12 Questions: Anastasia Pshegodskaya on the Future of Cross-Border Hiring
The compliance, collaboration, and strategy insights talent leaders need to hire globally in 2026.
Anastasia Pshegodskaya, Global Director of Talent Acquisition at Remote, has built global recruiting systems from the ground up at companies like GitLab, Uber, and Dell. She’s deeply passionate about how technology shapes people and work, and now leads cross-border hiring at Remote.
We asked Anastasia to weigh in on the 12 most pressing challenges in global talent today. Below, she shares her 2026 playbook for cross-border hiring, offering tactical advice on building scalable processes, enabling managers, and maintaining alignment across a distributed workforce.
By: Anastasia Pshegodskaya, Global Director, TA at Remote
Start with the "Why," not the "Where"
Remote-first work is normal now, but cross-border hiring still breaks in predictable places. What is the hardest part of making global hiring work well in 2026?
Indeed, we are seeing remote work becoming a new norm and standard in the industry. However, as employers normalize the remote-first approach, they often overlook the complexity and the “boring” side of hiring and employing people globally.
Staying compliant while hiring abroad remains one of the biggest challenges for companies today, as HR teams need to stay on top of ever-changing regulations across multiple jurisdictions. Compliance issues can range from misclassification of employees, taxation, leave entitlements, and payroll processing. Errors create real legal, financial, and reputational exposure. Companies that get this right unlock access to a broader, more competitive talent pool.
Another big challenge is a lack of direction and strategy behind the new talent markets you want to unlock. Entering an unknown market always comes with its own challenges, so you should have a clear HR and TA strategy that defines what business problem you are trying to solve.
I always say that it’s okay to start small; you don’t need to boil the ocean and suddenly start hiring in 200+ countries across the globe.Make sure you do your homework and ask yourself:
-Can hiring in a certain location bridge the talent pool gaps you see?
-What is the cost associated with hiring and managing employees there?
-What is the business problem you will solve? How are you going to measure success?
When a leader says “let’s hire this role anywhere,” what are the first questions you ask to pressure-test whether that is realistic?
There are a lot of questions you would want to ask, but I would always start with a simple Why? question.
What is the business need or challenge that we are trying to solve by hiring in a specific area and then pressure test whether hiring is the optimal solution.
If it is, you would want to confirm whether you can hire compliantly in the location:
-Do you already have a business entity there?-If not, are you planning to hire via an Employer of Record or a Contractor of Record?
-How are you classifying this hire - as an employee or a contractor?
Each of these models carries different legal obligations and implications, and that assessment should happen before moving forward.
Once that’s clear, ensure the person is set up for success operationally. What timezone overlap will they have with the team? How will that influence decision-making speed and collaboration? Is onboarding structured and well-supported?
Each of these steps ensures the business is scaling responsibly while reducing risk.Global access doesn’t mean local costs.
In 2026, which roles or skill sets are you seeing become competitive everywhere, even when companies can hire globally?
We’re seeing heightened competition for roles in AI and machine learning, cybersecurity, and specialised engineering, particularly cloud architecture and data engineering.Product designers with strong UX research skills and senior technical leaders who can operate effectively in distributed environments are also in high demand.
Even with global hiring enabled, top talent in these areas commands competitive compensation regardless of location.Access expands, but competition remains global.
When a country or region starts to get crowded, what do you notice first in the hiring market that tells you the advantage is disappearing?
As a market becomes more competitive, the first signs are often visible in compensation pressure and operational friction. Salary expectations rise and stop aligning with budgets, making it harder to close candidates within planned ranges.
You may also see longer time-to-hire, more counteroffers, and shorter offer decision windows. When multiple global employers enter a market at once, the cost and speed advantages narrow very quickly.Asynchronous work is the new operational default.
At a remote-first company, what does “good team design” look like when you are hiring across many countries and time zones?
Working in a globally distributed team requires asynchronous-first collaboration. Teammates often don’t work the exact same hours and must be able to pick up tasks or catch up independently. Clear written and video documentation, decision logs, and proactive handoffs ensure work progresses regardless of how many team members are online.
