Been there, done that. I can tell you that - as a startup - it's next to impossible to make a deal before you run out of money. With enterprise customers it ta

Been there, done that. I can tell you that - as a startup - it's next to impossible to make a deal before you run out of money. With enterprise customers it takes at least several months from the first sales pitch to striking a deal. There are one or two startups though which managed to pull this off. Atlassian comes to mind. That being said, from currently freelancing in enterprise software development once more (sadly, bills have to be paid ...) there are lots of pain points in enterprise IT environments. Enterprise IT basically is lacking in every respect. Time tracking, ERP, CRM, ticket management, document management, I can hardly think of any area enterprise IT isn't light years behind what I'm normally used to. Problem is, there already are tons of better products for each of those areas. Tragically, once they've made a purchase decision enterprise customers are highly unlikely to switch to a different product, no matter how much better it is. This is the reason why the likes of Oracle, IBM and SAP are so formidable at selling their crappy software and it's also the reason why I currently have to put up with an HP issue tracking system that actually requires IE6 to run and is so far behind any other issue tracking system out there, - free or not.