For accounting teams, the January deadline for 1099-NEC filing is the Super Bowl. Okay, maybe there aren’t 127 million people around the world watching finance and accounting teams perform TIN matching manually, but the pressure is real! After all, there are potential IRS penalties for each information return not provided on time.
Let’s outline some of the major challenges to filing 1099-NECs by the deadline, and how to solve them.
The Challenge: Disjointed Processes and Data Accuracy Issues
When you don’t have one source of truth for 1099 completion or verification, it’s easy for errors to slip through the cracks. But that’s bound to happen when you have one vendor for payment processing, another for W-9 collection, and yet another for background checks.
And what if there’s data about a contractor’s updated legal name or address change buried in an email chain? Or incorrect information in a W-9? Mistakes are bound to happen. If there’s an inconsistency between your records and what’s reported to the IRS, and it’s not fixed by August 1, that’s a penalty of $330 per statement.
The Solution: Verification, W-9 Collection, and Payment Processing... All In One Place
When you onboard a contractor through Wingspan, payment processing, W-9 collection and background checks are all done in real-time by our system. Those manual processes you’re used to? Gone. The promotional tasting company Pourtastic found serious time savings streamlining their manually-intensive back office with Wingspan, with 30+ hours saved monthly by automating manual onboarding, payment, approval processes.
And try to imagine this: you’ll never have to send an email to collect W-9 info again. Doesn’t that feel nice? Wingspan’s platform automates requesting a W-9 and then cross-checks their TINs with the IRS – that means fewer errors from day 1. If the verification fails, an automated notification asks the contractor to send an accurate TIN. It’s just one way Wingspan automates what was once a slog of a manual process.
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The Challenge: Manually Driven Workflows
In a world where AI can create a realistic looking video in seconds, why are we still processing 1099-NECs manually? But that’s the reality in 2025, and it can seriously sap the resources of even the most efficient finance team. There is a better use of your team’s time than tracking TIN changes or communicating with contractors. But when it has to get done by January 31st, it’s all hands on deck. Unless, of course, you automate the process.
The Solution: Automate, Automate, Automate
When you offload your 1099 processing to Wingspan, you transform a costly, burdensome and time consuming process into one that just gets done. For example, when contractors have questions, Wingspan has answers. Finance teams often spend hours answering basic questions over email like:
- Can you change the address on my 1099-NEC?
- When will I receive a copy of my 1099-NEC?
- Can I update my TIN?
- How can I see which payments were included on my 1099-NEC?
When you choose Wingspan to handle your 1099 processing, we can answer those questions easily and quickly. Not only that, our intuitive self-service portal gives contractors a place to download their 1099-NEC forms and check their payment amounts. Imagine what your team could do with an extra 20+ hours a month not answering questions from contractors. You know what? No need to imagine, read about how the good folks at Pourtastic saw those savings for themselves.
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The Challenge: The High Cost of Outsourcing
Even if your finance team is no longer running the 1099 process manually, you could be outsourcing it to multiple companies in order to ensure compliance. There are costs to that convenience – financial leaders we’ve spoken to say they can spend upwards of $30,000 annually for vendors to assist with 1099 processing. Add to that process W2 payroll software or billpay tools that often have incomplete information, and odds are that your team is still having to spend time and resources every January to get 1099 filing done on time.
The Solution: A Platform Purpose-Built for 1099s
Global virtual care leader Teladoc uses Wingspan to streamline their payments and offer a self-service experience for their providers, and it helped them save $230,000 in IT and accounting resources. The transformational results didn’t end there – read Teladoc’s full story here.
Wingspan’s purpose-built tooling offers a single platform that automates the full contingent work lifecycle, making it easy to bill clients, onboard and pay contractors, and file 1099s. The days of paying multiple vendors to get a fraction of the work done are over. To learn more about how to offload your 1099 processing to Wingspan, get in touch by requesting a demo.
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