Once a prospect is clearly in your "Enterprise tier" and you enter into custom pricing, how do you gauge what the correct price to quote them is. Or rather, their willingness to pay? What questions do you ask? What do you do when you feel you've quoted them too high?
An "enterprise tier" price usually means there are multiple people involved in the buying decision, and a structured buying process. You can use this to your advantage:
You can usually use these kinds of datapoints to construct a price that the internal champion can get behind, that fits at the appropriate level for purchasing approval, and (ideally) fits within the customer's budget.
I think that this is tricky. It depends a lot on your industry. I think the most valuable data to inform these prices are reactions and opinions from people who are in your target market. I would recommend finding a mentor in that target market, someone who can help shape the type of business you are creating and you can talk with honestly and openly. I realize that is hard! The other option is to conduct interviews, do competitive pricing, etc. I have done a combination of the two to inform my own projects' rates. When you have quoted too high, I think it will be obvious in your conversation (and uncomfortably so). In my opinion, you can't back down once you've quoted, that's why its best to talk to mentors first if you can. Good luck!