When I think about my team structure, my goal is always to align it with our hiring needs and company priorities — starting from key hiring focus areas and the subject expertise we need on the TA side, all the way down to geographical aligment.For roles demanding swift decisions, what are the most effective rules you've observed for managing time zone differences and facilitating collaboration?
In cases where speed is essential, teams should define an explicit overlap window for real-time decision making. This window can be reserved for time-sensitive collaboration, while other work continues asynchronously.
If overlap isn’t viable, structured handoffs and well-documented workflows maintain momentum. Shared data sources and connected workflows reduce bottlenecks and speed up decisions across time zones.Remote-first companies still do some in-person moments. In 2026, when does being in the same place actually change outcomes enough to justify travel or relocation?
There are instances where in-person gatherings make a measurable difference, such as annual planning sessions, leadership off-sites, or complex strategic discussions. The impact justifies the travel.
In-person collaboration can also help accelerate trust in high-ambiguity situations, such as negotiation or conflict resolution.
If distributed teams repeatedly feel blocked by time zone or coordination challenges, that often signals a need to revisit operating design rather than default to relocation.
However, after 8 years of working for all-remote companies, I must say thatyou should never underestimate the complexity and costs of organizing in-person meetings, and I’d never default to those unless ROI is clear.Avoiding Cross-Border Pitfalls
What are the most common reasons cross-border hires fail after they start, even when the candidate looked great in process?
Common issues include onboarding and support gaps, where processes and working styles don’t translate cleanly across locations.
This can mean the employee doesn’t receive sufficient structure or context in the first weeks or months, leading to confusion and disconnect.
Timezone friction can make it harder for new hires to integrate with the broader team, access decision-makers, and resolve obstacles quickly. Misaligned expectations around compensation, levelling, and pay transparency across markets can also lead to dissatisfaction and early attrition.
The fundamentals are consistent across markets: clear expectations, strong onboarding, and consistent communication — both sync and async.For companies hiring internationally, what people-related risks are you watching more closely in 2026 (for example compliance, misclassification, pay expectations, or candidate fraud)?
Compliance risk remains the dominant concern.In our recent Global Workforce Report, most HR leaders reported compliance challenges when operating in other countries. Misclassification risk, particularly distinguishing between contractors and employees, is a key pain point.
Data protection and payroll security are also critical areas of focus.At the same time, pay expectations and pay transparency requirements are increasing. With the EU Pay Transparency Directive coming into effect in June 2026, companies need clear and defensible compensation frameworks across markets.
What should make a TA leader stop and say “we should not hire this cross-border,” even if the talent is available?
Compliance must be the priority when hiring globally. If the team cannot hire compliantly without taking shortcuts or workarounds, such as engaging someone as a contractor while treating them as an employee, that’s a signal to pause. The compliance risk is too high.
Cross-border hiring should not proceed if it exposes the business to significant legal, financial, or reputational risk.Building a Sustainable Hiring Infrastructure
If you were redesigning a global hiring strategy today, what is one decision you would make earlier than most teams do, because it is hard to fix later?
Before publishing a job ad, decide on your global employment operating model - whether hiring through your own entity, via an EOR, or as a contractor where appropriate.Lock in clear guardrails early.
Missteps at this stage can cost you the candidate and create compliance exposure that is difficult to unwind later.
Standardising and simplifying your global employment infrastructure early also prevents an unscalable patchwork of tools that complicates payroll, onboarding, and leave management as you expand.What do you think TA leaders need to build in 2026 so cross-border hiring stays sustainable in 2027 and beyond (process, data, onboarding, manager enablement, something else)?
To sustain cross-border hiring into 2027 and beyond, TA and HR teams should invest in three core areas:
First, build an integrated global employment infrastructure that reduces reliance on disconnected tools and manual processes. Fragmented systems create data silos and slow down onboarding, payroll, and compliance.
Second, develop strong compliance playbooks with clear, country-specific guidance for each hiring model. Teams should understand the legal distinctions between entity hiring, EOR, and contractor arrangements before extending offers.
Third, prioritise manager enablement. Leaders need clear frameworks for async collaboration, remote onboarding, and performance management across time zones. Many cross-border hires succeed or fail based on manager capability.
Together, these investments create the foundation for scalable and compliant global hiring.
Connect with Anastasia Pshegodskaya on LinkedIn.
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