Shadow Operative

Your life has always been full of conflict and excitement, because you made a living tracking down people for pay. Unlike some people who collect bounties, though, you aren't a savage who follows quarry into or through the wilderness. You're involved in a lucrative trade, in great metropolitan cities, that routinely tests your skills and survival instincts. More importantly, unlike a bounty hunter in the wild, you routinely interact with both the criminal subculture and other bounty hunters, maintaining contacts in both areas to help you succeed.

You might be a cunning thief-catcher, prowling the rooftops to catch one of the myriad burglars of the city. Perhaps you are someone who has your ear to the street, aware of the doings of thieves' guilds and street gangs. You might be a "velvet mask" bounty hunter, one who blends in with high society and noble circles in order to catch the criminals that prey on the rich, whether pickpockets or con artists. The community where you operated could be any city  that's large enough to have a steady supply of potential quarries.

As a member of an adventuring party, you might find it more difficult to pursue a personal agenda that doesn't fit with the group's objectives — but on the other hand, you can take down much more formidable targets with the help of your companions.

From your interactions with the local criminal society you have peaked up Thieves' Cant

Ability Scores: Dexterity, Wisdom, Charisma

Feat: Alert or Skilled

Skill Proficiencies: Choose two from among Deception, Insight, Persuasion, and Stealth

Tool Proficiencies: Thieves’ Tools or Disguise Kit

Languages: Thieves' Cant

Equipment: Choose A or B: (A) 2 Daggers, Thieves' Tools, Ball Bearings, Bedroll, 2 Pouches, Traveler’s Clothes, 16 GP; or (B) 2 Daggers, Disguise Kit, Gaming Set (any), Backpack, 2 Pouches, 1 Flask, Traveler’s Clothes, 16 GP; or (C) 50 GP