Confirm the affiliate is operating, appoint a manager for the Paradise company, paper his U.S. appointment and employment, file the petition, then apply for admission with the approval notice. Do not start running the affiliate from the United States before the approval.
Set the Canadian side up first, then file
The order protects both companies. First, gather two years of the affiliate's operating records and confirm they show an active business; if they do not, the petition becomes a new-office case and the plan changes. Second, appoint and document the person who will run the Paradise consultancy, because the petition must show the Canadian entity continues after he leaves and because clients will ask.
Third, have the affiliate's board pass the resolution and issue the employment agreement so the U.S. employer relationship exists on paper before the filing date. Fourth, file Form I-129 with premium processing if the affiliate's contracts need him promptly.
Fifth, apply for admission at a port of entry with the approval notice; Canadian citizens do not need a consular visa for L-1. Throughout, keep an accurate record of days spent in the United States, since managing the affiliate from its office before approval is unauthorized work and days spent there do not count toward the qualifying year. The family's L-2 applications follow his admission or accompany it.