But when I think of, say, $5000/year revenues, if it's too high, I have to fight the corporate financial immune system. But if it's too low, I'm leaving money on the table when there's a ceiling on how many customers can ultimately be acquired.
Pricing is not even on the list of concepts I have to consider to work through a process. I work for a very big company though.
The product scales outward thing is overrated. Startups have talked to me about this too, and it doesn't make as much sense as everyone seems to think.
You gain a foothold in an area in the company no one cares about, that doesn't mean anything. You are the least person to judge which parts of the company matter, so be careful about that idea.
I just had a company do this. They built a foothold in an area no one cares about. I had to tell them, it's about as meaningless as an organization if you had our janitors using their software.
If your evangelists are not connected and part of the decision making process, the information doesn't expand.
To expand on Andy's general point, and one josh2600 made earlier, it truly pays to get to know your target's corporate culture and bureaucracy. One of the first questions experienced sales reps ask at the close of the second call (or whenever the first demo is) is something along the lines of "what is your sales process like?" or "how does your department handle budgeting, and what is your fiscal calendar?"
Oooh, before I forget, here's another big turn-off: yes, sales reps hop between companies more than engineers, but for goodness sake PLEASE keep your CRM updated so your target doesn't get repetitive cold calls from other reps at your company. This doesn't happen too often, but I still experience it about once a quarter and it leaves me fuming each time, especially if I already have a contractual relationship with the vendor.
I wrote a blog post on how to figure out whether your startup is New Enterprise or Old Enterprise: http://brandonb.cc/is-your-b2b-startup-new-enterprise-or-old...
I think once you answer that core question, the pricing and sales model fall into place more easily.
If you're pitching SaaS to an industry that doesn't usually go for it, it sometimes it helps to avoid PII. Even banks are somewhat open to using SaaS for products that don't touch customer's names, transaction info, etc.
Be careful, though, self-hosted customers can be huge PITA's.