You can't compete with $MEGACORP on fancy dinners, but you can compete on great products, which they generally suck hard at. Look at GitHub, who presumably hav

You can't compete with $MEGACORP on fancy dinners, but you can compete on great products, which they generally suck hard at. Look at GitHub, who presumably have giant enterprise accounts by now. But they started by making something great for hackers. While enterprises might seem like cold places devoid of humanity, a lot of people inside the enterprise want to get stuff done as much as anyone else. They will pay out of their own pocket and claim the cost as an expense later. They will fight internally to adopt products, etc. And once an app is used by a team, if it's good, it has the potential to spread virally inside the company. Other examples: Evernote (who just launched Evernote Business), Google Docs (the word processor came from Writely), Yammer, Atlassian's Confluence. I expect Trello is already used all over the enterprise and will be turning profits on that too.