Yes, make a trigger brush entity around the spawn and make it a "trigger_add_tf_player_condition", then set the condition to (I'm not sure which) either
TF_COND_PARACHUTE_DEPLOYED
or
TF_COND_PARACHUTE_ACTIVE
My money is on the ACTIVE one, but try both just incase. Remember to use the console command "thirdperson" to see if you get the parachute model on the character's back.