For companies that you see on those boards, follow their social accounts and maybe the accounts of their founders/leadership. They'll often tweet about postings prior to them even going up on a job board.
Q: How do I make my resume attractive?
One of the most critical parts of remote cultures is being an effective communicator. Since you won't be in an office to bounce ideas around, you need to show that you can express your thoughts. Your resume itself will convey some of this, but if you have links to blog posts/essays that's great to see as well.
Aside from that, always good to see examples of work that you're proud of.
Q: Will I need a Visa if employed by a US company?
Not necessarily. If the company has a Canadian office, they'll likely take you on as a full time employee and pay all the regular benefits and payroll taxes for you. If they don't, you'll likely work as a contractor and will have to decide if you want to incorporate or be a sole proprietor. You do not require a Visa to be a Canadian working for a US company as a contractor.
You are correct that contractors have no insurance/benefits, but that's usually OK because you can negotiate higher wages as a contractor and pay for benefits yourself via something like Blue Cross (https://on.bluecross.ca/health-insurance/health-insurance-so...).
If you have a spouse, it's also possible you're covered under their plan so that's a good thing to check.
Regarding holidays/vacation, it's just something to negotiate as part of your arrangement. If you're "consulting" for one company, you're effectively a full-time employee and will likely have some level of vacation time built in to your contract.
To answer some of your questions:
Q: Where should I start?
Job boards like https://remoteok.io/ and https://weworkremotely.com/ are great places to look for remote work (Parse.ly has posted jobs and hired candidates from We Work Remotely before).
For companies that you see on those boards, follow their social accounts and maybe the accounts of their founders/leadership. They'll often tweet about postings prior to them even going up on a job board.
Q: How do I make my resume attractive?
One of the most critical parts of remote cultures is being an effective communicator. Since you won't be in an office to bounce ideas around, you need to show that you can express your thoughts. Your resume itself will convey some of this, but if you have links to blog posts/essays that's great to see as well.
Aside from that, always good to see examples of work that you're proud of.
Q: Will I need a Visa if employed by a US company?
Not necessarily. If the company has a Canadian office, they'll likely take you on as a full time employee and pay all the regular benefits and payroll taxes for you. If they don't, you'll likely work as a contractor and will have to decide if you want to incorporate or be a sole proprietor. You do not require a Visa to be a Canadian working for a US company as a contractor.
You are correct that contractors have no insurance/benefits, but that's usually OK because you can negotiate higher wages as a contractor and pay for benefits yourself via something like Blue Cross (https://on.bluecross.ca/health-insurance/health-insurance-so...).
If you have a spouse, it's also possible you're covered under their plan so that's a good thing to check.
Regarding holidays/vacation, it's just something to negotiate as part of your arrangement. If you're "consulting" for one company, you're effectively a full-time employee and will likely have some level of vacation time built in to your contract.
Parse.ly has amazing holiday and parental leave policies and we're hiring https://www.parse.ly/jobs/#frontend-engineer :).
You can also learn more about the how and why of our distributed team here https://blog.parse.ly/post/3203/the-how-and-why-of-parse-lys....