INSPERITY CONTRACTOR MANAGEMENT powered by Wingspan
Redefine how you manage contract workers
Our comprehensive platform helps you streamline onboarding, payments and 1099 issuance.
Benefits of Insperity contractor management
Speed of service
Faster payment processing and delivery to contractors with flexible instant payout methods
Less hassle
Fewer support tickets daily with real-time payment transparency
Time savings
Drastically reduce time spent on 1099 form creation, issuance and delivery
Streamline onboarding and W-9 collection
Stop chasing down W-9s and reduce compliance risk by giving workers an easy way to get verified. This self-service portal allows contractors to update information on their own. You can onboard contractors online individually or collectively and leverage robust policy management, setting specific requirements for multiple different contractor groups.

Automate invoicing and payments
You’ll be able to automate payments, 1099 tax compliance, billing, expense reimbursement and more. Plus, you can pay faster with transparency into invoicing and payment details. Built for both companies and contractors, this platform supports invoice creation with a wide range of payment methods available.
Create, file and deliver 1099s
With this secure technology, you can automate the entire 1099 process from creating forms to fixing errors and filing with the IRS. Our convenient help desk is available to answer questions about the platform and how your business can get set up.


Offer contractor support
Your contractors have access to vetted, licensed insurance brokers for health, dental, vision, life and business insurance,+ as well as a help desk for support. You’ll also be able to provide access to free, optional financial software, banking solutions, tax management, a document vault and templates to help them run their businesses better.
+Insurance not provided by Insperity. Available through third-party providers for an additional fee.
Learn more about Insperity contractor management
Check out our resources to see how you can better manage your contingent workforce.
How to confidently manage 1099 contractors as your business grows
Discover more about this purpose-built platform
Learn how Insperity’s HR solutions can help
transform your business
Insperity contractor management, powered by Wingspan, is an additional fee-based service and requires execution of additional documents.
