Mercenary
These Rogues are more rough and tumble than elegant. But they get results where others may fail. They are adept at taking advantage of every opportunity to get ahead. Some may say they lack loyalty, they would be wrong. Mercenaries are incredibly loyal. To themselves. A Mercenary could be hired with money. But they take all sorts of currency, information and favors can be just as lucrative. Their persuasive skills are legendary as they wheel and deal like no others. Their team skills are also second to none.
Subclass Features
Opportunist
Your quick thinking opens up opportunities that most wouldn’t see. You can make an attack of opportunity in the following additional circumstances as long as they are within your melee range: when a creature fails a saving throw, if a creature critically fails an attack, if the creature takes a critical hit from another source other than yourself, or if the creature takes on a status condition.
Supernatural Business Acumen
You are a businessperson like all Mercenaries and your skills are your wares. You have honed your persuasive skills to an unnatural degree. The first time you succeed a Persuasion check with a creature they must make a WIS check. On a failed saving throw they become Charmed for one minute. A creature Charmed this way views you favorably and is willing to cut generous deals such as discounts as much as 50%, doubling a payout for a job or similar business decisions (Your personal standing does effect this feature and the range of effects are determined by your DM, but will be favored as much as possible). If a creature succeeds the saving throw, they are Immune to its effects for 24 hours. Either way the creature is aware that they were swindled or you tried to swindle them.
You can use this feature once per long rest.
Tough it Out
You are tougher than most Rogues. When you take damage from an attack you can see you can reduce the damage by your CON modifier (Minimum 1) + your Rogue level using your reaction.
You can use this feature times per long rest equal to your CON modifier (Minimum 1).
Group Work
You are skilled at working with groups of skilled individuals. You can use the Help action as a bonus action. When you use a Cunning Action, you can use your action to apply the same action to up to six willing creatures you can see within 60 ft of you.
Betrayer
Betrayal is part of your life. You may not like it or you may in fact love it, either way it’s effective. If you successfully land a hit on a creature you Charmed that you have not dealt them damage before, that hit becomes a critical hit that applies your Sneak Attack damage + your Rogue level in damage.
If you successfully land a hit on a Charmed creature that was not Charmed by you, you still land a critical hit but do not apply the other bonuses.
You may use this feature times per long rest equal to your DEX modifier (Minimum 1).