People with Toronto PhDs frequently get jobs in America, especially if they work in a medieval or early modern specialty. McGill, Queen's, Alberta, UBC and Western Ontario PhDs sometimes do, too, but (and I'm basing this on the job placement information these departments post on their sites) usually at smaller regional schools. Aspire, are there any factors that would rule out your teaching in Canada? I'm entirely a product of the Canadian system so I am naturally a booster, but in any case I think there are many good things to be said for it.