I think Herkimer is the one that is behind the video game being made about her character. He is the one that framed Chloe for treason and got her executed in her past life. He is probably in the real world too.
That women that came to Chloe in prison is either the female coworker or the boss. Chloe described her as "warm and bright, like the sun. Pure and radiant. You were just too dazzling, I couldn't stand you." Based on Chloe's description, the boss is a better fit. But, the boss has acted totally confused by Chloe's behavior. The female coworker acts far less confused by the way Chloe acts. So she has a stronger case for being a reincarnate, and keeping it secret. So she can support Chloe in her new life. Either way, the author is playing their cards close to their chest.
I like that we're getting to see a better side of that one coworker with the glasses. Chloe has had nothing but bad interactions with him up to this point. But he felt sympathy for Chloe, and went out of his way to setup a group outing and invite her. As an introvert, I love people that do this, and drag me to outings, where I resist initially. I usually end up having a good time.