Base Class: Rogue
You channel your innate ability to lead and take a position as a commander and ruler. Warlords, iron-fisted rulers, and leaders of thieves' guilds may follow this archetype, as do charismatic generals and manipulative religious leaders. Your abilities revolve around directing your allies and intimidating your foes, and you operate at your best when you can rely on those who follow you.
Force of Personality
You gain proficiency in the Intimidation and Persuasion skills. You also gain expertise in these two skills provided you don’t already have expertise in each skill from another source.
“If you want a quality, act as if you already had it.” - William James
Natural Leader
Starting at 3rd level, you learn the basics of assuming a command position in a group. You can use the bonus action granted by your Cunning Action to issue a command to an allied creature within 30 feet of you that can see and hear you. It can then immediately use its reaction to make a weapon attack against a creature that you and it can see.
“If you lead the people with correctness, who will dare not be correct?” - Confucious
Dominate Person
Also starting at 3rd level, you begin to learn how to weave your words to increase your influence on those around you. As an action, you force a humanoid within 30 feet of you that can hear you and shares at least one language with you to make a Wisdom saving throw. The DC is 8 + your Charisma modifier + your proficiency bonus. On a failed save, the creature is charmed by you for 1 minute. While the creature is charmed by you in this way, you can use your action or bonus action to demand it follow an order you give it. The creature must then follow the order to the best of its ability provided the order does not place the creature in immediate harm.
The effect ends early if you or your allies attack the creature or force it to make a saving throw, or if you dismiss the effect, no action required. A creature doesn’t know that it was being influenced by magic, but a creature that would not follow listen to your orders otherwise knows that it was being manipulated.
Once you use this feature, you cannot use it again before finishing a long rest.
“He who wishes to lead must know how to command.” - Niccoló Machiavelli
Charismatic Fighter
By 9th level, you have found new ways to use your personality on the battlefield. You add your Charisma modifier (a minimum of zero) when calculating your initiative. In addition, you win all initiative ties.
“Winning isn’t enough. The acme of all skill is to defeat your opponent before going into battle.” - Sun Tzu
Lead by Example
Also by 9th level, you have proven to be a leader that fights alongside their troops. When you hit a creature with a weapon attack, the next attack roll against it made by a creature other than yourself has advantage.
“Leadership is the art of getting someone else to do something you want done because he wants to do it.” - Dwight D. Eisenhower
Tyrant's Enmity
Starting at 13th level, you learn how to channel your anger into your weapons. When an enemy creature damages you with a weapon attack or a spell effect, you can immediately use your reaction to make a number of weapon attacks equal to your Charisma modifier (a minimum of one) against that creature.
Immediately after you do so, you can force the creature to make a Wisdom saving throw with a DC of 8 + your proficiency bonus + your Charisma modifier. On a failure, the creature drops anything it is holding, becomes frightened until the end of its next turn, and must use that turn trying to get as far away as possible from you or, if it is unable to do so, using the Dodge action.
Once you use this feature, you cannot use it again before finishing a long rest.
“If a window of opportunity appears, don’t pull down the shade.” - Tom Peters
Turn the Tide
At 17th level, you become the pinnacle of a commander. As an action, you can use the persona you’ve built around yourself to change the tide of a battle, either by rallying your troops or by routing the enemy.
If you choose to rally your troops, you target all allied creatures within 120 feet of you that can see and hear you and share a language with you. All targeted creatures immediately gain temporary hit points equal to your rogue level + your Charisma modifier (minimum of 0), and for the next minute, all targeted creatures are immune to the frightened and charmed conditions and add your Charisma modifier (minimum of 0) to all Dexterity or Wisdom saving throws and attack rolls they make. In addition, when you use your bonus action granted by Natural Leader, you can target any number of creatures provided all of them are currently benefiting from this trait. The order to attack can either be specific (attack the Cloud Giant) or general (engage an enemy soldier) but must apply to all targeted creatures.
If you choose to rout the enemy, you target all hostile creatures of your choice within 120 feet of you that can see you. All targeted creatures must succeed on a Wisdom saving throw against 8 + your proficiency bonus + your Charisma modifier or be frightened of you for one minute. When a creature that is frightened in this way is hit by an attack made by you or one of your allies, it must succeed on another Wisdom saving throw or be forced to use its action on every subsequent turn it is frightened to move as far away from you as possible. When a creature ends its turn either greater than 200 feet away from you or out of direct line of sight of you, it can repeat the saving throw, ending the effect on itself on a success.
Regardless of the effect you choose, once you use this feature you cannot use it again until you finish a long rest.
“I am not afraid of an army of lions led by a sheep; I am afraid of an army of sheep led by a lion.” - Alexander the Great