Build Enterprise Applications for the Employees, Not Managers

If you design it for the employees, I'm not sure it qualifies as "Enterprise" software any more. Not that that's a bad thing.

Individual employees of a large organization are the very definition of a hard sale. Several hurdles come to mind:

1. Very few people are self-starters to the degree that they'll learn new software voluntarily.

2. It's rare to find anyone willing to spend their own money on something that isn't going to generate an immediate return, and non-managers don't have authority to expense much.

3. Many large companies prohibit installing unapproved software, and get really antsy if anything proprietary leaves the corporate network.

I suspect you'd have more success targeting business applications at self-employed and small business users. There's always been a healthy market for financial and legal products servicing people who don't have the money to waste on 'enterprisey' software.