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.