I'm Peter Roberts, immigration attorney who does work for YC and startups. AMA

Good morning,

I am a dual US / Canada citizen and currently living & working in the US.

I am looking into moving to Canada, and was wondering what kind of issues I could run into if I wanted to continue working for the US company while living in Canada.

I am working for a small sized start-up, and I am pretty certain they have no experience in this kind of thing, so I wanted some more info before breaking the ice.

Thank you

This is a payroll/tax issue. Many employers in these situations use an Employer of Record, such as Deel, to employ U.S. citizens living and working abroad but you also could be employed directly as a W-2 employee.

Working as a W2 employee from Canada would likely cause tax and filing headaches with the Canadian Revenue Agency (CRA), although the salary differential between US/Canada might make this worth it (you just have to be careful). You may also have cashflow issues come tax-time as you will have a large tax Canadian tax burden at the end of the year since your employer would have only withheld/remitted to the IRS, so you would need to file a US return to get back all the income tax that was withheld by your employer.

Disclaimer - not a lawyer but also went through this process, in the end my employer decided to switch me to a contractor.