There is also a similar story for Siebel (Northwestern Mutual I think?). In enterprise software, buying from small companies is not the norm, so if some large organizations invest in your product, it can trigger the larger market to believe in you. I believe the trick is to make sure the "big" accounts you take on aren't ones that are going to take you too far off your normally planned roadmap. If you find yourself building one-off features, one for each customer, you are in for a world of hurt. If your big customers drive you to build your roadmap faster or more aggressively, that isn't always a bad thing.

Yeah, but that's both the defense market (very unlike regular market) and the CIA (In-Q-Tel is unlike defense market). Quite an outlier that tells you nothing about the topic unless we're specifically trying to make that one, big customer be an organization that drops boatloads of money on unproven suppliers with a VC arm looking for them. In-Q-Tel is cool in that they've done this for a number of firms with great products. They're just really, really different from the norm.