Ok so I'm not posting the spoiler, but someone else may…

Do you need 50 victories? Or jobs played?

And do you need 30 DIFFERENT awards or just 30 post job awards?

Because I have the cash, and have played about 70 combined different jobs…. just wondering if its one of those gaming achievements that you just play a bunch and it unlocks or if you can actually strategize for this. Thanks guys.

Overachiever
~Get over $2,500,000 cash in multiplayer, earn over 30 awards, complete 50 jobs successfully

It'll take a bit of time to do, you need to earn all your awards and complete 50 jobs with a victory. The fastest way to earn money is to play slime dunk, but if you want to keep it varied just play through numerous campaigns. You must get 30 different post job awards, and you must play all these games as ranked matches and these must be victories.

Well… I believe there are 44 post-job awards… so you just have to get 30 of them.