I predict 2 outcomes,
This new maid is either:
1. a super masochist who WANTS to get severely punished by Jelly
or
2. a spy sent by someone else (someone like that narcissistic saint) who doesn't believe the rumors that Jelly has changed and wants to expose her for the horrible person she used to be.
This is my guess.
As seen in this chapter, she is clumsy by nature. One day, while she was working, she created a big mess that she couldn't compensated on her own. As an alternative punishment, she was sent to work under Jelly and tasked to get "punished" by Jelly, so her previous boss could get some sort of leverage.
That, or like Will, someone offer her something she can't refuse to go to work under Jelly and get "punished" by her while working there.
Obviously, being sent to work under someone who uses torture as punishment is stressful, hence the dark circle.
I also think she isn't a masochist, as seen on page 5, where she seems to feel pain after falling headfirst onto the floor. And each time she got rejected, what she showed was not dejection of being denied, but closer to desperation and bewilderment. At least that's what I get from reading it.