The Red Queen
The top boss in the guild is Mascy Jackwil, a female human who got her start as a con-woman running cons against adventurers on the trail. Those who follow her tend to be very dedicated and loyal.
The guild itself is a relatively structured guild, not like some thieves guilds that are just “go steal things on your own”. The guild is split 3 main section, thieves, assassins, and administrators. The administrators are the people who find the jobs or opportunities. They hang out in taverns do all of your typical “shady criminal” stuff and get someone to hire them. They then report back to the appropriate group and give them the job to be completed. And afterwards the administrator goes back to his contact to finish the job. The whole time the customer never even knows he contracted the Grey Daggers. Each of the sections is organized into regions under regional directors and then seniority, a veteran thief may be in charge of planning jobs/heists for a group of up to 7 apprentice thiefs, and the same goes for the assassins. These group leaders report to the regional directors who report to Mascy.
Tobbin is one of these senior thieves who has his own group of 4 apprentices under him. However they are all currently on an assignment and aren’t expected back for some time. This is part of the reason he was chosen for this specific job. The regional director that Tobbin reports to is named Thias Gilimore, a male elf cat-burglar.