Slack had a pricing policy called “fair billing” where you add all your users but Slack only charges you for people that login. If you pay yearly and someone doesn’t log in after some sort of time, they credit your account. I loved the idea behind this and we copied it at one point.
It really failed us. I appreciate the spirit of the policy but the actual mechanics were confusing to people (“Why am I getting a credit for $0.33 on my bill?”) and made people angry (“I budgeted x for this tool, and your invoice isn’t x. This is making things difficult for me!”) and the accounting statements were impossible to read (“$2.40 credit for Jim because they are inactive. $3.76 charged for Sue because they became active”).
So it was very short lived and we switched away from it. We didn’t really consider the type of tool that Slack was, and what customer’s expectations were.
Another story: I remember Dropbox had a plan for like $15 for five users. You couldn’t buy less than 5 users though. If you had 4 ppl, you paid $15. If you had 2, you paid $15. The nice thing was this cut out a lot of noise that can happen when you look at logo churn for example, or count your customers, or other things where tiny teams or single user people can make the numbers look strange. It also can make things less expensive for small teams because then they don’t feel the additional cost of each user at first. But then at some point we talked to someone from Dropbox and they told us this was a huge mistake and they really wanted to make it per user or maybe 2 people for $10 because all the teams that were 1, 2, 3, or 4 people were annoyed that they had to “pay for 5 people when they were only 3”. Perception played a huge role in this not working for them. They thought the pricing was doing their users a favor, but it turned out it was working against them.