Patio11 had a sort of talk on this recently, but I'll recap what I think is perhaps the most relevant to this situation:<p>Start with 'small enterprise'. If you have even one smallish company that you can get in the door in, use that as a resume booster for a slightly larger company, and keep parlaying that success, each time seeking a slightly bigger customer than the one you just landed.<p>As ams6110 mentioned, don't expect a short sales cycle, and factor that into the cost of your product. Also, the sales process if VERY high touch. If it's an expensive product, expect to have to schmooze clients with dinner and repeated meetings with growing audiences. Don't mistake progressive meetings and schmoozing for progress. Do understand the cost of buying dinners and hiring sales people to chase one big customer for 6 months at a time with the expectation of not landing the customer.<p>Simply put, it's elephant hunting. You have to be very patient, invest in very expensive tools, and will likely come home empty with each expedition. This is also why Enterprise software tends to be so expensive, in that it has to recoup all the costs from failed sales on every successful sale.<p>Lastly, expect to be nickeled and dimed (especially if you're talking federal enterprise), and don't expect to be paid promptly.