turn approved work into accurate worker payments.
Billing (AR)
Turn approved work into client invoices and collect revenue.
Tax & 1099 compliance
Keep tax details, reportable payments, filing, and corrections connected.
Support your workers
Give workers self-service status, specialist support, and resources.
Onboard & verify workers
Bring every worker through one guided setup and verification flow.
Manage work & approvals
Keep assignments, work, rates, requirements, and decisions connected.
Worker payments (AP)
Turn approved work into accurate worker payments.
Billing (AR)
Turn approved work into client invoices and collect revenue.
Tax & 1099 compliance
Keep tax details, reportable payments, filing, and corrections connected.
Support your workers
Give workers self-service status, specialist support, and resources.
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
