Pricing is psychological

What’s a better pricing strategy? $99.95 or $100?

It depends. If you’re selling to consumers the classic approach is to use $99.95, which looks so much cheaper than $100 and a bargain is a good thing. On the other hand if you’re selling to the enterprise using $99.95 seems cheap, unsophisticated, nickel-and-diming.

In the same vein, if you decide to use a non-standard way of pricing support (say price per system when the usual approach is pricing per user) you’ll want to check that your target customer will consider it future-thinking, not out-of -it. This doesn’t mean you must always follow the safe and boring path of imitating what your competitors are doing — but you must check that your approach is viewed as fresh, inventive, attractive rather than bizarre, far-fetched, and worrisome.