Only if the transferee already meets the one-year employee test and the US role is already managerial. Premium processing can shorten the USCIS decision, but it cannot shorten a qualifying year that is still running, and a retirement date is not an immigration deadline.
Sequence the handover around the petition, not the other way round
The common failure is to treat the retirement as fixed and compress everything else. Start by checking whether the twelve-month employee year is complete; if it finishes in two months, the petition cannot be filed until then, and the retiring manager should be asked to stay on part-time or a US employee should act in the interim. Next confirm the subsidiary's staffing supports a managerial role; if it does not, hire before filing.
Once the file is ready, premium processing gives a fast USCIS decision, and a Canadian citizen can then present the approval at a port of entry rather than waiting for a consular appointment. Build in a few weeks for a possible request for evidence. Handover work that can be done from Canada, such as reviewing contracts, meeting distributors by video and planning the service schedule, does not require US work authorization; short trips to observe as a business visitor may be possible, but managing the subsidiary from inside the United States before approval is not.