Los York Scaled to 150 Contractor Invoices a Week Without Adding Headcount

Overview

Los York is a creative production and post-production company that has grown every year since it was founded in 2012. The company runs a contractor pool that can swing from 20 people in a slow week to more than 150 in a busy one, depending on what’s in production. That swing is what Los York needed a payments platform to handle. Melissa Redondo, Chief Financial Officer at Los York, has been with the company since 2020 and is, in her own words, "kind of a one-person department."

Contractors move through the company every week, invoice for their work, and get paid on a net-30 basis. Keeping that process accurate and on schedule used to be most of what Melissa's job was. With Wingspan handling it, she has room for the rest of her work.

Challenge

Before Wingspan, contractors sent their invoices to a shared accounting inbox as PDFs, in whatever format they happened to use. Melissa had to open every one and manually key it into QuickBooks. "Back then we weren't as big as we are now," she says. "Having to do what we did manually four or five years ago now would just not be possible."

As Los York grew, the manual process stopped scaling. Payments went out as printed checks that needed a physical signature, with no central place to track which checks were even in motion. Contractors regularly asked to be paid by bank transfer, which the company couldn't offer. Nothing stopped a contractor from writing their own due date on an invoice, a habit that ran straight against the company's cash flow.

The 1099 filing season was its own kind of dread. "When January came around, I had to issue 1099s. I wanted to cry," Melissa says.

Solution

Melissa found Wingspan the way a lot of small finance teams find their tools: an ad showed up in her Instagram feed. "I was like, what is this payable company that does it all for you?" she says. She clicked through, took the product tour, and saw a platform that could take invoicing fully online.

Los York was one of Wingspan's early customers, and the relationship worked more like a build partnership than a standard rollout. Melissa needed an approval structure that matched how she actually managed risk: a producer or accounting admin could pre-approve an invoice, but final sign-off before money moved had to stay with her. "I don't want to give that approval process to somebody working on my team," she says. "I want to have the final review, because they're not aware of how it implicates the cash flow for the company." Wingspan built the two-stage approval process around that logic, working through the details with her rather than treating it as a one-off request. The same collaboration shaped the rest of how invoicing worked: contractors had been setting their own due dates, which ran against Los York's cash flow, and submitting invoices in whatever format they used, which slowed down processing at scale. Together, Melissa and Wingspan replaced both with enforced net payment terms and an invoice format she controls. "Wingspan has been very open to any request I've had," Melissa says. All three, the approval structure, the payment terms, and the format requirement, are now standard on every Wingspan account that invoices contractors, not just Los York's.

Impact

A Manageable, Scalable Contractor Roster

Los York couldn't make that swing on its own before Wingspan. Expanding to 150 contractors in a busy week, then pulling back to 20 the next, wasn't something the old manual process could handle. Now Los York expands and contracts its roster on a weekly basis, absorbed by an accounting team that's still just Melissa and one admin. "If we were still doing things the way we did, there's no way we would be able to process 50 to 150 invoices every single week," Melissa says. "There's just no stopping the amount of contractors we continue to engage."

Onboarding Runs Smoothly

Before Wingspan, bringing on a new contractor meant the talent team manually sending out Los York's NDA and independent contractor agreement, waiting for a signed copy back, and filing it in a shared drive. Wingspan now handles that through e-signature: contractors sign both documents directly on the platform, and Wingspan stores and organizes them automatically as part of onboarding. The team that used to manage that process by hand noticed immediately. "They were just like, are you kidding me? Like we don't have to do that anymore," Melissa says.

QuickBooks Syncs Itself

What used to be an Excel export and a manual upload is now automatic. Invoices flow from Wingspan into QuickBooks within about five minutes of submission, already coded to the right category because Wingspan is set up to tag each contractor correctly from the start. "The ability to not even have to think about it is even better," Melissa says. Her talent coordinators are trained on the setup steps so every new contractor flows through cleanly from day one.

1099 Season Became Automated

The process that used to cost Melissa a week of dreaded manual work every January now barely registers. Wingspan starts notifying her months in advance if anything needs attention, usually a missing address or a minor setup issue. The actual filing takes almost no effort on her end. "It's almost scary. I don't even need to think about it. Wingspan does everything," she says. "I barely have to press accept, and that's it."

Contractors Have Full Visibility

Contractors can now see exactly where their invoice sits in the payment process, and pull up their own 1099s without asking Melissa for help. "Nobody asks me these questions anymore," she says, whether it's about payment status or a missing tax form. That was a real shift from before, when paper checks and mailed 1099s meant a steady stream of pings asking where things stood.

A Way to Offer Contractor Benefits

Freelance work comes with real trade-offs, and Melissa sees Wingspan's contractor benefits, including the option to have taxes withheld directly from a payment, as a way to give some of that back to Los York's contractors. "To be able to offer some sort of full-time benefits through the Wingspan platform is something that is special for us to be able to offer to our contractors," she says.

Looking Forward

Los York is exploring Wingspan's new support for seasonal, part-time, and temporary W-2 workers. The company is fully remote and hires flexible W-2 employees in multiple states, a process that currently runs through a separate payroll provider and can cost Melissa close to a full day per state just to register for the right business licenses and unemployment insurance. Bringing that group onto Wingspan alongside its 1099 contractors is a conversation the two teams have just started.

Los York has also started working with much larger production partners, and the data security expectations that come with that shift are on Melissa's mind. Background checks and identity verification are available in Wingspan but not yet turned on for Los York's contractors. "I don't utilize it as much as I should," she says, "but I'm just so happy that it's there if I need it."

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