The W-9 Chase That Consumes Your Tax Season
It starts innocently enough. You send an email requesting a W-9 from a new contractor. Then another. And another. No response. The contractor claims they never received it. Or they send an incomplete form with a missing tax ID. Or the address is wrong. Now you're following up again, and the January 31 deadline is approaching fast.
This is the reality for finance teams managing contractors: Manually chasing contractors for W-9s is time-consuming and frustrating. Payroll and AP teams waste hours following up on missing or incorrect forms, causing stress during tax season and risking filing delays.
One accounts payable manager told us: '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.'
A week. For a single part of the 1099 process. Multiply that across hundreds or thousands of contractors, and you've got a full-time job just collecting forms: before you've even started the actual filing process.
The Last-Minute TIN Scramble
But the W-9 chase is only the beginning. The real nightmare hits when you discover incorrect tax IDs late in the process.
Picture this: It's January 20th. You're 11 days from the IRS deadline. You've finally collected all the W-9s and you're ready to file. Then you run TIN verification and discover that 15% of your tax IDs are invalid or don't match IRS records.
Discovering incorrect tax IDs late in the process creates emergency situations. Now you're scrambling to:
• Contact contractors urgently to get corrected information • Re-verify new tax IDs with the IRS TIN matching program • Update your records and regenerate 1099 forms • Hope you can still meet the January 31 deadline • Deal with stressed contractors who don't understand why this is urgent
And if you don't catch these errors? The IRS charges penalties up to $330 per form for incorrect information. With hundreds of contractors, that exposure adds up fast.
The cruel irony? All of this could have been prevented months earlier with automated validation during onboarding.
The Support Ticket Avalanche
Even if you successfully collect W-9s and validate TINs, there's a third pain point waiting: the January support ticket avalanche.
As soon as contractors need their 1099s, your inbox explodes:
• 'Where's my 1099?' • 'Why does this amount look wrong?' • 'Can you resend that?' • 'How do I download this?' • 'I need a correction: who do I contact?'
Repeatedly answering the same questions from contractors about payment calculations, timing, and tax implications drains time and energy. AP and Finance teams get bombarded with emails and calls during tax season, pulling them away from critical filing work and creating frustration on both sides.
One telehealth company managing 10,000+ providers told us they used to handle 'thousands of emails from providers about their 1099 forms' every tax season. Their accounts payable manager spent half her time in January just sending: and fixing: 1099s to contractors.
This isn't a tax compliance problem. It's a contractor experience problem that creates operational chaos.
How Automation Eliminates All Three Pain Points
Companies that switch to Wingspan before tax season eliminate these pain points entirely. Here's how:
Pain Point 1: Manual W-9 Collection Solution: Automated Digital W-9 Collection
Wingspan's digital onboarding flow automatically requests W-9s from contractors when they join your network. The form is built into the onboarding process: contractors can't proceed without completing it. No manual follow-ups. No missing information. No incomplete forms.
'We know tax season brings extra stress, especially when collecting and validating contractor W-9s,' says one finance leader. 'Wingspan automates this process, ensuring all forms are submitted correctly through a digital onboarding flow: no more manual follow-ups or missing information.'
Pain Point 2: Last-Minute TIN Validation Errors Solution: Real-Time TIN Verification with IRS Integration
As contractors complete their W-9s, Wingspan immediately cross-checks their tax IDs with the IRS database. If verification fails, the system triggers an instant notification prompting the contractor to re-enter accurate information: right then, during onboarding, months before you need to file.
'With Wingspan's real-time TIN matching and IRS integration, you'll catch issues early: well before they become problems,' explains the platform's approach.
No January scrambles. No emergency situations. No penalties. Just confidence.
Pain Point 3: Support Ticket Avalanche Solution: Contractor Self-Service Portal
Wingspan's contractor portal gives contractors 24/7 access to:
• Instant 1099 downloads on January 31 • Detailed payment breakdowns showing exactly what's reported • Direct correction request workflows • Help resources and FAQs • Real-time status updates
The result? The telehealth company that used to handle 'thousands of emails' now reports a 90% reduction in contractor support tickets. 'We don't need all-hands on deck anymore now that we've got Wingspan,' their AP manager says.
Why November Is Your Implementation Window
Here's the critical insight most companies miss: You can't fix these problems in January. By then, you're in crisis mode, racing toward the deadline.
The companies that have seamless tax seasons implement their automation in November. Here's why that timeline matters:
November: Setup & Migration (Weeks 1-4) • Automated W-9 collection begins for all existing contractors • Real-time TIN verification catches and corrects errors immediately • Historical payment data syncs with accounting systems • Contractor portal setup provides self-service access
December: Testing & Training (Weeks 5-8) • Contractors learn to access payment history and tax documents • Your team tests correction workflows and approval processes • Integration with QuickBooks or other platforms is confirmed • Any issues are identified and resolved: with time to spare
January: Seamless Filing (Weeks 9-12) • 1-click filing automatically generates, reconciles, and files 1099s • Contractors download forms instantly on January 31: no delays • Support tickets drop by 90% because contractors self-serve • Your team focuses on strategic work, not support chaos
Companies that wait until December or January miss this implementation window and end up implementing under deadline pressure: exactly when you can't afford mistakes.
Your Limited-Time Advantage
Switch to Wingspan before Nov. 30 and get a free premium dedicated support package for your first tax season:
✓ Priority support for your contractors during tax season: reducing your team's burden when it matters most ✓ ✓Personalized guided onboarding for smooth 1099 migration: expert help ensuring you're ready before January ✓ ✓Dedicated implementation team with deep compliance expertise guiding your transition
This isn't just software: it's expert guidance ensuring your transition is seamless and your January is stress-free.
Companies that take advantage of this offer get:
• Automated W-9 collection that eliminates manual follow-ups and missing information
• Real-time TIN verification that prevents last-minute scrambles for corrected tax IDs
• Contractor self-service portal that reduces support tickets by 90%
• 1-click filing that generates, reconciles, and files 1099s with IRS and states
• Audit-ready compliance with detailed logs and automatic tax law updates • Integrated workflows that sync with QuickBooks, NetSuite, and other platforms
But this offer expires November 30. After that, you're implementing under deadline pressure instead of getting ahead of it.
The Real Cost of Waiting
Every day you delay automating your 1099 process is another day of:
• Manually chasing contractors for W-9s and missing information
• Risking last-minute TIN validation errors that create emergency situations
• Preparing for the January support ticket avalanche
• Working overtime to meet IRS deadlines
• Exposing your company to penalties up to $330 per incorrect form
Meanwhile, your contractors are frustrated by the manual experience, comparing you unfavorably to companies that offer seamless self-service.
'I've been in AP for over 10 years and filing 1099 forms for a long time, Wingspan is by far the easiest process I've ever come across,' says an accounts payable manager at a fast-growing telehealth startup.
The companies that get this right don't just survive tax season: they use it as a competitive advantage. While competitors scramble with manual processes and frustrated contractors, they're delivering seamless experiences that build contractor loyalty.
Don't let another tax season become a support nightmare. Get ahead now.
Stop chasing W-9s and discovering invalid tax IDs in January.
.png)
