The Great Platform Shift
Rethinking 1099-K & NEC Strategy for B2B Gig Compliance in 2025
Speaker
Jeffery Cronin
(Chief Strategy Officer, Zenwork)
Webinar Date
10th July 2025
Time
1 pm CT
Duration
45 Mins
Agenda
1. Welcome to 2025: The Compliance Crossroads
- 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 Mid-Year Trigger: $2,500 Threshold Goes Live
- a. What the new 1099-K threshold really means for your users and reporting burden
- b. How it’s reshaping B2B platform strategies and tax workflows
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. clients file
4. Hidden Risks of Misreporting
- a. IRS mismatches, B-Notices, state-level scrutiny
- b. How simple reporting 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. Preparing for the $600 Era: A Futureproof Plan
- a. Why the 2025 shift is just a dress rehearsal
- b. IRS AI, Form 1099 automation, and what’s next
- c. Portals, APIs, and building an enterprise-grade compliance stack
8. Bonus Toolkit: Leave With a Playbook
- a. Downloadable 2025 NEC vs. K strategy guide
- b. Multi-state reconciliation calendar for your tax team
Description:
The 2025 tax season marks a seismic shift for gig and B2B platform compliance. With the IRS enforcing a new $2,500 threshold for Form 1099-K midway through the year, platforms must urgently reevaluate their NEC vs. K filing strategies—or risk costly penalties and audit exposure.
In this high-impact session, we break down what the new rules mean for your platform, your payees, and your filing workflows. You’ll learn how the mid-year threshold change affects platform models (direct pay, escrow, hybrid), when to file 1099-K vs. 1099-NEC, and how to avoid classification missteps that trigger IRS scrutiny.
We’ll walk you through a decision framework for determining payer vs. PSE responsibilities, showcase how top platforms have scaled compliance with automation, and preview what it takes to stay ahead of the 2026 drop to the $600 threshold.
Whether you’re leading tax ops, product, or compliance at a growing platform, this session gives you the strategy and tools to stay ahead of regulation—and build workflows that scale.
© 2025, Zenwork. All rights reserved.