Pain Point #1: The January W-9 Chase
The Problem: Every January, finance teams send dozens of follow-up emails begging contractors to submit their W-9s. Some forms come back incomplete. Others have incorrect information. A few contractors never respond at all. Your team wastes hours: sometimes days: on manual follow-ups while the IRS deadline gets closer. One finance leader told us their employee spends half her time in January just sending and fixing 1099s to contractors. The Impact: Manual W-9 collection is time-consuming and frustrating for payroll and AP teams, causing stress during tax season and risking filing delays. Missing or incomplete forms can trigger IRS penalties up to $660 per form. The Solution: Wingspan's automated digital onboarding collects W-9s upfront through a streamlined workflow. Contractors complete forms electronically with built-in validation that catches errors in real-time. No more manual follow-ups. No more missing information. No more January scrambles.
Pain Point #2: Last-Minute TIN Verification Emergencies
The Problem: It's January 20th. You're preparing to file when you discover that multiple contractor tax IDs don't match IRS records. Now you're in emergency mode: frantically contacting contractors, waiting for corrected information, and racing against the deadline. "Discovering incorrect tax IDs at the last minute can turn tax season into a scramble," as one finance professional described it. The Impact: Finance teams face last-minute scrambles to correct information, risking penalties and having to file corrections after the deadline. Each incorrect TIN can result in penalties, and corrections require additional work and IRS resubmission. The Solution: Wingspan's real-time TIN matching integration verifies tax IDs with the IRS database during contractor onboarding: well before tax season arrives. If verification fails, the system immediately triggers a notification prompting the contractor to re-enter accurate information. You walk into January knowing every tax ID is IRS-validated.
Pain Point #3: Payment Threshold Tracking Across Multiple Systems
The Problem: Manually tracking which contractors meet the $600 filing threshold when payments are scattered across multiple systems is error-prone and time-consuming. You're reconciling ACH payments, paper checks, expense reimbursements, and credit card transactions: all from different sources. The Impact: AP teams must manually reconcile payments across systems, risking missing contractors who should receive 1099s or unnecessarily filing for those who shouldn't. This increases the risk of both under-reporting (IRS penalties) and over-reporting (contractor complaints). The Solution: Wingspan automatically tracks all contractor payments throughout the year, regardless of payment method. The system maintains a running total and automatically flags contractors who cross the $600 threshold, ensuring accurate filing without manual tracking.
Pain Point #4: State Filing Requirement Complexity
The Problem: Keeping track of different state filing deadlines, formats, and thresholds is overwhelming. Each state has unique requirements, and staying current with changes requires constant research and monitoring. The Impact: Tax professionals spend excessive time researching requirements and risk missing state deadlines, which can trigger additional penalties beyond federal IRS fines. The Solution: Wingspan automatically handles state-specific filing requirements, tracking deadlines and formats for all states where you have contractors. The platform updates automatically when state regulations change, ensuring compliance without manual research or monitoring.
Pain Point #5: Year-End Data Consolidation Marathon
The Problem: Aggregating payment data from multiple sources: ACH, checks, expense reimbursements, credit cards: is tedious and error-prone. Finance teams spend weeks at year-end reconciling payments, often working overtime to meet deadlines. "Year-end data consolidation shouldn't take weeks," yet for many teams, it does. The Impact: Finance teams spend weeks at year-end reconciling payments, often working overtime to meet deadlines. This manual process pulls them away from strategic work and increases the risk of calculation errors that can lead to incorrect 1099 amounts. The Solution: Wingspan automatically consolidates payment data from all sources throughout the year. The platform integrates with your accounting systems and payment platforms, maintaining a single source of truth. When January arrives, your 1099s are ready to generate in one click: no reconciliation needed.
Pain Point #6: Filing Corrections and Error Management
The Problem: Discovering errors after filing means going through the manual correction process: preparing corrected forms, tracking which contractors received corrections, and resubmitting to the IRS. Each correction requires documentation and follow-up. The Impact: Accounting teams must drop other work to handle corrections, damaging their reputation with management and causing stress. Corrections also risk additional scrutiny from the IRS and can delay contractor tax filings. The Solution: Wingspan's built-in correction workflows make fixes quick and hassle-free. Contractors can request corrections through the self-service portal, and the system handles automated notifications and IRS resubmission with complete audit trail documentation.
Pain Point #7: The Contractor Support Ticket Flood
The Problem: January brings a flood of contractor questions that disrupts your team's workflow. "Where's my 1099?" "Why does this amount look wrong?" "How do I download this?" "Can you send it again?" One telehealth company told us they used to handle thousands of emails from providers about their 1099 forms each tax season. The Impact: 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. This support burden can consume as much time as the actual filing process. The Solution: Wingspan's contractor self-service portal eliminates 90% of support requests. Contractors can download their 1099s instantly, view detailed payment breakdowns, and request corrections directly: all without contacting your team. Companies using Wingspan report cutting contractor support tickets in half.
Your Strategic Window: Get Ahead Before January
Here's what makes October the perfect time to fix these pain points: You have bandwidth to implement solutions properly instead of rushing under deadline pressure. You can onboard contractors into new systems before tax season, so they're familiar with self-service portals when January arrives. You have time to validate W-9s, verify TINs, and correct errors before they become filing emergencies. You can test integrations and ensure everything works smoothly without the stress of an IRS deadline looming. Right now, Wingspan is offering a limited-time opportunity: Switch before Nov. 30 and get a free premium dedicated support package for your first tax season: priority support for your contractors and personalized guided onboarding for a smooth 1099 migration. This isn't just software. It's a complete solution with hands-on support to ensure you eliminate every pain point before January arrives.
What Your Pain-Free January Looks Like
When you automate these pain points before tax season, here's what January actually feels like: No W-9 Chasing: All forms were collected and verified during onboarding: months ago. No TIN Emergencies: Every tax ID was validated in real-time with the IRS: no last-minute corrections needed. No Data Consolidation: Payment tracking happened automatically all year: no manual reconciliation required. No State Filing Confusion: Wingspan handles all state-specific requirements automatically: no research needed. No Correction Chaos: Built-in workflows handle any changes smoothly: no manual IRS resubmission stress. No Support Floods: Contractors use self-service portal: your inbox stays manageable. No Overtime: Your team files 1000+ 1099s in hours: no nights and weekends required. This is what getting ahead looks like. This is what eliminating pain points before tax season delivers.
Ready to eliminate the manual work that makes tax season a burden?
Switch to Wingspan before Nov. 30 and get premium support free for your entire first tax season. →
.png)