[mcdoug]

Wow, this is one of the most helpful comments here. If I can ask for some details:

The CEO track sounds nice. I've done the middle management stuff before and was quite successful at it. In my last job I was heading up the software team for a software/hardware startup, as well as taking on partial management of the support team and the data entry team. I have been C-level at two companies but both were early stage when they went belly up so this is more a bullet point on a resume than something I can point to and say "look there it is". Currently I work for a small enough company that there isn't any more upwards mobility here. I am basically working as an individual contributor directly with clients. The projects are boring but the pay is good and the people I work with are excellent. How would you suggest making a leap from here to something bigger? I live in an area with lots of banks and insurance companies, but not much in the tech world.

On the finance side, again, how do you go about this? What kind of companies do you suggest and what jobs in them? Are hedge funds a good idea? Or do I need to commute to something like NYC and apply for something with a large investor? What qualifications should I focus on before jumping into this? Is mostly reliant on knowing the right people? Is it about technical knowledge of the subject? Or is it about impressing the right interviewer?

[jmchuster]

C-level at a startup is probably comparable to middle-manager at most companies, so like 10 reports. CEO track means you're in charge of like a hundred people minimum. You don't apply to jobs any more in the traditional sense. Companies hire executive placement firms to hire you. For your area, you probably need to find VPs from the big companies there and ask them about how their career path goes.

If you want to get rich in finance go to Harvard and get your MBA, and then just follow what everyone else around you in your class is doing.