Captain’s Orders
At level 2 you've either inspired, gaslit or intimidated your subordinates into compliance. Choose either persuasion, deception, or intimidation you gain proficiency in the chosen skill if you are already proficient you gain expertise instead. A number of times equal to half your proficiency bonus rounded up per long rest when your follower would make a damage roll you may make a check of the skill you choose and add half the result rounded up to the damage amount.
Act of Piracy
Your follower has learned a thing or two from you. At level 7 when you use your Captains Order’s feature your follower can attempt to shove the creature. The target that took damage from Captain’s Orders must make a Strength Saving Throw versus your Command Save DC or either be shoved 15 ft in any direction or be knocked prone.
Yo Ho Ho
Your leadership has developed to the point where you and your followers are able to exude an aura of personality. At level 13 as an action on your or your follower's turns you can unleash your pirate vibes. A number of allied creature's equal to half your proficiency bonus rounded up gain a 1d8 which can be used on an Attack Roll, Saving Throw or Skill Check. This die lasts until the end of initiative and does not stack.
Scallywagging
You and your crew are able to pull of mischievous stunts during combat. At level 17, twice per short rest, if you and your follower are within 30 ft and on opposite sides of a creature your follower can make a single weapon attack at the creature. If the attack lands the creature is pushed any distance towards (up to your location). Your next attack roll on this turn has advantage on its roll and deals an extra 2d10 of the same damage type as the attack.