I'm from Canada. I'm not an O/O but have 20 years experience in trucking and logistics and write software for O/O's and truckers.
It will depend on where you are going in Canada. We're a pretty big country so you'd have to be a little more specific about a city or region. For example, I'm in Ontario and it's huge on it's own. I'm about an hour from Toronto. So wherever you plan to locate, you should think about being close to where the freight is for your sake as a business person, and your driver's sake for their efficiency also.
The auto industry is usually good and if you plan to locate in Ontario, do yourself a favour and be somewhere close to Kitchener or London. You're close to the American border, on a major highway (the 401) and the heart of the Canadian industry is practically there, with all the auto parts manufacturers and car makers. There's a lot of other industry there too.
That said, if you have up to about 5 trucks, you could put them on with Challenger or Trans-Frt McNamara. Laidlaw is another good one. I'd check out Over The Road (you should be able to find that via Google) - it's a magazine that has listings of different companies that are looking for o/o's and drivers.
Hope that helps, sir.
Shawn
Contrast Logistics Software
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