Normally, CrewBuddy will be sending all your trips to PerDiemMax throughout the year.  However, you can easily force CrewBuddy to grab all your trips that are available from the server and send them to PerDiemMax.  Here's how:

Make sure you have a good internet connection before proceeding.

1) Tap Settings

2) Tap Advanced

3) Tap Force Send all trips to PDM

That's it!  After a few seconds, you'll get a confirmation that everything has finished.