A large part of the implementation can be prepared from Canada within his existing employment, which usually removes the pressure from the immigration timeline.
Split remote preparation from on-site work
Configuration, data mapping, documentation and remote testing can generally be done by an employee working in Canada for the Canadian employer, and none of that requires United States work authorization. What requires presence is the on-site cutover, hands-on training and the period of supervision afterwards. Planning the project in those two halves usually shows that the date the affiliate cares about is achievable even if adjudication takes longer than hoped. It also removes the temptation to send him for a few weeks on a visitor basis to perform the work, which is a materially worse problem than a delayed cutover and is difficult to explain in any later application. Set the project plan around the two halves and the pressure on the filing largely disappears.
Hypothetical example: A food-packaging company schedules a three-day shutdown to install its internal quality-control workflow. The first review should identify which preparation can be completed from Canada, which tasks require United States presence, and how much specialized-knowledge time remains. The signed implementation plan settles the critical date. If the remaining classification time cannot cover the work and follow-up, the company needs another lawful staffing plan; sending the employee temporarily as a visitor to perform installation is not a solution.