Of course, you should! And do it as soon as you see he/she has logged in after a long time. Welcome them back and make sure to let them feel you are happy to see them on board again.
You can then ask if they need help and offer some tips on how to proceed by checking his VP ledger first and then direct him/her to do it. Then ask if it's okay if you send him another email with more tips, guides and direction.
