In order to obtain this achievement, you will need to complete three different challenges for The Doomsday Heist. You can check your progress at any time by pressing and going to STATS > Awards > The Doomsday Heist. The challenges in question are:

Criminal Mastermind II: Complete The Doomsday Heist in order, with the same team of 2 players, on hard, difficulty, without losing any lives on Setups and Finales.

Criminal Mastermind III: Complete The Doomsday Heist in order, with the same team of 3 players, on hard, difficulty, without losing any lives on Setups and Finales.

Criminal Mastermind IV: Complete The Doomsday Heist in order, with the same team of 4 players, on hard, difficulty, without losing any lives on Setups and Finales.

Continue reading below for additional guidelines, strategies, and tips involved with this achievement.

Key Tips, Guidelines, and Notes

• Prep missions can only be done in public lobbies, while Setups and Finales can be done in Private lobbies
• You can die during Prep missions
• You cannot purchase Prep equipment/vehicles or utilize the "Trip Skip" option during missions as it will void challenge progress
• You can fail a Setup or Finale (and restart by using the "Quick Restart" option) but it cannot be due to a death
• You can call Lester and remove your Wanted Level during Prep missions
• Using an Armored Kuruma during Prep and Setups missions is highly recommended
• Buy full ammo and full Super Heavy Body Armor before every Setup and Finale
• Stock on free snacks inside the Facility before every Setup and Finale
• When eating snacks for health regeneration, do so in cover as it cancels the animation of eating the food
• Make sure to eat snacks and apply body armor mid-mission through the Interaction Menu

All in all, these three challenges willprove to be difficult, but with enough practice and with a good group of teammates, each challenge should be manageable within a handful of hours (the only overly difficult one is Criminal Mastermind II, as some mission objectives are seemingly impossible with just two players).

As a final note, make sure you are checking your Challenge progress after each and every Prep, Setup, and Finale. There have been some reports that the Challenges often reset themselves (for reasons unknown), so checking your status periodically is a good way to make sure you are staying on track.

Once all three of the new Criminal Mastermind Challenges have been completed, this achievement will finally unlock.

A step-by-step guide/walkthrough of this entire DLC, courtesy of user Neg96, can be found HERE. It is extremely detailed, and should provide all of the information needed to finish this heist.