The salesperson does not really rack up the dollar amount on a feature by feature basis. There is not some line item set of features each with a price. They are buying the whole thing - the feature dance is all about ensuring the customer (whether you have the goods or not) that your package will fit their needs. Large corporations have evolved themselves into a potpurri of rules and processes for how they do things. They dont make sense in most cases which is what prevents them from using a low barrier to entry tool like something a small startup might make - basically, they cannot change their process to fit the software, they need the software to fit them. None will, I repeat, no software from any vendor will fit their business...the salesperson has to convince them that you are the best company to make it fit.
Preferably dont hire guys and manage, hire no one and do it yourself. When you are working way too much, have not enough time and a mountain of work ahead AND signed deals with customers (including checks) then hire someone. Repeat this process. DO NOT HIRE people until you absolutely need them.
If the sales person is any good, he had the next lead before he left the last meeting. When you find a good one you will have to tell them to slow down.
Pricing is a black art, too low and no one takes you serious, too high and you become a budget item that needs to be planned for and the sales cycle goes on for over a year which gives competitors more chances. Feel out your customer, ask them directly what their budget is...but mostly let your sales person worry about that.