Learning about our prices was easier through a support ticket than through spreadsheets

The customer wrote to ask why our plan down had not included the one thing she uses every day, and our plan up included six things that she would never use. She was not complaining. She was confused by whom we designed our plans for.

I had invested countless hours to make sure our pricing tiers were priced correctly, but zero effort into seeing if our pricing tiers told good stories about our different types of customers.

How did you determine your tier boundaries, based on usage, competitive mimicry or real-life dialog like this?