Been dealing with this mess for months now. Have users spread across three different pricing tiers from before our restructure.
Keeping everyone happy but it’s becoming a nightmare to manage. Support tickets are confusing, billing is complex.
Wondering how others handled the transition without massive churn.
Just bite the bullet and migrate them already.
Give users 90 days notice and migrate them over. Throw in a small incentive for early switchers. Most people get it when you explain the value properly. The ones who bail probably weren’t worth keeping anyway. Running three billing systems costs way more than losing a few users. Your team’s time is better spent elsewhere than babying legacy accounts.
Did this exact thing with a productivity app two years back. Had four legacy plans running alongside the new ones.
We picked the cohort with the highest LTV and gave them a custom migration path - let them keep their grandfathered rate but moved them to new features. Lost maybe 8% but kept the valuable users happy.
For the other cohorts, we ripped the band-aid off with 60 days notice. Sent three emails explaining why the change benefits them. Churn was around 15% but our unit economics improved by 30%.
The admin overhead of managing multiple plans was killing us. Once we simplified, onboarding new team members got way easier and billing errors dropped to almost zero.
Don’t overthink it. Users who really get value from your product will adapt. The ones looking for reasons to leave were probably going to churn anyway.
Move users over sooner rather than later. Waiting just creates bigger headaches down the road.