You made a living as a contract killer. There are many paths that can lead to such dark places, but few are skilled enough to avoid capture...or worse. You've learned to quietly strike from the shadows, to know the locale like the back of your hand, and if required, make your quarry trust you completely.
Skills: Bluff, Geographic Lore, and Stealth
Trait—Assassins Guild: When you are in an area of civilization, you can check in with the guild to obtain contracts to waiting to be fulfilled. The guild can give you information about your target, including their whereabouts and habits. Usually this
comes in the form of contacts who work with the guild.
Suggested Equipment: Cloak, mask, 6 daggers, shortsword, notes on target.
Assassin Rogue Scheme
Level 1: Assassination. Assassins are make a living out of removing their targets. Permanently.
Benefit: You have an additional way to deal Sneak Attack damage, besides having advantage against a creature. If you hit a creature with a melee attack and your target is a minimum of 20 feet from any other creature, you can deal Sneak Attack damage.
Level 2: Extermination. Everything has a weak spot, and your paid to know where they are.
Benefit: You have advantage on coup de grace attack rolls.
Level 5: Depredation. Your onslaught will not allow your quarry to leave your grasp.
Benefit: When you deal Sneak Attack damage to a creature, your target cannot take the disengage action until the end of your next turn.