You’re sitting in a coffee shop in Toronto or maybe a home office in Vancouver, and a recruiter from Austin pings you. The salary is in USD. It’s huge. Suddenly, the idea of working in the US from Canada isn't just a "maybe someday" thought—it’s a "how do I do this by Monday" reality.
But here’s the thing. Most people think it’s just about getting a TN visa or a laptop. It's way messier. You’ve got tax treaties that feel like they were written in ancient Greek, social security quirks, and the very real possibility of the IRS knocking on your door while the CRA is already sitting in your living room.
I’ve seen people jump into these roles without realizing that "remote" doesn't mean "borderless." If you stay in Canada while working for a US company, you're basically a tax unicorn. If you move across the border, you’re an expat. Both paths are great, but the paperwork will kill your vibe if you aren't ready for it.
The TN Visa: Not the Magic Wand You Think
Let’s talk about the TN (Treaty National) status. It’s the darling of the US-Canada professional world. Created under NAFTA and preserved under the USMCA, it allows Canadian citizens in specific "professional" categories to work in the States.
It’s fast. You can literally get it at the border.
But it’s also incredibly rigid. If you’re a "Management Consultant," the border agent is going to grill you. They want to see that you aren't just an extra pair of hands but someone providing high-level strategy. If you show up with a job offer for "General Manager" under a Management Consultant category, you’re probably going home. Honestly, the CBP (Customs and Border Protection) officers have a lot of discretion. One guy at the Peace Bridge might be having a great day; the lady at Pearson might decide your degree doesn't quite match the job description.
You need a wet-ink signature on your offer letter. Digital isn't always enough. You need your original degree. Not a photocopy. It’s these tiny, physical details that trip up the smartest engineers and nurses.
Staying North: The Remote Work Reality
What if you don't want to move to Texas? What if you want to keep your Canadian healthcare and just collect those sweet American dollars?
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This is where working in the US from Canada gets complicated for the employer. If a US company hires you as a standard W-2 employee while you live in Ontario, they might accidentally create a "permanent establishment" in Canada. That’s a nightmare for their HR department. It means they might have to register as a Canadian business, pay Canadian corporate taxes, and follow provincial labor laws.
Most US startups won't do that.
Instead, they’ll ask you to be a contractor. You send an invoice; they send a wire transfer. Easy, right? Well, sort of. Now you’re a business owner in the eyes of the CRA. You have to handle your own CPP contributions, your own health insurance, and—this is the big one—GST/HST if you start billing other Canadian clients too.
The Tax Trap: Form 1040-NR and the Treaty
You cannot escape the IRS. Even if you never set foot in America, if you’re working for a US firm, there’s a paper trail.
If you are a resident of Canada, the Canada-US Tax Treaty is your best friend. It’s designed to prevent double taxation. Basically, you pay your taxes to Canada first because that’s where you live and breathe, and then you claim a Foreign Tax Credit on your US filings. Or vice versa, depending on the "tie-breaker" rules.
But you still have to file.
Specifically, you’re looking at Form 1040-NR (Non-Resident). If you’re physically moving to the US, you’ll deal with the "Substantial Presence Test." Spend more than 183 days there over a three-year weighted period, and the IRS claims you as one of their own. Suddenly, your worldwide income—including that rental property in Montreal or your TFSA—is subject to US reporting.
Wait. Let's pause on the TFSA.
The US does not recognize the Tax-Free Savings Account as a "tax-free" vehicle. To the IRS, it’s a foreign trust. The paperwork (Forms 3520 and 3520-A) is expensive to file, and the penalties for getting it wrong are astronomical. Most cross-border tax experts will tell you to liquidate your TFSA before moving to the US. It’s heartbreaking, but the tax bill otherwise is worse.
Healthcare: The Great Divide
In Canada, we complain about wait times, but the bill is zero. In the US, the care is world-class, but the bill can be the size of a mortgage.
