Wingspan

Automate the business of flexible work.

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Overview

Wingspan is a payroll platform built from the ground up for businesses that run on contractors and freelancers. It automates the entire contractor lifecycle, from onboarding and compliance verification (W-9s, TIN checks) to payments and year-end 1099 tax filing. The platform aims to save finance and operations teams significant time while improving the contractor experience with faster payments and access to benefits.

✨ Key Features

  • Contractor Onboarding Automation
  • W-9 and 1099 Compliance
  • Automated Payments (ACH, Instant Pay)
  • Invoice Generation and Management
  • Worker Benefits (Health, Dental, Vision)
  • Background Checks
  • eSignature for Contracts

🎯 Key Differentiators

  • Purpose-built specifically for the contractor workforce.
  • Focus on automating the entire contractor lifecycle, not just payments.
  • Offers access to benefits for contractors.
  • Strong compliance features for 1099 management.

Unique Value: Wingspan provides a single, automated system to manage the entire contractor relationship, saving businesses time on administration and reducing compliance risk, while also improving the contractor experience.

🎯 Use Cases (4)

Companies that heavily rely on a contingent workforce. Marketplaces and platforms that need to pay a large number of freelancers. Businesses looking to automate their 1099 compliance process. Organizations wanting to offer benefits to their independent contractors to improve retention.

✅ Best For

  • Automating the onboarding and payment of 1099 contractors at scale.
  • Streamlining 1099-NEC form creation, filing, and delivery.

💡 Check With Vendor

Verify these considerations match your specific requirements:

  • Companies that primarily have W-2 employees and only a few contractors.

🏆 Alternatives

Deel Gusto Upwork Lano

Unlike general payroll systems, Wingspan is hyper-focused on the unique needs of managing a contingent workforce, offering deeper features for onboarding, compliance, and benefits for 1099 workers.

💻 Platforms

Web API

🔌 Integrations

QuickBooks Xero NetSuite Slack API

🛟 Support Options

  • ✓ Email Support
  • ✓ Live Chat
  • ✓ Phone Support
  • ✓ Dedicated Support (Enterprise tier)

🔒 Compliance & Security

✓ SOC 2 ✓ GDPR ✓ SSO ✓ SOC 2

💰 Pricing

$199.00/mo

Free tier: N/A

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