How do you redesign pricing when tiers misalign with how users extract value?

We originally priced based on team size, but realized our product was heavily driven by individual daily usage instead. Watching users downgrade because the billing didn't match their work reality was a brutal wake-up call.

Transitioning tiers without alienating early adopter feels like performing surgery while blindfolded. For founders who have successfully restructured pricing: what indicators told you it was time to make the shift?