Expat Health Insurance Partners
Aetna International
Aetna offers award-winning international health insurance plans to more than 55 million members worldwide. Their plans are tailored to meet the individual needs of you and your family while you are away from your home country, living and working abroad. Get peace of mind knowing you and your family will be protected and have access to quality health care wherever you are, where you need it.
* For a limited time, there is a discount of up to 20% on new multi-member policies and up to 10% on single member policies. This offer is valid until 19 June 2020. See website for details.
Cigna Global
With 86 million customer relationships in over 200 countries, Cigna Global has unrivalled experience in dealing with varied and unique medical situations and delivering high standards of service wherever you live in the world.
You are right in that you would need to first secure a job with an employer in Canada, and thereafter apply for the relevant work permit and visa. You can find more info on our Work Permits for Canada page. However, as you say, it's a pretty complicated process - for example, the employer would have to prove that a Canadian citizen would be unable to do the job you'd be doing.
There are a number of different types of visas, though, and you may find that you are eligible. We have a list of the most common on our Visas for Canada page.
Best of luck!
M