I've just been listening to Aaron Levie of Box.com speak about how his team has been approaching working with enterprise software. One element stuck out to me in the context of building educational products. He said that his team has had a rule that if there's ever a choice to be made between meeting enterprise requirements and pleasing the end user, they've prioritized the end user, even if it meant turning down millions of dollars:
http://www.youtube.com/watch?v=qRt7mFuKwQY&t=39m49s
This addresses one of my biggest concerns with the idea of working with schools or governments as opposed to individual families. If you optimize for someone who isn't the end user, you end up gradually with a crummy product that focuses on the wrong thing. But with a web-based system, you naturally have a direct connection with the end user. You can see how engaged they are. You can see what they're spending time on and what's working and not. So maybe now it's possible to make an end run around optimizing your product for the wrong thing will still selling at an enterprise level.
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