[@Free Faller] Any chance that Laila and the Jackal recognize each other? They both have a background that seems like it'd have a cross section for the both of them at the Rogue Guilds. The difference being that Jackal was simply a contract thief, or fixer if you want to use slang, instead of being an official member of the guilds.

On a side note... the reason a Guild would hire a fixer is the security of a lack of information if that person is captured. So you'd send them into terribly high risk situations to set up a job for the guild members.