A checklist before you sign your first client across the Canada-USA border

Scott Cundill · 2026-10-29 · Winnipeg

Before you sign, check five things: the currency, the contract, the tax, the paperwork for working across the line, and who you can call when something goes sideways. The Canada-USA border is the friendliest in the world, but it is still a border, and the surprises usually show up on the first invoice, not the first call.

1. Agree the currency, in writing

Canadian dollars and US dollars drift apart week by week. Decide which currency you invoice in, who carries the exchange risk, and how payment will arrive. A small gap on a large contract adds up quickly.

2. Pick the law and the courts

Which province or state's law applies if you ever disagree? It sounds gloomy at the start of a happy relationship, which is exactly when it is easiest to agree. Ask a lawyer who knows both sides to look over the contract.

3. Ask about tax early

Sales taxes, withholding and where your business is considered to be operating can all change once you have clients across the line. A short conversation with an accountant before you sign is far cheaper than one after.

4. Check whether you need to cross in person

Delivering work remotely is one thing. Turning up on site is another, and the rules for working visits differ depending on what you will actually do there. Check before you book the flight, not at the border desk.

5. Line up your people on the other side

Every good cross-border relationship needs a few trusted names nearby: an accountant, a lawyer, a banker, maybe a supplier. The fastest way to find them is through someone who already uses them.

Who can refer me to those people?

The Bridge can. Tell the host what you need, a client, a partner, an adviser on the other side, and if they genuinely know someone suitable they introduce you both, in a short note explaining why. No lists, no cold pitches, and no introductions made just for the sake of it.

The Canada-USA Business Bridge Collaboration Group

Marc Palud holds the Canadian end from Winnipeg. He founded SpeedNetworkingLive.com and hosts The Transformative Human Podcast, and he has spent years building rooms where people truly meet rather than swap cards. The American host seat is open.

This checklist is general, not legal or tax advice, so take the details to your own advisers. Then name the first client you would love to have across the border, and ask who already knows them.

One last item for the checklist: ask your circle for a referral. A client who arrives through someone they trust is the easiest cross border client you will ever win.