You served as a spy in for thieves' guild. You were trained in the art of espionage to be an undercover agent or a plant. Two-faced, duplicitous, cunning, you do what it takes to get the information you need and survive. You very likely don't have a life outside of your job. You eat, breathe, and sleep your fake life until it's time to be done completely. Then its a little bit of rest and recovery until your next long con.

Or

You served as a lookout in a thieves' guild. You were trained to be the eyes for a heist, watchman for a black market deal, or the dealer in an underground gambling den. Your eyes and ears are your business, and you almost always worked as part of a crew where you were the only lookout. Your life was pretty normal, and although you've seen somethings, you probably never had to do them.

Skill Proficiencies: Choose either to gain proficiency in Stealth and Perception or Insight and Deception.

Languages: You can speak, write, and sign in Thieves' Cant.

Equipment: A set of common clothes (hooded), a set of silk clothes, a secret about a local noble, and a pouch containing 30 gp

Suggested Characteristics

Be creative.