2 Days → 2 Hours: How 3 Businesses Completely Transformed Their Payroll Process

Payroll for your full-time W2 employees is relatively straightforward. Salaried employees expect a paycheck every two weeks directly in their bank account. Hourly employees log their time on a regular basis and receive the same.

But what about your 1099 contractors? Payroll becomes a lot more complicated when they’re completing project-based work or vary their hours month to month. Accounting teams have to cobble together legacy systems designed for traditional forms of work. This makes for a time-consuming headache for the team to sort through instead of taking care of more strategic priorities.

For businesses that rely on hundreds or thousands of contractors to do business—like healthcare company Teledoc, which employs a network of independent 10,000 healthcare providers; Pacesetter, an insurance services company built on independent claims adjusters, or Superpath, a small-but-mighty marketing agency—this isn’t just a headache. An inefficient payroll process slows down growth and creates operational backups that ripple across the organization.

Scaling contractor payments to 10,000 contractors

For Teladoc Health (NYSE: TDOC), the global leader in virtual care, their vast network of nearly 10,000 healthcare providers meant a broken payroll system kept their team drowning in manual processes and reconciliation requests. They needed a system designed to handle a high volume of payouts that gave both their finance team and their healthcare providers peace of mind.

“Providers had no visibility into their earnings-they only saw a lump sum deposited into their account,” said Tricia McGimpsey, VP Payroll. “It was creating an enormous amount of manual work for the payroll department.”

Teladoc needed a solution that could streamline payments while offering a self-service experience for providers. Wingspan created a unified self-service provider portal that gave providers full visibility and control over their payment experience to update information, track payments, and access their tax documents independently. This integrated directly with Teladoc’s consult system to match action with invoice.

Doing this saved 28 hours per month for Tricia’s team—and over $230,000 in IT and accounting expenses. “You gave me back 14 hours of my life each cycle,” Tricia said. “It used to take me two days to process payroll. It takes me two hours to process payroll from start to end.”

Paying contractors faster and more reliably boosted business

Like Teladoc, Pacesetter’s large network of 3,000 insurance adjusters spread across the country meant payroll needed extra steps and workarounds to accommodate 1099 requirements. This slowed down their process—and with plenty of competition with other claims firms for contractor talent, CEO Bill Brassfield wanted to be the company contractors wanted to work for.

“Our contractors drive most of our organization’s revenue, and they’re the backbone of the insurance industry,” said Brassfield. “We want to keep them happy by offering a high-quality payment experience, one that sets a new standard for how our industry treats 1099 workers.”

In addition to a smoother payroll system, Wingspan gave Pacesetter the ability to offer its adjusters access to a range of health and financial benefits, typically reserved for full-time W-2 employees, that included:

• Financial management assistance, including tax management, bookkeeping, invoicing, and banking features
• Medical, dental, vision, and disability benefits
• Access to Wingspan’s support team for advice on tax, accounting, and benefit issues

Not only did Wingspan’s new payroll system reduce payment errors by 40%, it also created a contractor-friendly experience that differentiated them in the market, boosting retention.

“Wingspan was the only platform that allows us to pay our adjusters faster and more conveniently while also providing them with access to health and financial benefits,” said Brassfield.

A seamless payout process that eliminates support tickets

Entrepreneur and Superpath CEO Jimmy Daly didn’t have time to fuss with the kind of manual payroll processes you have to fiddle with for his network of contractors. As a fledgling marketing agency for high-growth startups, Daly was scrambling to keep up with demand. 

“I was constantly worried about whether my payroll information was incorrect, which would be serious in the case of an audit,” said Daly. I want to attract great freelance writers and keep them. A big part of that is paying them on time.”

Wingspan immediately automated the payroll process, saving 30 hours a month in the invoicing process and reducing back-and-forth emails from his freelance team by 90%. Instead of doing admin work, Daly can spend time directly with clients—and continue to build his business. “In May, I was spending countless hours managing payroll and fielding questions from my writers,” said Daly. “By July, Wingspan was fully operational. Wingspan makes the most critical part of our business, paying writers on time, seamless. It’s easily the most important tool in our tech stack.”

Why these businesses choose Wingspan

We built Wingspan with contractors in mind. Instead of manual payments juggling multiple systems (or worse, a spreadsheet!), you can automate the entire process. From onboarding a new contractor to handling 1099 forms come tax time, Wingspan can help you completely manage the contractor lifecycle. 

“The Wingspan system is incredibly seamless,” said Tricia. “It has completely transformed the way Teladoc manages 1099 Provider Payroll. Highly recommend Wingspan for any company looking to streamline their operations, boost productivity and increase provider satisfaction!” 

With Wingspan, you get:

1. Automation: Eliminate manual payment processes like adding funds or notifying your contractors about payment. With Wingspan, you can create recurring invoices that automatically go into your system each month so your contractors get paid without having to go back-and-forth.

2. Standardization: Every contractor can fill out the same paperwork where both parties can see it securely, from W9s, ACH forms, and any other onboarding information your team needs to get them working as soon as possible.

3. Self-service: Wingspan combines the best of both worlds, with a powerful API and an ability to embed Wingspan's admin console, allowing non-technical users to manage all aspects of contractor management, plus dedicated support teams to help you and your contractors if any issues arise.

Said Bill, “Wingspan is a must-have software for any claims business that depends on contractors.”   

Manage the entire contractor lifecycle with Wingspan. Learn more >