Infiltrate

You are the ultimate stealth assassin, infiltrating the heart of the enemy ranks.

Level 3: Prologue

Quick Draw. You gain advantage on your initiative rolls. In addition, during the first round of combat, the first attack roll you make against a creature that has not taken a turn yet has advantage.

Weak point  You look for your enemy's weaknesses. You can use Study in a Bonus Action. An enemy studied must roll Deception to cover their weakness, while you must roll Investigation. If you roll more than them, Until the end of your next turn, your attacks against the target can trigger Sneak Attack even if you don't have advantage, provided no other disadvantage applies.

Level 3: Derive

You can choose to specialize in one of the following tools: Forgery Kit, Disguise Kit.

In addition, you will gain proficiency in one of the following skills of your choice: Arcana, Insight, Investigation, Perception. 

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Level 9: Open wound

Open wound (cost2d6) When you perform a Sneak Attack on a creature, you can waive 2d6 of Sneak Attack damage to reveal the target's weak point. Until the beginning of your next turn, the next attack by an allied creature on that creature will deal an additional 1d6 damage.

Level 13: Mindstone

You gain proficiency in Wisdom and Charisma saving throws.

Level 17: Never Miss

Once in combat, you can reroll the D20 dice.

When you roll Sneak Attack damage, you can reroll a number of the Sneak Attack damage dice up to your Intelligence modifier (minimum of one). You must use the new rolls.

You can use this feature a number of times equal to your Intelligence modifier, regaining all expended uses when you finish a long rest.