Most subscription revenue companies face a dilemma when deciding how to track opportunities in a CRM, because a lot of what determines how much the deal is actually worth depends on what happens months or years into the future. For example, a small win can turn into a very large customer if they upgrade. And vice versa, a very large win can be canceled in the next month if something goes wrong and you bill on a monthly basis.
But opportunities are meant to be marked as won or lost well before any of that happens. And since they are usually the basis for how much commission to pay in a month, it's important to get this right and be consistent.
Our general recommendation is to either track the incremental MRR or ARR that the deal represents at close. If there is a larger opportunity down the road (i.e. customer initially tries a pilot, then does a significant expansion), then track those as two separate opportunities.
If you bill annually, you can also consider comping on renewals, and you could even set up a separate pipeline to process those.