Open the licensing file first, because third-party verifications run on schedules nobody in the process controls. The TN step can be prepared in parallel, but tie the employer's start date to the slower track rather than to an optimistic estimate of either.
Let institutional response times set the calendar
Regulators often wait on transcripts or confirmations sent directly by universities and other licensing bodies, and the applicant cannot accelerate those requests. Ask the regulator what remains outstanding, then work backwards to a defensible start date. If the employer needs someone sooner, raise that with counsel before agreeing to any interim arrangement, since duties performed in the meantime affect the profession being claimed.
The sequence that avoids repeat work is confirmation first, then a written duty description, then counsel review, then any application or admission attempt. A licence application can require verification from an institution or a home-jurisdiction regulator, and those third parties set their own turnaround. Identify what changed in the employer, duties, duration or compensation. Place the principal's admission period next to the program's start, term breaks, and expected completion. For a Canadian, the procedural choices generally include applying for TN admission at a port of entry or having an employer file Form I-129.