Managing International Payroll for Contractors

By Ryan Doyle, CFO at Worksuite

In one of my early roles as a startup finance leader, I needed to execute a payment in Malaysian Ringetts to a contractor my CEO wanted to hire. The problem was, my bank didn’t support it. I had no idea how to solve this problem. It took too many hours of my time. And worse, it delayed the start of our project.

Once was bad. But then this problem amplified to six other countries. I started spending all of my time on the wrong activities. Instead of building the business I was trying to collect documentation and pay contractors. The problem wasn’t in the payment, but our finance workflows.

At first, it seems simple. Hire a contractor. Send a payment. Move on. But once you start scaling — across regions, currencies, tax regimes, and teams — things get messy fast. Payments get delayed. Tax compliance breaks down. Finance and legal scramble to plug holes, and your best freelancers start looking elsewhere.

In this post, I’ll unpack what makes international contractor payroll so deceptively complex, how I think about designing systems that scale, and the operational moves we’ve seen finance leaders make to stay compliant and competitive.

The “Easy” Part of Paying Global Contractors

Let’s be honest: the actual act of moving money is easy. Wire it, PayPal it, Wise it. There’s no shortage of fintech vendors ready to help you click “send.”

But that’s not your bottleneck. Your bottleneck is everything around the payment:

• Collecting the right tax forms
• Routing invoices for approval
• Matching payments to contracts and scopes
• Staying compliant across 15+ tax jurisdictions
• Reconciling FX volatility in your budget vs. actuals

If you're still stitching this together with Google Sheets and shared inboxes, you’re not alone. But you're also not going to scale it. And you certainly are not providing an optimal experience for your freelance talent.

Where Global Payroll for Contractors Breaks Down

Here’s where most companies run into trouble — especially if they’re scaling fast or managing contractors in multiple countries.

1. You Don’t Have the Right Tax Documents

Before you pay a contractor, you need to confirm you’re withholding and reporting correctly. In the U.S., that means collecting a W-9 for domestic freelancers and a W-8BEN for non-U.S. contractors.

Miss this step, and you're exposing your company to:

• 24% backup withholding penalties
• IRS compliance risk
• Painful audits during due diligence

2. Your Teams Don’t Know Who’s Been Paid (Or Why)

If Procurement is negotiating scopes, Legal owns contracts, and Finance is pushing payments… who owns the audit trail?

Without a unified freelancer management system (FMS), I’ve seen companies lose visibility over:

• Who’s approved to pay
• Whether the contract is current
• Whether the deliverables were met
• Whether payment terms (Net 15? Net 30?) are being honored

This lack of control costs real money — in rework, in delays, in contractor churn.

3. You’re Not Planning for Currency, Timing, or Volume

If you’re running a lean finance team and onboarding contractors globally, you need to plan around:

• Local currencies (and FX impact)
• Payment timing (bank holidays, approval delays)
• Volume (can your AP team handle 50 invoices a week?)

A system like Global Pay lets you batch payments, automate FX calculations, and track everything from invoice to disbursement — in 190+ countries. And most importantly, it integrates upstream (contracts, scopes) and downstream (ledger, reporting).

What “Good” Looks Like in International Contractor Payroll

Here’s what I recommend to finance teams building global freelance programs:

Build a Single Source of Truth

Centralize contractor data — tax status, location, contracts, payment preferences — in one system. No more scattered files or manual reminders.

  Automate Tax Compliance

Set rules based on geography. If a contractor is U.S.-based, prompt a W-9. If they’re international, trigger a W-8BEN upload. Worksuite handles this at scale.

Set Clear Payment Workflows

Streamline your payment process for consistency and accountability. Define:

• Who approves invoices
• What documentation is required
• How payments are batched or scheduled
• What happens if a bank transfer fails

Then automate it. The fewer emails you send about “where’s the invoice,” the better.

   Plan for Audit and Reporting

At some point, someone — a CFO, a tax authority, or a potential investor — will ask: “Who have we paid, for what, and was it compliant?”

You don’t want to start that search in your inbox. With a freelancer management software platform, you already have the answer.

Final Thoughts: Run Global Payroll Like a System, Not a Series of Exceptions

This isn’t just about contractor payments. It’s about building a finance function that scales with speed and integrity.

When your team has to make judgment calls on every invoice, you create bottlenecks and risk. When you build structured workflows, you create leverage — and that shows up everywhere: in cash flow, in compliance, and in contractor satisfaction.

Ready to take the chaos out of global contractor payments?
Worksuite's Global Pay gives finance teams the tools to automate compliance, streamline workflows, and scale with confidence.

Pay freelancers across 190+ countries and 120+ currencies — book a demo today.

About the Author Ryan Doyle is the CFO at Worksuite, where he leads global finance strategy and operations. With a background in SaaS finance and GTM enablement, Ryan helps finance leaders design systems that scale, surface risk, and support smarter decisions. He writes for operator-first teams who want fewer dashboards and more clarity on what’s driving real growth.