If you want him to run/jog/walk to the plane first of all he needs to be outside of it.
but first of all
Setup a Pilot, Plane, 1 Trigger, 1 or More EIs (Enemies)
-Set the Trigger with this (needs to have a radius).
1-Activation "OPFOR" (or who's your Enemy)
2-Detected by "BLUFOR" (or who's your Faction)
Leave the Trigger.
marker* = waypoint
1-Make a move marker for the pilot
2-Make a get in marker
3-Sync the Trigger (Sync not group) to the Move Marker (if the Pilot it's far away from the plane i recomend do a Move marker beside the Pilot, then put another move maker close to the plane then a get in, AI will move to the sync one.
4-Make the Pilot or any Friendlies inside the trigger spot the within, Enemy units.
P.S: I know the pictures are from A3, that's why i said like was A2, it works the same but A3 it's more user friendly, if you're still having issues or u didn't understand from the text u can add me and i can show you visualy Here