The Hidden Compliance Crisis Inside Contingent Workforce Payroll with Anita Milasinovic

Today’s workforce looks nothing like it did a decade ago. Contingent workers, contractors, freelancers, and cross-border talent now make up a growing share of global teams, and payroll is right at the center of the risk.

In this episode of The Payroll Podcast, Nick Day is joined by Anita Milašinović from Papaya Global to unpack why contingent workforce payroll is becoming the biggest compliance challenge of our time. Together, they explore how misclassification risk, fragmented systems, unclear engagement models, and fast-changing global regulations are putting pressure on payroll teams worldwide.

The conversation breaks down why spreadsheets and disconnected processes no longer work at scale, how payroll leaders can step into a more strategic role across HR, finance, and procurement, and where AI can support compliance without replacing human judgment. Anita also shares practical insights on building consistent compliance frameworks, educating managers, and preparing for tighter enforcement across global markets.

If you work in payroll, HR, finance, or workforce strategy, this episode offers a clear look at what is changing, where the real risks sit, and how payroll can lead the way in managing a compliant, blended global workforce.

Papaya Global Workforce AI & CWX: https://www.papayaglobal.com/embedded-ai/

Data Validation / Compliance Automation: https://www.papayaglobal.com/data-validation/

Anita Milasinovic on LinkedIn: https://www.linkedin.com/in/anitamilasinovic

Nick Day’s LinkedIn: https://www.linkedin.com/in/nickday/

Find your ideal candidate with our job vacancy system: https://jgarecruitment.ck.page/691ee4537e

(00:00) The Contingent Workforce Compliance Challenge

(02:16) Payroll, Trust, and Paying People Right

(03:24) Why Contingent and Global Work Is Growing

(05:21) Talent Shortage vs Cost Pressure

(06:40) Why Spreadsheets Fail at Scale

(09:44) Common Payroll Compliance Mistakes

(12:39) Aligning Payroll, HR, and Finance

(14:30) Misclassification Risk Explained

(16:42) What CFOs Worry About Most

(18:22) Navigating Global Workforce Compliance

(20:51) AI’s Role in Payroll Compliance

(23:14) Where Human Judgment Matters

(25:07) Payroll’s Role in Blended Workforces

(28:02) Preparing for Global Enforcement

(31:54) How Providers Reduce Compliance Risk

(33:40) Advice for First Global Hires

(36:23) Lessons From Regulatory Change

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