The Hidden Cost of Scaling Contractor Networks
Year-end data consolidation shouldn't take weeks. But for companies managing hundreds or thousands of contractors across multiple payment systems, December becomes consumed by manual work. Finance teams aggregate payment data from ACH transfers, paper checks, expense reimbursements: often working overtime to meet the January 31st deadline. One finance and operations leader told us they have an employee who spends half of her time in January sending and fixing 1099s to contractors. This is valuable time that could be spent on year-end close and financial reporting. The scaling challenge: What works for 50 contractors breaks at 500. Manual spreadsheets become unmanageable. Tracking which contractors meet the $600 filing threshold across multiple payment systems becomes error-prone, risking missing contractors who should receive 1099s or unnecessarily filing for those who shouldn't.
The W-9 Collection and TIN Verification Challenge
Manually chasing contractors for W-9s and tax information 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. Then comes the emergency: Discovering incorrect or invalid tax IDs late in the process creates last-minute scrambles. Finance teams face emergency situations to correct information, risking IRS penalties and having to file corrections. With penalties ranging from $60 to $330 per form: and up to $660 for intentional disregard: the financial exposure adds up quickly when managing thousands of contractors.
How Teladoc Scaled to 10,000 Without the Burden
Teladoc Health manages nearly 10,000 healthcare providers: a scale that would overwhelm most manual processes. Their VP Payroll, Tricia McGimpsey, describes the transformation: 'It used to take me two days to process payroll. It takes me two hours to process payroll from start to end.' That's not just faster: it's fundamentally different. Wingspan automates the end-to-end 1099 filing process: Automated W-9 Collection: Digital onboarding flow ensures all forms are submitted correctly: no more manual follow-ups or missing information. Real-Time TIN Verification: Instant cross-checking with IRS database catches incorrect tax IDs during onboarding: well before filing deadline pressure. Automatic Payment Tracking: Every contractor payment captured automatically across all sources: no year-end reconciliation scramble. 1-Click Filing: System automatically generates, reconciles, and files 1099s with IRS and states. The results? Teladoc saved 28 hours per month and over $230,000 in IT and accounting expenses.
Why State Filing Requirements Multiply the Complexity
Keeping track of different state filing deadlines, formats, and thresholds is overwhelming. Tax professionals spend excessive time researching requirements and risk missing state deadlines. Each state has unique rules: some require filing for amounts lower than the federal $600 threshold. Some have different deadlines. Some require different forms. The manual approach breaks down: When you're managing contractors across 10, 20, or 50 states, tracking these variations becomes impossible without automation. Wingspan handles all state requirements automatically: tracking deadlines, managing formats, and ensuring compliance across every jurisdiction where your contractors work.
The November Advantage: Get Ahead of Tax Season
Here's what most companies miss: Timing matters. Companies that switch to Wingspan before tax season avoid implementing during peak filing pressure. You'll have time to: Complete digital W-9 collection for all existing contractors, verify all TINs with real-time IRS matching, import and consolidate historical payment data from all sources, train your team on automated workflows before deadline stress, onboard contractors to self-service portal so they're ready in January. Wait until December or January? You'll be implementing while racing to meet filing deadlines: exactly when you can't afford disruption or learning curves. Switch to Wingspan before Nov. 30 and get more than software: Unlock 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.
The Premium Support Advantage
What makes Wingspan's premium support package different? It's designed specifically for companies scaling through their first tax season with automated 1099 filing: Priority Contractor Support: Your contractors get dedicated assistance during peak filing season: reducing your internal support burden when ticket volume typically increases. One telehealth company told us they used to handle 'thousands of emails from providers about their 1099 forms' each tax season. Wingspan's contractor help desk handles common queries, providing real-time updates and in-app corrections. Personalized Guided Onboarding: Expert implementation ensures your W-9 data is collected, your TINs are verified, your payment data is consolidated, and your team is confident: all before January filing deadlines hit. Tax Season Readiness: We don't just set up software: we eliminate the pain points that burden scaling companies during tax season.
Ready to scale without year-end burden? Switch before Nov. 30 and get premium support for seamless January filing →
