Sidekick: Expert

The expert is a master of certain tasks or knowledge. This sidekick follows a path that favors cunning over brawn or spellcasting. It might be a scout, a musician, a librarian, a clever street kid, a wily merchant, or a burglar.

To gain the expert class, a creature must have at least one language in its stat block that it can speak.

A sidekick gains the following class features as it gains levels in this class, as summarized on the Expert table:

The Expert

Level	Proficiency Bonus	Features
1st	+2	Bonus Proficiencies, Expertise, Helpful
2nd	+2	Cunning Action
3rd	+2	Jack of Many Trades
4th	+2	Ability Score Improvement
5th	+3	Extra Attack
6th	+3	Expertise
7th	+3	Evasion
8th	+3	Ability Score Improvement
9th	+4	Inspiring Help (1d6)
10th	+4	Ability Score Improvement
11th	+4	Reliable Talent
12th	+4	Ability Score Improvement
13th	+5	Bonus Proficiencies
14th	+5	Ability Score Improvement
15th	+5	Sharp Mind
16th	+5	Ability Score Improvement
17th	+6	Expertise
18th	+6	Inspiring Help (2d6)
19th	+6	Ability Score Improvement
20th	+6	Stroke of Luck

Bonus Proficiencies

At 1st level, the sidekick gains proficiency in one saving throw of your choice: Dexterity, Intelligence, or Charisma.

In addition, the sidekick gains proficiency in five skills of your choice. If the sidekick is a humanoid, it also gains proficiency with light armor, simple weapons, and two tools of your choice.

At 13th level, the sidekick gains proficiency in one skill of your choice. If the sidekick is a humanoid, it also gains proficiency with one tool of your choice.

Expertise

At 1st level, choose two of the sidekick's skill proficiencies. The sidekick's proficiency bonus is doubled for any ability check it makes that uses either of the chosen proficiencies.

At 6th level and again at 17th level, choose two more of the sidekick's skill proficiencies to gain this benefit.

Helpful

The sidekick is adept at giving well-timed assistance; the sidekick can take the Help action as a bonus action.

Cunning Action

Starting at 2nd level, the sidekick's agility or quick thinking allows it to act speedily. On its turn in combat, it can take the Dash, Disengage, or Hide action as a bonus action.

Jack of Many Trades

Beginning at 3rd level, the sidekick can add half its proficiency bonus to any ability check it makes that uses a skill but doesn't already include its proficiency bonus.

Ability Score Improvement

At 4th level and again at 8th, 10th, 12th, 14th, 16th, and 19th level, the sidekick increases one ability score of your choice by 2, or the sidekick increases two ability scores of your choice by 1. The sidekick can't increase an ability score above 20 using this feature.

Extra Attack

Starting at 5th level, the sidekick can attack twice, instead of once, whenever it takes the Attack action on its turn.

Evasion

Beginning at 7th level, because of extraordinary good luck, the sidekick is skilled at avoiding certain dangers. When the sidekick is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, it instead takes no damage if it succeeds on the saving throw, and only half damage if it failed. The sidekick doesn't benefit from this feature while incapacitated.

Inspiring Help

Starting at 9th level, the sidekick's assistance becomes especially inspiring. When the sidekick uses its Helpful bonus action, the creature who receives the help also gains a 1d6 bonus to the d20 roll. If that roll is an attack roll, the creature can forgo adding the bonus to it, and then if the attack hits, the creature can add the bonus to the attack's damage roll against one target.

At 18th level, the bonus increases to 2d6.

Reliable Talent

By 11th level, the sidekick has refined its skills to an exceptional degree. Whenever the sidekick makes an ability check that includes its whole proficiency bonus, it can treat a d20 roll of 9 or lower as a 10.

Sharp Mind

At 15th level, the sidekick gains proficiency in Intelligence, Wisdom, or Charisma saving throws (your choice).

Stroke of Luck

At 20th level, the sidekick has an uncanny knack for turning failure into success. If the sidekick's attack misses a target within range, it can turn the miss into a hit. Alternatively, if it fails an ability check, it can treat the d20 roll as a 20. Once it uses this feature, the sidekick can't use it again until it finishes a short or long rest.