If you’re working for a US company while living in Canada, you’re fine. You keep your provincial coverage (OHIP, MSP, etc.). But if you move, you need to negotiate your benefits package like your life depends on it. Because it does. You want a PPO, not just an HMO, if you want choice. You need to look at the "out-of-pocket maximum."
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Also, your Canadian credit score? It’s basically useless once you cross the border. You’re a ghost.
I’ve seen executives making $200k a year get rejected for a basic credit card at a US bank because they have no "US history." Pro tip: If you have an American Express card in Canada, use their "Global Transfer" program. They’ll use your Canadian history to open a US card for you. It’s a lifesaver for getting your first apartment or a car lease in California.
The Social Security Totalization Agreement
There is a silver lining. Canada and the US have a "Totalization Agreement." This ensures you don't pay social security taxes to both countries for the same income. It also allows your years of work in Canada to count toward your US Social Security eligibility and vice versa.
If you’re sent by a Canadian company to work in the US for less than five years, you can often stay on the Canadian Pension Plan (CPP). You’ll need a "Certificate of Coverage." It’s a boring piece of paper that saves you thousands.
Realities of the Daily Grind
Working across time zones is one thing. Working across cultures is another.
Americans move fast. The "at-will" employment culture is a shock to Canadians used to lengthy notice periods and severance protections. In many US states, they can fire you because it’s Tuesday and they didn't like your tie. No notice. No explanation.
As a Canadian working in the US from Canada, you need to be aware that your provincial labor protections (like the Ontario Employment Standards Act) might not apply if your contract says it's governed by the laws of Delaware. Always have a lawyer look at the "Choice of Law" clause.
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The 401(k) vs. RRSP Puzzle
If you move to the US, you’ll likely get a 401(k). Can you transfer your RRSP into it? No.
Can you leave your RRSP in Canada? Yes, but you need to tell your Canadian brokerage that you’re a non-resident. Some brokerages will actually close your account because they aren't licensed to manage money for US residents. It’s a massive headache.
Conversely, when you move back to Canada (and many do), your 401(k) can be brought back, but the "rollover" process is delicate. If you just withdraw the cash, the IRS takes 30% off the top, and the CRA takes their cut too. You need to use a specific treaty-based transfer to move those funds into an RRSP without getting destroyed by taxes.
Moving Your Stuff
Don't forget the physical border.
If you’re moving your household goods, you need a Form 3299. You’ll need to prove that your items are for personal use and have been in your possession for at least a year. If you have a car, check the "compliance label" in the door frame. If it doesn't say it meets US EPA and DOT standards, you might have to pay for expensive modifications or, in some cases, you can't bring it at all.
Actionable Steps for the Cross-Border Leap
It's a lot. But it's doable. If you’re serious about making this move or taking that remote US role, don't just wing it.
- Get a Cross-Border Accountant: Not a Canadian accountant. Not a US accountant. You need a specialist who understands the 5th Protocol of the Tax Treaty. This is non-negotiable.
- Audit Your Assets: Look at your TFSA, your RESP, and your non-registered investment accounts. Identify which ones will become a "tax drag" if you become a US resident.
- Negotiate the "Employer of Record" (EOR): If you're staying in Canada, ask the US company to use an EOR like Deel or Remote.com. They handle the Canadian payroll, taxes, and compliance so you don't have to act like a one-person corporation.
- Check Your Passport and Degree: For a TN visa, your job title must closely match the USMCA list. If you have a degree in Biology but you're applying for a Software Engineer role, you’re going to have a hard time at the border.
- Set Up a US Dollar Account: Use a bank that has a presence in both countries (like TD, RBC, or BMO). It makes transferring money between your "lives" significantly cheaper than using standard wire transfers with 3% hidden fees.
Working for a US company is one of the fastest ways for a Canadian to boost their career and their bank account. The "brain drain" is real for a reason—the pay gap is often 30% to 50% once you factor in the exchange rate. Just make sure you aren't spending that extra 50% on tax penalties and legal fees because you forgot a form.
The border is invisible for a Zoom call, but it's very real for the tax man. Respect the line, and you’ll be fine.