For this achievement you will need to deliver a bounty alive. A tip for this is to shoot them in the legs.
You will need to unlock Maude’s bounty missions before going for this achievement. She is unlocked after the mission MR Phillips.
She will appear as a strangers and freaks
Guide for the location of the bounty’s:
https://m.youtube.com/watch?v=kOXsgBbTtRY&pp=ygUaYWxsIG1...