To get this achievement it very easy....All you must do is with each one of the riders from the SSX team (NOT Griff), ride with all 3 of the helicopter pilots.
TEAM SSX:
Zoe
Elise
Mac
Alex
Tane
Kaori
Psymon
Moby
Ty
Now...The 3 ranges that I did the achievement were the Rockies( Aussie Pilot), Siberia( a woman), the Alpes( Russian Man).....
EXAMPLE: Pick Zoe as your rider, the Rockies as the range you want to ride, any kind of drop will do( u dont have to earn a medal to obtain the avhievement)...and thats it....do the same for Zoe with each other pilot....
Rinse and repeat with each rider and it will pop