I work at a hedge fund. In the front office of a smaller shop, but I am pretty sure I know both firms you interviewed with. First off, congrats on both offers,

I work at a hedge fund. In the front office of a smaller shop, but I am pretty sure I know both firms you interviewed with. First off, congrats on both offers, these are not easy interviews or easy jobs to get. My 2 cents: Try to find someone doing the work you are about to do at the HF and have a conversation with them. I don't see any comment on here yet from someone who can speak from experience at a HF BO. That's a worthwhile coffee or phone call if you can find someone. Don't believe job descriptions, recruiters, or interviewers at the HF about what you will be doing day to day. Speak to someone who is a third party about the type of work in general (try Linkedin, Bloomberg, friends or whatever networks you are a part of to find someone to talk to). Ask them about the work, day to day, pros and cons, career progressions, lifestyle, etc... Second part of the answer. NYC and Chicago, and the two firms, are VERY different culturally. Think about what city you want to live in and what firm culture you prefer. I vote NYC over Chicago if you can. And then go for it, you have little to lose - if the work sounds interesting based on conversations with people actually doing it and the city is a place you wouldn't mind trying out living in, what are you worried about? You can always move back to SF or move to a different company, HF or startup in NYC. As for the vested options Q. You haven't given enough info for anyone on here to answer that prudently. Some people's sign on bonus will be negotiated to consider vested options at a previous job. Your offer looks standard and that you haven't negotiated anything on that part. Up to you if relevant, just sharing people do this. The HF is fully aware of what options are so you can bring it up with them if you choose. Congrats again.