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2026 Predictions: What the Gig Economy Means for Finance, Compliance & Ops Teams

The contractor workforce isn’t slowing down - scrutiny is rising, and internal expectations are rising even faster. Join Wingspan for a forward-looking conversation on what’s changing in 2026 and how finance, compliance, and ops teams can stay ahead.

In this session, we’ll cover:

  • How flexible work models are evolving in 2026, and what that means operationally
  • What regulatory, compliance, and worker classification scrutiny looks like this year
  • How finance and ops teams are being asked to do more with contractor-heavy workforces
  • Why legacy AP and payroll systems are showing cracks (and where teams feel it first)

More businesses are relying on flexible labor, but finance, compliance, and ops teams are absorbing the complexity. This webinar is designed to help you anticipate what’s next and leave with practical ways to prepare, without adding more manual work to your team.

This webinar is for you if you’re responsible for:

  • Contractor onboarding, W-9 collection, and tax workflows
  • Worker classification risk and audit readiness
  • Payment operations for 1099s (at scale, across teams/systems)
  • Reducing manual workload, support tickets, and “spreadsheet compliance”

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Greg Franczyk
Greg Franczyk
Co-Founder & CTO, Wingspan
Kerri Florian
Kerri Florian
Director of Accounting, Wingspan
Understand what’s coming and how to prepare
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Greg Franczyk
Greg Franczyk
Co-Founder & CTO, Wingspan

With over a decade of experience leading engineering teams at companies like Google and The Washington Post, Greg Franczyk understands how scalable systems break—and how to rebuild them. He’ll use that lens to unpack what finance and ops teams should expect as flexible work continues to reshape processes in 2026.

Kerri Florian
Kerri Florian
Director of Accounting, Wingspan

As a senior accounting leader who has guided finance teams through the intricacies of 1099 filing, contractor onboarding, and compliance workflows at scale, Kerri Florian offers hands-on insight into what works, and what doesn’t, when managing flexible workforces. In this session, she’ll share actionable strategies to help your team stay efficient, accurate, and audit-ready as the gig economy continues to expand.

Trusted by businesses that run on contingent work