Is Global Remote Work Testing Compliance Limits?

October 09, 2025

📝Editor’s Note

This week’s headlines remind us how fast the regulatory frame is shifting under our feet. As remote work expands, safety and labor laws across borders are catching up — compliance teams must anticipate surprises, not react to them. Are you ready for the next pivot?

Remote work has evolved from a perk to a structural necessity for many firms. But going global introduces compliance complexity. U.S. companies with employees abroad must manage immigration rules, employment rights, tax and benefits obligations, data protection, and social security impacts. 

A misstep can create unexpected exposure: for instance, an overseas worker might trigger a permanent establishment in that country, placing corporate tax burdens on the employer. Local labor laws may grant rights from day one, which cannot always be contractually waived.

To navigate this, employers should:

  • Define clear remote work policies for cross-border work

  • Monitor tax treaties and local rules

  • Use employment agreements tailored to local law

  • Collaborate closely with legal, tax, HR, and IT teams

In short: global remote work demands not just flexibility, but foresight.

✅ Best Practice Spotlight

Managing Compliance in Remote and Cross-Border Work

  1. Perform a jurisdictional risk map before approving remote or cross-border assignments

  2. Build a decision matrix for remote work approvals (duration, location, legal risk)

  3. Ensure data localization and cross-border transfer controls in remote setups

  4. Require remote employees to use secure connectivity tools (VPNs, endpoint security)

  5. Maintain audit trails of remote-work decisions, approvals, and compliance checks

  6. Regularly review and update agreements, policies, and taxation thresholds.

🛠️ Tool of the Week

OSHA Compliance Tools

These tools help U.S. companies track and manage workplace safety and regulatory compliance.

  • Many support OSHA 300 logs, incident tracking, audit prep, and reporting

  • Some have free versions or trials, though advanced features usually require subscription

  • Key selection criteria: ease of use, scalability, integration with HR systems, regulatory updates

🌟 Leader Spotlight

Enteractive is Expanding into the U.S.

Enteractive, an iGaming engagement provider, is expanding from Europe into the U.S. with a strong compliance-focused foundation. Their growth approach prioritizes precision over speed. For years, they have operated in heavily regulated European markets, building robust internal compliance, player protection, and oversight mechanisms. Now entering the U.S. market — with its patchwork of state-level gambling laws — Enteractive leans on its tech-first, compliance-anchored model. Their U.S. operations are led by Sean Phinney, who brings experience across iGaming and digital marketing. Their story shows that in regulated markets, compliance isn’t overhead—it can be a competitive strength.

🗳️ Your Compliance Take

Here are the results of our Tuesday’s poll. AI and algorithmic transparency tops this week’s poll at 26%, edging out digital assets, non-financial reporting, and privacy enforcement — clear signs of shifting priorities in compliance and tech governance.

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