If your current US employer is willing to continue your employment as a remote worker in Canada, then migrating to Canada after your H1-B expires can be relatively easy.
It is not your H-1B experience in the US that can help you, but the fact that your current US employer can offer you a job in Canada. Learn more about relocation, visas and permanent residency in Canada with this Government of Canada fact sheet.
US employers work with Canadian-based Professional Employer Organizations (PEOs) to employ remote workers in Canada. We act as your new employer of record in Canada and assign you to work for your former US employer as their employee.
As a Canadian permanent resident, you will need a US-issued B1/B2 multiple entry visitor visas in order for you to cross back into the US to meet your US employer. This B1/B2 visa is straightforward to get, but it doesn’t permit you to work on US soil. However, it can be used for business meetings with your current US employer (now officially your client), and also to attend trade conferences and training seminars in the US.