Been handling different pricing tiers for ages. It’s like a puzzle with three groups, all paying varied rates for similar features.
Support is overwhelmed, billing issues are piling up, and new customers are confused about their costs.
How long did you hold off before making changes?
Switched after a year. I was spending more time on admin than I made from those old plans.
Sent emails explaining the changes with 60 days notice. Offered to keep current rates for 6 more months if they upgraded. Most people got it, and the few who left weren’t worth the headache anyway.
Two years max then rip the bandaid off
Migrate everyone when support costs start eating your grandfathered revenue. Give 90 days notice with a small discount or bonus feature. Most users get it if you’re upfront about business needs. Running three pricing structures creates three times the operational headache. After 18 months, the complexity usually costs more than keeping old customers happy.