If you are going to parachute for the first time, you will be assured of the help of someone with long experience. The same is true when you have large, important IT projects that MUST succeed: You want advice from someone who has met most challenges before.
Coincidentally, Siri has experience as both a parachute instructor and project manager. She is thus our foremost expert in landing on her feet. (She primarily takes on assignments as project manager, that is.)