To pop this one you'll need to be the heist leader of any heist after your first attempt at "The Fleeca Job".
The quickest, easiest, and cheapest way I've found to do this is to simply call Lester once you've finished the first heist (you many need to wait up to an hour real-time) and request to replay the same heist. It'll only cost you $11,500 and you only need one other person.
The achievement should pop as soon as you start the heist.