There are a couple of issues here:
Utilities will allow any type of customer-owned transformer, but require that the site be primary metered so that the meter can account for the transformer losses. This would be very expensive for a supercharger site since it would require an outdoor-rated high voltage switchgear with metering compartment.
My suspicion is that the Supercharger equipment is designed for 480 volts from the utility. In that case, the utility would supply power at 277/480 volts and meter at that level. Tesla would, in turn, take that level of power and do with it what they may.
Canadian utilities do not provide 277/480 volt transformers, so there is that. Even if Tesla supplied the transformer, it would have to conform with utility standards for losses if it is to be metered on the secondary side. To further complicate matters, metering in Canada is subject to Measurement Canada rules and requirements, and I don't believe there is a meter approved for that voltage here. Sure, there are US meters that would work, but Canadian utilities can't use them since they wouldn't be "sealed" by Measurement Canada.
This issue has come up at some CHAdeMO sites. The utility supplies and meters power at 347/600 volts and the installer has to supply an additional transformer to step the 347/600 volt feed down to 277/480 for the CHAdeMO equipment.