Bear in mind that the US (IRS) requirements for independent contractors are not really relevant here. The Canadian legislation is what counts. Citizens are classified based on the legislation of the country in which they are working.
(1) Beware of misclassification if hiring someone full time as a contractor in Canada. In this case the fact that the employee is planning to pick up a side gig is a good indicator they are a genuine contractor instead of a disguised employee. Similarly it helps if the worker provides their own equipment and has responsibility for their own working hours.
(2) Do not offer health and other benefits directly or via an allowance as this is the act of an employer.
(3) Instead build them into the total salary e.g. increase salary by 5k.
Lastly if engaging as a contractor make sure it is for a fixed term (e.g. 6-12 months). Towards the end of the contract initial duration both parties can assess whether the setup still works or whether an employed solution might be more appropriate.
If you have a disability, then the right to work remotely is covered as an accommodation under the Americans with Disabilities Act (ADA). Otherwise it really depends on the employer and manager.
Those companies may feel they have access to enough talent in the USA. They may have restrictions with data protection or security. They may be worried about timezones or communication. Or they may be worried about complying with foreign employment and tax regulations.
You can be employed through a third party deployment company (ArbeitnehmerÜberlassungsGesetz) for up to eighteen months. Such companies (known in other countries as Employer of Record / GEO / PEO / Umbrella companies) have an AÜG license.
We offer this to our clients in Germany. After eighteen months your company could setup (in order of complexity) a representative office, branch or subsidiary. Or you could pursue one of the self employed models.
In the USA the Department of OHSA specifically says that it (and the employer) don't bear responsibility for a home based work site. They won't do site inspections and the best they can do is give tips to the worker and have the worker complete a self-assessment. Overseas this is viewed very differently. e.g. in Australia and UK the employer is responsible for worker safety even if they are working from home.
"OSHA will not conduct inspections of employees' home offices.
OSHA will not hold employers liable for employees' home offices, and does not expect employers to inspect the home offices of their employees.
If OSHA receives a complaint about a home office, the complainant will be advised of OSHA's policy. If an employee makes a specific request, OSHA may informally let employers know of complaints about home office conditions, but will not follow-up with the employer or employee."
Sense of pride and loyalty is generally not a problem. For many (most?) people working remotely allows them to better balance work and life. It often makes it easier for them to do things that are important to them.
One of the ways people "pay that back" is with loyalty and engagement. Also if working remotely gives them opportunities which they can't get elsewhere they might have a higher attachment to keeping the job.
Taking responsibility for work and work hours also comes with the territory. If you can't do this, you can't work remotely. The more common issue that remote employers have is prevent overwork and burnout.
Feeling connected to each other is a bit more complex. Remote companies need to be deliberate about this, especially as they scale. It depends a lot on the way they are constructed. A company that is remote but all within one region can have a synchronous culture. This influences how workers interact. If the company is spread across many timezones they are more likely to have an asynchronous culture and need different ways to interact and build bonds between people. It is possible, just requires effort. I talk about how we do this on the Collaboration Superpowers podcast https://www.collaborationsuperpowers.com/232-getting-to-know...
I think the most public remote companies are also companies who are quite thoughtful about why they exist and what they want to be. Which are good places to start when creating vision and objectives!
That suggests a lack of trust or a reliance on synchronous communication. Both of which don't work great in a remote environment, in my experience. It does seem to work for some people who want to replicate a co-located office experience.
I wonder if there are additional restrictions based on being in financial services. It may require different licenses, registrations, insurance and employer regulations (e.g. different collective bargaining agreement) compared to traditional industries.
Same. You can standardise equipment allowances but you can't standardise co-working costs, especially if you have international workers. Wework cost us roughly USD 700 per head in Sydney, USD 500 in London and USD 300 in Madrid.
I don't see much of this within hybrid companies and don't see why it would occur. The whole point in a hybrid setup is you get to choose what suits you. If you want to work in an office with people, choose that. If you prefer to be remote, work remote.
People don't get paid more in San Francisco because they deliver more value than a worker in New York City or London. San Francisco rates are high because of geographic scarcity of talent in that location. Over the long term remote is going to reduce SFBA rates, not propagate them.