This achievement requires that you kill a Power Loader enemy with the Exit Strategist skill.
Exit Strategist is a skill that makes your dodge roll cause environmental items such as desks and tables to explode after you roll out from under them. The Power Loader is a large mech with a drill arm enemy type that can be found in the third dungeon, StyxCoin. On a run of this dungeon where you have the Exit Strategist skill, simply kill a Power Loader by rolling under its legs repeatedly, causing it to explode and the achievement to pop.
A couple tips to hopefully make this easier:
1. Once you've unlocked Exit Strategist, I would recommend leveling it up so you can equip it as your pinned skill when you want to attempt this achievement, negating the RNG challenge of it entirely.
2. Story/progression spoiler: