cartoon gunslinger cowboys facing each other The notion of employees working all over the country or around the world could create a Wild West scenario for HR when it comes to tax compliance. (Photo: Shutterstock)

Airbnb CEO Brian Chesky made headlines recently when he announced he’d be spending the next year moving from city to city every two weeks living and working in Airbnb properties. This sounds like a digital nomad’s dream, and technically it’s entirely feasible. But the first thing that came to mind is, “I wonder if HR is freaking out? This could be a compliance nightmare if they’re not prepared.”

While living in a new city every two weeks probably isn’t a realistic scenario for many employees, it underscores the possibilities that remote work affords. Employees have made it abundantly clear that flexibility to work anywhere they choose is a top priority. And as long as they’re remaining productive and engaged, employers have little choice but to extend the opportunity—otherwise they risk losing great talent.

Complete your profile to continue reading and get FREE access to, part of your ALM digital membership.

Your access to unlimited content isn’t changing.
Once you are an ALM digital member, you’ll receive:

  • Critical information including cutting edge post-reform success strategies, access to educational webcasts and videos, resources from industry leaders, and informative Newsletters.
  • Exclusive discounts on ALM, BenefitsPRO magazine and events.
  • Access to other award-winning ALM websites including and

Already have an account?



Join BenefitsPRO

Don’t miss crucial news and insights you need to navigate the shifting employee benefits industry. Join now!

  • Unlimited access to - your roadmap to thriving in a disrupted environment
  • Access to other award-winning ALM websites including and
  • Exclusive discounts on and ALM events.

Already have an account? Sign In Now
Join BenefitsPRO

Copyright © 2023 ALM Global, LLC. All Rights Reserved.