Any city has its share of secrets. Those secrets are valuable, so there are organizations who find those secrets and sell them.
What better place to both learn secrets and sell them than a tavern?
The Nightbird Tavern is a watering hole that locals have been coming to for generations. Its staff have been serving those same locals for generations, with sons and daughters taking over for mothers and fathers for as long as anyone can remember. Given their high standards of service, this surprises some foreigners, but it’s like the little ones are born for it. Turns out, they are.
Unbeknownst to anyone, the entire extended family that runs the Nightbird Tavern also make up the Raven Society, a tight-knit crew of spies who slip into alleys and listen behind doorways throughout the city. Because who would be surprised to see a scullery maid out on an errand in an alley?
Highly adept in combat, they train their children from the earliest ages in both spycraft and martial arts.
The clan is led by Matreya Ravenclaw, a battleaxe of an old woman who can be annoyingly stubborn or laughingly easygoing, with little in-between. Her second-in-command, Nisha, is a tall, taciturn master of combat.
As a friendly faction, the Raven Society operates as a neutral information broker, passing tips about upcoming monster attacks or cults on the move to the city watch. They charge reasonable fees for their information, with a hefty discount to good adventurers who publicly protect their city.
The Ravenclaws would be willing to pay–in gold or information–an adventuring party who can create an armed distraction while one of their members performs a little skullduggery.
As a foe faction, the Raven Society sells their information to the highest bidder and don’t care who gets hurt in the process. Too many factions rely on their services for anyone to risk taking them out. If threatened, they can call in favors from both law enforcement and the city’s underbelly.
Worse, Nisha has begun consolidating the family’s power in ways that are far less neutral than the past, calling in favors to eliminate rival factions in the city. Nobody in the Raven Society gets their hands dirty, of course, but bodies are beginning to pile up. Matreya is uneasy about this; either she or Nisha could hire the PCs to wipe out the other.