I have been on both sides of the enterprise software sale many times and have concluded that a) it always sucks and b) it’s rarely in “anyone’s” best interest.
So instead of examining the current model and making suggestions for accomodating or improving it, I prefer to suggest an alternative.
I believe the best way to crack the enterprise software market is the same way to eat an elephant: one bite at a time through the soft underbelly…
Find a critical business function being done in Excel and provide an alternative web app.
Find a “business within a business” and automate it with modern technology. (Examples are small independent business units, warehouses, job shops, sample shops, “anything” a user has set up that “can” be autonomous.)
Provide a modern satellite system to augment and integrate with an existing enterprise monster. (A separate module for one function like payroll or fixed assets, special processes for marketing, engineering, manufacturing, etc.) The possibilities are endless. “Somebody” is not getting what they need out of SAP, Oracle, or whatever.
Provide a separate business unit with everything they need. This may be cheaper than the customer adding more licenses to their ERP system.
The key to this approach is staying under corporate IT’s radar. The way to do that is by keeping your prices below your customer’s boss’s threshold.
How do I know this can work? Because it has, many times. I have implemented dozens of apps in enterprises that they thought they could never have because of the existing software and sales model.
And I remember history. At one time, IT departments were very threatened by PC’s. They challenged their ivory tower with a mainframe and dumb terminals. So users just bought their own PCs from their expense budgets and forced IT’s hand.
Lightning can strike twice. Users are once again tired of waiting 18 months for a fix and are ripe for a custom 37signals type of solution. Let the app rush begin.