How to Onboard Contractors Twice as Fast

Hiring a full-time employee takes time. You conduct multiple rounds of interviews, deliberate with the hiring team, and do detailed background and reference checks…which can be a months-long process. After all, if you’re hiring someone to join your team 40 hours a week for (ideally) several years, you want to make sure you’re finding the right person. 

When you need a contractor, though, you rarely have the luxury of time. You needed this project done yesterday…and an inefficient onboarding process can drag the entire process down. Or worse, failing to procure the right information at the start can delay payment or tax compliance, giving you a headache down the road.

Even though a contractor may not work for you for more than a few weeks here and there—or may do just one project before riding off into the sunset—it’s important to maximize your onboarding process so you don’t run into issues later (ahem, tax season.) 

Here’s how three different businesses transformed their 1099 onboarding experience, dramatically cutting their contractor onboarding time:

A more efficient onboarding process saves 100+ hours a month

Onboarding starts by collecting the right information for your team to process invoices, conduct tax compliance, and confirm any licensing or certifications for work to begin:

• A signed contract, W9, and NDA if needed
• Identification information like their full legal name, current address, and TIN (either SSN or EIN, depending on their business model)
• A background check
• Insurance and license verification
• Banking details and payment information

That’s a lot of information to handle, especially with a manual process like the one Majestic Services, a family-owned loss control inspection company, used to have. EVP Jake Ciorciari spent hundreds of hours onboarding new inspectors, manually checking payments, and handling contractor emails before they found Wingspan. “I couldn’t afford to waste 2-3 hours every Monday,” says Jake. “It was quickly becoming overwhelming and unsustainable. I knew we needed a better system to automate these brutally manual processes.”

Within a week, they were able to set up an API that automatically sent reports submitted from the Majestic platform into Wingspan for payment. “It’s important that we give our contractors simple ways to sign and access their agreements and Wingspan allowed us to do just that,” he said. 

An onboarding process that scales with you

For a New York-based mental health startup, their explosive growth—reaching 4,000 clients with big names like Microsoft, The Hershey Company, and Fujifilm—meant they needed scale, and fast. Their contractor-based provider pool of 10,000 mental health professionals created a huge administrative burden for their team, who was still keeping track of their payment and tax details in separate systems that didn’t talk to one another.

That meant 1099 filing became super hectic. Not only did they need to track down all of that information—often manually contacting providers one by one for their information—they then had to upload it all by hand. Automation was especially important given the time it took to manually create, reconcile, file and deliver forms to thousands of providers. “In the past, we’d have to manually upload a providers’ W-9 and TIN information which could take more than a week of my time,” said the account manager. “Manually managing that process for thousands of providers is insane.”

Wingspan helped them create a predictable, automated onboarding process they can easily scale as they grow. This made the rest of the contractor lifecycle much more manageable.  “We don’t need all-hands on deck anymore now that we’ve got Wingspan,” said the accounts payable manager. “When you work with thousands of providers like we do, it’s a huge relief to have a trusted partner to help manage the complexity behind that operation.”

One system that handles everything

Claims adjustment firm CRU GROUP runs on a network of more than 1,000 independent insurance adjusters from around the country. This meant reporting and reconciliation processes for its 1099 workforce was incredibly cumbersome, causing plenty of back-office issues every month—and preventing them from scaling up and down to respond to extreme weather and other catastrophic events that require insurance teams on the ground.

“Our W-2 adjusters naturally have longer lead times when it comes to onboarding, but when it comes to our 1099 adjusters, when we call them today, it means we needed them yesterday,” said COO Brett Peiffer. “Our ability to be nimble and responsive is what sets us apart and the efficiency of our back office in many cases, determines how well we’re able to do that,”

Another reason Wingspan appealed to CRU GROUP was its unique ability to offer their adjusters access to competitive health and financial benefits, typically only accessible to full-time W-2 employees. Those benefits included: 

• Telemedicine, vision, dental and life insurance
• Financial management assistance including bookkeeping and banking features
• Access to Wingspan’s team for support on tax, accounting, and benefits 

This would allow the company to better attract and retain independent adjusters while differentiating themselves from other claims adjustment companies in the industry.  “We love the idea of providing adjusters and inspectors valuable health and advisory services,” said David Repinski, CEO of CRU Group. “Access to health services like telemedicine is crucial for adjusters on the road."

In a few short months, the company fully consolidated its onboarding, payment and compliance processes onto the Wingspan platform, resulting in massive efficiencies in its back office and a better experience for adjusters. Identity and payment information, contracts and e-signatures are all now in one place, onboarding contractors twice as quickly as before. “Everything is all in one system with Wingspan,” said Brett.

Why businesses choose Wingspan for contractor management

A smooth onboarding process doesn’t just set your contractor up for success. It starts a long-term relationship with that person—and saves your administrative team time throughout the contractor lifecycle. 

“Wingspan is filling a significant industry need with a world-class platform and we’re excited about the future of this partnership,” said Brett.

With Wingspan, you get:

1. Automation: Onboarding a contractor doesn’t need to take the same amount of time as your full-time employees. Automating the process with real-time TIN verification and automatic invoicing eliminates room for error and gets them on the job more quickly. 
2. Standardization: Creating a repeatable process for onboarding each contractor makes it easier to work with. Every new contractor should get their W9, ACH form with invoicing instructions, and other “working together” info like brand values, key contacts to ask for help, and an overview of the tools they’ll be using.
3. Self-service: Make it easy for contractors to answer their questions as they get to know what it’s like working with you. 

Said Jake, “Wingspan has been a game-changer for our business, saving my team hundreds of hours onboarding inspectors, processing invoices, and running reports.”

‍Manage the entire contractor lifecycle with Wingspan. Learn more >