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.
Manage work & pay
Keep work, terms, and payments connected.
Wingspan keeps assignments, completed work, rate calculations, and decisions on one operating record. Your approved assistant can use live MCP tools with the permissions you assign.
Set terms, rates, requirements, and approval paths by engagement.
Turn approved work into ready-to-review payables.
Use MCP to search records, create payables, and route approvals without a shared login.
Bill & stay compliant
Turn approved work into revenue—and keep tax records ready.
Client billing, worker payments, tax readiness, and workforce spend stay connected to the same operating record.
Build client invoices from the work your team approved.
Keep tax details and reportable payment totals current all year.
Use MCP to ask about filing readiness and workforce spend by region.
Support your workers
Give workers a clear place to get help.
Workers can check status, find answers, contact support, and manage available resources without sending every question back to your team.
Self-service visibility into onboarding, payment, and tax status.
Tier 1 support with context from the worker record.
Optional contractor resources, distinct from employee benefits.
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.
“
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.
“
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.
“
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