Pros
Job descriptions are ambiguous enough that if you'd like to do something a little different you can. Makes for a fairly flexible career path. Upper management is amiable and can be very easy to talk to and get along with. There are a lot of people willing to help and support you. Great people work here and it can be a lot of fun.
Cons
Job descriptions are ambiguous enough that you are sometimes expected to do things that overextend what you would generally expect in your role, with little to no appreciation. Upper management does not reflect the ideals the CEO puts forward unless it's already in their nature - and for enough of them it's not. There are worthy people who get overlooked for promotion - this is partially because management doesn't always seem to know what to look for or what metrics to use and partially because of the social politics of the place. iPipeline is not alone in this element and it isn't rampant, but it happens enough to be a source of contention.