Digital Transformation in Finance: Wingspan's Role in Reshaping Contractor Payments

Traditional accounts payable and payroll tools fall short when it comes to managing your contractors. They may handle payroll for your full-time employees perfectly fine, but with variable timelines, project-based fees, or internationally-based contractors, you’re stuck cobbling together multiple tools manually to get payments out the door.

Not only does this slow down the entire process, it leaves room for human error. Even the most detail-oriented finance pro can make a mistake copying-and-pasting from several tools or going back-and-forth with contractor invoices.

It’s time for something different.

Your business has likely already invested in digital transformation for key functions in accounting, sales, and support. Why require your finance team to manage contractors like it’s 1995?

Improve the speed, accuracy, and reliability of your contractor payments

The secret to a streamlined contractor payment process? Automating the manual payment processes that slow down your team’s operations so you can focus on more strategic, impact-driven tasks rather than administrative load.

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For your contractor payments to be as easy as your W2 payroll process, you need:

• Accuracy: Create a transparent process where contractors and team members can access a single source of truth on outstanding invoices, approvals, and disputes so both sides have the data they need to reconcile any issues right away.
• Speed: 84% of contractors would choose instant payments if given an option. But even if you don’t want to offer instant payouts, automation can reduce cycle times and make it easy to deliver payouts via secure ACH rather than waiting to mail a check.
• Reliability: Your W2 employees know exactly what day they’re going to get paid every single month. Do the same for your 1099 contractors by creating a predictable schedule of payouts with trusted banking partners.

To get this done, you need a payroll tool designed with contractors in mind. That’s where Wingspan comes in.

The contractor payroll process in the digital transformation era

Pourtastic Tastings founder Keith Diamond felt frustrated about the manual process he was using to get payroll done. With 750 contractors, he needed a way to get them paid quickly. “Getting payments out to our contractors is obviously critical to what we do,” he says. “If they don’t get paid, we’re done. If they don’t get paid on time, we’re in a lot of trouble.”  

He partnered with Wingspan to transform his contractor payroll—and in the process, saved more than 50 hours a month on administrative tasks and contractor support. 

Instead of toggling between several different tools, Diamond set up a more streamlined process that looks like this:

1. Add a payment method and pre-fund payroll with a corporate bank account.
2. Schedule automated payments for recurring retainers if needed. Otherwise, a contractor completes work and submits an invoice to the team.
3. Create payments and/or pay an invoice, which the contractor will receive on a scheduled date (say, the 15th of the month.)
4. Managers approve payments.
5. Contractors get paid in a timely fashion for their hard work.

With Wingspan, it all happens in one place, so you’re not juggling cost center numbers or entering data into a spreadsheet to track it. 

Automate your contractor payments with Wingspan

At the heart of Wingspan’s platform is the ability to create and manage invoices automatically. Automatic invoicing allows you to keep track of contact information, payment required, work summary, and status, approving and managing outstanding invoices at-a-glance. 

“Wingspan has saved me hundreds of hours processing invoices, running reports and responding to ambassadors,” adds Allison Bernhart, Pourtastic’s Director of Information Resources. “It’s an absolute must-have for businesses that run on contractors.”

“Wingspan has saved me hundreds of hours processing invoices, running reports and responding to ambassadors. It’s an absolute must-have for businesses that run on contractors.” - Allison Bernhart, Director of Information Resources at Pourtastic

Invoices can be sent to the client immediately, scheduled for a future date, or set to be recurring. Invoices recur monthly or weekly. Larger companies with hundreds or thousands of contractors can also bulk upload invoices, eliminating tedious data entry for each contractor individually. 

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No finance professional wants to be stuck answering tickets all day, either. With Wingspan, you can set up a self-service portal for your contractors to ask questions, edit their information, or raise any payment issues. But Wingspan’s invoicing features—including payment confirmation and automatic reminders—make it easier to communicate with a large team of contractors so you’re not constantly fielding inquiries from your part-time team. 

With Wingspan, you can:

• Automatically compute payment amounts and auto-generate contractor invoices that you can schedule ahead of time
• Pay contractors through ACH, Debit, Credit, or instant transfer
• Provide self-service support for contractors to answer their questions and deal with any issues that might come up

Says Diamond, “Wingspan helps us manage payment reliability, back office support and compliance so we can focus on growing the business.”

See how Wingspan is changing what contractor management looks like for finance teams >

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