Work backward from the launch: evidence collection takes the longest, a port-of-entry application can be decided the same day, and an I-129 petition adds weeks. Choose the route only once the experience file is complete.
Build the evidence before choosing the fast route
Hypothetical example: the Vermont apparel company wants its new designer in place six weeks before the fall catalogue ships. Six weeks sounds sufficient until the timeline is laid out. Client letters from a lodge group and a bike-park operator take two to three weeks to obtain over the summer; translations add another week; the DEC transcript has to be ordered from the college.
Only then can the route be chosen. If the experience file is strong and the offer letter is clean, a port-of-entry application at a preclearance location or land border can produce a decision the same day, leaving the employer's start date intact. If any element is soft, an I-129 petition with premium processing trades money for a written record and a reviewable decision, at the cost of a later start.
Book nothing irreversible, including a lease in Vermont, until the route is decided, and tell the employer that the date is a target contingent on admission rather than a promise.