No killing without a cause.  No cause without a direction.  No direction without a payment.

All or nothing, a contract is binding.  The prey is already dead.

The Ring, called such because of the ring burned into your skin around the brand given to you when you joined the thieves guild, prides itself on its secrecy, and the fear that is associated with their shadowy guild.  As a true assassin, you've been conditioned to remain separate from your emotions, using reason and logic to accomplish the mission in whatever way you've been instructed.  Using the environment as your ally, with the help of deception and stealth, you will do whatever it takes to accomplish the will of your masters.  

Assassin Initiate

When you are chosen to become an assassin at 3rd level, your initial training gives you proficiency with the disguise kit and the poisoner’s kit. 

Arcane training also gives you the ability of Darkvision, out to a range of 30 feet.  If you already have Darkvision, the distance you can see is extended by 30 feet.

You also gain the ability to move along vertical surfaces and walls on your turn without falling during the move.  You have a climb speed equal to your walking speed, as long as there are handholds (cracks, protrusions, vines, etc.).

Quick to Kill

Starting at 3rd level, you have been taught to attack in the blink of an eye.  If you are using a finesse weapon in melee range, you can now draw your weapon and attack first, before initiative is rolled, giving you surprise and an advantage on your first attack.  It is at the beginning of combat where you are at your deadliest when your target is unaware of your presence, even on a battlefield full of allies and enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet, and a successful hit will be a critical hit.

Because of your heightened awareness, if you can see an enemy before they attack, you cannot be surprised by them in any way.

If you attempt to kill a target that is sleeping, or is stunned, blinded, incapacitated, paralyzed or unconscious, your first attack is made at advantage if a roll is required.  Your attack will cause damage equal to 6 times your class (rogue) level, in addition to critical damage caused by your weapon.

Master of Shadow

Starting at 9th level, you gain the ability to cast one of the following: Darkness, Disguise Self, Pass Without Trace, Silence or Blindness/Deafness.  You can cast each of these spells once, and recover all uses after completing a long rest.

You also have advantage on Charisma (deception) and Charisma (performance) checks when trying to pass yourself off as a different person.  You can mimic the speech of another person or the sounds made by other creatures that you have heard speaking or making sounds for at least 1 minute.  

Additionally, once per turn you can deal an additional 2d6 necrotic damage when you hit a creature with a weapon attack while that creature is in dim light or darkness.

One with Shadow

At 13th level, you become a shadow in the night, or like the clouds that pass overhead unnoticed.  You become an expert at stealth, if you are  not already.  In addition to this, you gain advantage on all DEX (Acrobatics & Stealth) ability checks that involve hiding, preventing detection, moving through spaces where others are looking for you, and avoiding capture when being pursued.   You also can use your Dexterity ability instead of Strength when attempting to escape a grapple condition.

You are also adept at evading creatures that rely on darkvision. While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

You also gain the ability to cast Arcane Eye.  The eye you create must remain in dimly lit or dark conditions.  A bright light will cause the eye to dissipate.  

Kill Move

Starting at 17th level, you have progressed into the inner circle of the Ring.  You have become a master of quickly killing your targets.  When you attack and hit a creature that is surprised or unaware of your attack, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the total damage of your attack against the creature.