My understanding is that Canadian residency isn't particularly strict, but Canadian citizenship is very strict. Besides, most of the companies in question (e.g. Amazon, Google, Microsoft, etc) already have subsidiaries operating in Canada so employment via the Canadian subsidiary is not an issue.

The program that allows anybody to apply for residence is called Express Entry.

They offer something like 4200 positions every 2 weeks, or about 100k per year.

My understanding is that unless you're at the very top of the list (it's score based) you're likely to be waiting a long time.

Edit: For example the last drawing required you have a score of 471 or above. A 28 year old Indian person with a CS degree and 6 years of job experience who has perfect English scores would only have 441 points.

You also have provincial programs which have different/maybe more lax requirements than express entry. Once you get PR, citizenship is just 3 years away.

4 years effectively. It takes almost 12 months to process the citizenship application.

There's no prohibition for remote work per se. The American company just needs to set up its legal presence in Canada since only Canadian companies can sponsor immigrants. That would still be a barrier to small companies so I expect the PEO (Professional Employment Organization) industry to come up with a way to make this possible at any scale. And that's before Canada changes IRCC regs to help this use case, which they could very well do.

Which is why I mentioned that there are Canadian companies that handle hiring the employee and sponsoring the Canadian work visa, invoicing the company in the US, taking the cut and paying the employee the rest.

https://syndesus.com/why-u-s-companies-need-a-peo-to-recruit...