I’m a Canadian software developer exploring the possibility of working remotely for a US-based company. For those who have done this, did you set up a US company or work as a contractor instead of an employee? What were the tax and legal implications of your arrangement in both Canada and the US?

Additionally, did your US employer recognize Canadian statutory holidays, and overall, was the effort involved in navigating these complexities worthwhile? I’d appreciate any advice or insights based on your experiences.

I did this for a few years.

I just worked as an independent contractor / self-employed - didn't seem worth it for me to set up a company as I didn't have expenses to declare for tax purposes. As an independent contractor you just file Canadian taxes, its pretty easy.

I think vacation policy is all over the map - most probably won't recognize Canadian holidays but if its a smaller startup they may be more flexible. Also worth keeping in mind US companies offer fewer vacation days in general on avg. than Canadian companies.

Overall I would recommend it! Pay is better, complexities are not so bad.

The only time I really worked with Canadians is when a US-based company did a small aqui-hire of a Canadian firm.