Most firms still treat international remote work as “too hard.” John Lee argues the opposite: with AI-driven risk assessments and a tight policy, Work From Anywhere (WFA) becomes a practical benefit that cuts attrition, widens your talent pool, and doesn’t blow up your risk budget. The surprising bit? Only about 4% of companies measure WFA ROI, so most are flying blind on one of the highest-leverage benefits in years.
Episode: Progressive HR Live with John Lee, CEO of Work From Anywhere
Theme: Using AI and lightweight compliance to approve cross-border work in seconds, measure ROI properly, and make mobility a retention magnet.
Highlights From the Conversation
1) Why WFA now
- Employees want limited, approved international trips alongside hybrid domestic policies. Think “up to 30 – 90 days abroad, with guardrails,” not permanent digital nomadism for everyone.
- HR leaders are balancing risk, cost, and a real retention lever. Certain segments, especially engineers, now expect some WFA option.
“It’s funny, now it’s becoming a benefit that’s being really used by some really, really interesting companies to retain their top talent.” – John Lee
2) The big blocker: compliance risk
John breaks risk into a few buckets:
- Payroll tax triggers that can start after a single day in some countries.
- Social security coordination and certificates.
- Permanent Establishment (PE) risk if senior, revenue-generating talent stays too long.
- Right to work, immigration, employment law, data and security considerations.
3) The “speedboat,” not the “oil tanker”
- Many legacy mobility suites are heavy, slow, and expensive.
- WFA’s product focus is a fast, decisioning layer: 30 – 60 second risk checks and a simple traffic-light output so managers can act.
- Green = auto-approve, Red = reject, Orange = mitigate with specific steps. That keeps legal spend and operational drag down.
4) What AI actually does here
- Segment benefits by role, cohort, and location to see who values WFA most.
- Score and route requests instantly across payroll, immigration, and PE thresholds.
- Benchmark against peers and surface policy exceptions worth approving.
5) ROI is real, but rarely measured
- Only ~4% of organisations track WFA ROI today.
“Only 4% measure the ROI which is stunning. And this is results that have been consistent from a Mercer survey for the last two years.” – John Lee
- Case examples cited in the show:
- Mercado Libre used AI to tailor benefits and a time-boxed WFA programme, dropping voluntary attrition from c. 14% to 4% in a few years within a key talent segment.
- Spotify reported a 15% reduction in attrition one year after launching its WFA approach.
- Translation: even small retention gains typically dwarf software and admin costs.
Build A Practical WFA Policy (John’s playbook)
- Gauge appetite and risk
Survey employees, quantify lost offers and regretted leavers due to lack of flexibility. Align Legal, Payroll, Tax, Mobility, HR on risk tolerance. - Set hard boundaries
- Countries: Green (entity present), Red (sanctions, security, duty of care), Orange (case-by-case).
- Days: Choose an “up to” cap (e.g., 30, 60, 90) with clear approvals and exception handling.
“Employees do understand work from anywhere doesn’t really mean work from absolutely anywhere. They understand there’s going to be countries… immediately red. Green countries might be where you have an existing legal entity. And then orange countries are the rest where you need to look at them on a case-by-case basis.” – John Lee
- Decision in seconds
Put a traffic-light engine in front of every request. Green = instant approval. Orange = mitigate (e.g., shorten stay, change activities, add certificate). Red = not permitted. - Handle exceptions deliberately
Define who can approve day-limit or country exceptions and what extra mitigations are needed. - Measure before and after
Track retention, offer acceptance, time-to-hire, engagement, request volumes, and legal spend avoided.
Try WFA’s Policy Builder to sketch your first draft
See the WFA ROI Guide with metrics and a maturity check
What To Measure (and show your CFO)
- Talent attraction: applications per role, offer-acceptance rate, reasons for declined offers.
- Engagement & satisfaction: pre/post-trip pulse for WFA users vs. controls.
- Retention: voluntary attrition in eligible segments vs. baseline.
- Efficiency: cycle time to decision; external advisory spend avoided.
- Risk posture: % green/orange/red, issues caught pre-trip, PE and payroll triggers prevented.
“Do we say no, we’re not going to do this, but then we’re losing some of our best talent… or do we say let’s go for it, but then make sure you don’t put yourself into too much compliance risk?” – John Lee
Audience Q&A, distilled
- Can occasional work on holiday cause risk? Sometimes, yes. Some jurisdictions trigger payroll or service PE risk very quickly. Keeping trips short and pre-cleared lowers exposure.
- EOR vs WFA? EOR is for permanent employment in a country. WFA tools cover temporary international trips and decisioning.
- SMB vs Enterprise? The need exists in all sizes. Larger firms feel the ROI fastest because attrition and exceptions are costly at scale.
- Fairness for those who won’t travel? Use AI to personalise benefits. WFA for some, local perks or stipends for others.
“There’s a lot of different segments where having a work from anywhere policy is hugely valuable and can be a real differentiator when you’re comparing to your competitors.” – John Lee
Three Takeaways For HR Leaders
- Start with data. If you do not measure, you cannot defend or scale the benefit.
- Keep it simple to run. A fast, AI-assisted decision layer plus clear rules beats a complex, all-singing platform you never fully adopt.
- Tell the retention story. Model the cost of regretted leavers against a modest WFA investment. The numbers usually speak for themselves.
Useful Links From The Episode
- Connect with John Lee on LinkedIn to request the ROI takeaways and examples.
- WFA Policy Builder:
- WFA ROI Guide:
- Watch the full video here
Donal Brady is Co-Founder and Head of Product at Work From Anywhere, a platform to help companies execute a successful workation policy. He has deep expertise and experience in the world of remote work having spent nearly twenty years working in finance leadership roles with global multinationals like PwC, before entering the world of global mobility with International SOS and then pivoting into the software industry with Accel-KKR backed Smart Communications. He walks the walk with Work From Anywhere, speaking 5 languages, having travelled to 65+ countries and worked in 10.
