Global hiring: How to overcome the 5 biggest challenges of distributed work

Five ways to overcome the most common challenges.

As talent shortages threaten to cost trillions of dollars in lost revenue, organizations are expanding their searches beyond the boundaries of their headquarter cities and countries to around the globe. Global remote hiring has become more common, HR and People teams are at the forefront of reimagining the workplace and employee experience in this new world of work.

As Head of Employee Experience at Oyster, a global employment platform that enables companies to hire compliantly in 180+ countries, I’ve helped scale our team from 75 people in 30 countries to 600 people in 70 countries (and counting) in just the past year.

Growing this rapidly on a global scale has its challenges. How do you create an employee experience that is fair, equitable, and consistent across 70 countries?

Based on what I’ve learned so far, here are five ways to overcome the most common challenges when hiring your first globally remote employees.

Ensure time zone compatibility 

If your company has decided to hire talent across borders, you might be tempted to start hiring from as many different countries as possible right away. After all, the more geo-diversity, the better, right?

Yes and no. Think about the employee experience and what it’ll be like to be the only person awake, or the only person working, in a particular country, region, or time zone. Imagine how isolating it might be to start a new remote job and be separated from the rest of the team by several time zones.

In other words, be thoughtful about how you approach global hiring when you’re scaling a team. Will the new person have some hours of overlap with their manager and/or teammates? If not, what processes and cultural norms do you have to address this or support them? Try starting with a time zone based approach, and expanding your team gradually as you increase opportunities to overlap working hours. A good way to do this is to focus on documentation and asynchronous work through apps like Loom and Notion, and to “follow the sun” as teams hand off work to colleagues around the globe.

Be mindful of cultural differences 

In the complex and fast-moving world of global employment, it can be easy to get caught up in the details of legal compliance and workplace design—all while forgetting about the cultural considerations of having teammates from various countries.

That might mean being aware of varying holidays and religious observances, as well as taking into account cross-cultural issues that can be nuanced and complex. At Oyster, I’ve experienced firsthand just how complicated it can be to create ‘one global culture’ across dozens of countries that each have their own traditions, political environments, and social norms. Here are a few tips on how to be mindful within your organization: 

  • Flexible work hours and generous PTO to allow folks to celebrate or observe their local and chosen holidays, rather than adhering to one global schedule. This pairs well with a #celebrate-around-the-world channel on Slack for people to share what they’re celebrating and invite others to learn about their holidays.
  • Opt-in social chats and photo sharing through watercooler apps like Donut so team members can meet folks they might not usually interact with from all around the world.
  • A #tandem-language-learning channel to connect people based on the languages they speak and would like to learn, creating a culture of knowledge sharing.

True inclusivity means taking all of this into consideration. Don’t overlook the challenges of creating a unified employee experience across a globally and culturally diverse team. Be thoughtful and intentional as you proceed.

Lean on technology for HR necessities like payroll, compliance, and benefits

Most People leaders are under-resourced. We’re given an incredible scope of work that often includes recruiting, compliance, payroll, employee experience, employee relations, performance management, documentation, and more. It’s unrealistic to expect a small People team to take on the additional burden of doing everything that’s required to hire compliantly across borders.

And yet, I understand why some folks might be hesitant to use a global employment platform. When I was starting out over a decade ago, I was very wary of Employer of Record (EOR) and Professional Employer Organization (PEO) services. I cared deeply about the employee experience and didn’t want to ‘outsource’ any of it to some other company. I didn’t trust them to care for my colleagues with the same level of detail and thoughtfulness that I would, and didn’t want to take chances on things as important as ensuring people received their paychecks and had access to healthcare.  

However, global employment platforms have come a long way, and can in fact take care of your teammates in a way that meets your high standards. Ideally, they should be a partner—an extension of your own team and company culture. Don’t waste your time figuring out how to process payroll, create compliant time-off policies, or offer benefits in every country around the world.

By leaning on technology to handle all that, you can focus on the human experience and connection that matters most in a globally distributed environment. With all of the employment necessities taken care of, there’s plenty of space for People leaders to make their own unique culture shine. 

Always consider equitability in the employee experience — no matter the location 

People teams used to focus on the legal and logistical challenges of global remote hiring, like the aforementioned payroll, compliance and benefits. But with that burden removed by technology, there’s now a greater focus on equitability.

In other words, it’s no longer just ‘How do I hire this person in this other location?’ Now the questions are: ‘How do I design an employee experience that is fair and equitable for everyone, regardless of what country they’re in? How do I build programs, policies, benefits, and hiring practices that can scale for a global population?’

Companies need to think about equitability right from the start. How do you plan to offer equitable benefits, compensation, perks, and manage general work norms? A global employment platform can help with some of this, but a lot of it is on you as a company to think through what you want the ‘workplace’ to look and feel like for your global and remote employees.  

A great example is Quora, where they’ve put a lot of thought into equalizing the employee experience across Ireland, India, Canada, U.K., U.S., Poland, Bangladesh, Mexico, Brazil, and beyond. They start every conversation regarding any new perk, benefit, or material changes by first asking, “Can we do this internationally?” They never say, “We’re going to do this domestically and think about international down the road.” In some cases, providing the exact same benefits or perks in the U.S. vs. other countries has proven difficult, so when they can’t find the same solution, they look for alternatives to offset the difference as closely as possible.

Prioritize trust 

In a traditional co-located workplace, trust often develops naturally from seeing the same people every day, bumping into each other in the breakroom, or realizing that you share a bus route to the office. But in a distributed workplace where you only know your teammates online, you have to work harder to get to know people and build relationships. 

In a globally distributed environment, it’s incredibly important for trust to be a part of building strong working relationships. You have to engage with your colleagues, whether that’s in virtual social spaces at work or just by being a reliable teammate, to collectively earn and build that trust. It takes a bit more effort and intentionality, but it’s critical to building a strong foundation for asynchronous work—especially if you and your teammates rarely overlap in working hours.

A company needs to function as a community where relationships are built on foundations of trust and mutual accountability. Recognize that everyone has different thresholds and narratives for what it looks like to trust one another, and that for some, it may take more time to open up or to be comfortable being vulnerable with others.

As People leaders, you are critical strategists and conveners when it comes to designing a healthy, thriving, trust-filled work culture. It’s not all on your shoulders to execute, but your thought leadership is massively important in encouraging your executive partners to act in accordance with your company values as you embrace a new way of working together.


The rise of remote work and global remote employment means that People leaders have the opportunity to design and shape the future of work—not just how people work, but how people relate to work and how they experience their working lives. 

That’s what motivates me every single day: I feel excited and optimistic about building a world of work that is more human-centric, compassionate, and inclusive. Let’s step into that future together.

Get started today and unlock the future of global hiring.

About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, hire, pay, manage, develop, and take care of a thriving distributed workforce. Oyster lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

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