With the work permit request, you are able to get a Single Entry (90 days) visa.
Once got it, your work permit will be ready (after no more than 30 days) and you can apply the 1 year visa; by the way usually it is applied once the 90 days are going to expire.
You can cross the border at Satun and get 90 days on your proper visa.
If you need a 30 day stamp they consider your "passport story" (you cannot just finished a tourist visa, you cannot get a 7 day extension, etc) after that they give you 30 day stamp asking a fine of 1,000 baht.
Get a 30 day "visa exempt" stamp on arrival, then buy a 30 day extension at any Immigration office inside Thailand (1,900 baht) and you are covered for 60 days