July 29, 2025 1 - 2 PM CT
The Great Platform Shift
Rethinking 1099-K and NEC for 2025 Compliance
Organized by Zenwork Tax1099
Speaker: Jeffery Cronin (Chief Strategy Officer, Zenwork)
Webinar Date: 29th July 2025
Time: 1 pm CT
Duration: 45 Mins
Description:
With the boom in Gigfication and millions more joining platform work, finance teams face a new reality: more payees, more forms, and far more complexity. Add to IRS crackdowns, tighter 1099-K rules, and real-time audits—and the pressure is on.
In this strategic session, we break down how leading platforms are navigating NEC vs. K decisions, hybrid payout models, misclassification risks, and regulatory red flags. Learn how top GIG companies are scaling compliance with automation, smart validation, and audit-ready workflows.
Agenda
1. The Compliance Crossroads in 2025 for Big GIG Players
- a. What’s changed and why every platform is rethinking compliance now
- b. IRS enforcement trends: real-time audits, faster penalties, and tighter oversight
2. The history of 1099-K and how we got here
- a. Form source and the initial requirements
- b. Evolution of reporting under the Build Back Better Act
3. NEC vs. K: Choosing the Right Path (and Why It Matters)
- a. Direct pay, escrow, hybrid payouts—how tax treatment changes by model
- b. Real-world examples of mixed income + misclassification fallout
- c. Interactive decision tree: PSE or payer? When platforms vs. client’s file
4. Hidden Risks of Misreporting
- a. IRS mismatches, B-Notices, state-level scrutiny
- b. How to simply report errors spiral into regulatory red flags
5. From Filing Chaos to Scalable Tax Operations
- a. Automating W-9/W-8 collection and real-time TIN matching
- b. B-Notice prevention, bulk state e-filing, and smart validations
- c. Why leading platforms treat compliance like infrastructure
6. Spotlight: What Top Gig Platforms Are Getting Right
- a. Case study: 200K+ NEC filings, 99.8% accuracy
- b. Behind-the-scenes of a scalable, audit-ready compliance setup
7. Bonus Toolkit: Leave With a Playbook
- a. Downloadable 2025 NEC vs. K strategy guide
- b. Multi-state reconciliation calendar for your tax team
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