SaaS going from free to paid. How to transition existing users?

Question

Long story short, our SaaS [0] has been free for a few years. We're now transitioning into paid plans.We've started charging new users and the conversion rate has been good. Now the question is, how do we transition our existing free users? There is a chance some people are gonna get pissed (even though they've been using our service for free).Are there any best practices on what to do in such a situation? The first thing that comes to mind is to offer a discount on the yearly plan. Anything else?[0] - https://lookastic.com

necovek · Accepted Answer

The best I can recommend is allow the free tier to move away their data locally (export): not sure if that makes sense in your context. That reduces the chances of them becoming pissed off (I always liked the distinction between British and US "pissed" though :)), even though it won't help with conversions much.
I don't think it's such a big deal anymore: users are already conditioned to expect entire free services to be gone tomorrow (somehow Google with Plus, Reader... comes to mind ;), so moving to being there but paid is not such a big deal.
Unless you promised it will be free forever (eg for beta testers etc).

ecohint · Answer

You can check episode E1088 of This Week in Startups for some ideas: https://www.youtube.com/watch?v=9OlrMNp90fc&t=1289s From 4:50 on the founder is taking about their transition from completely free to app with paid features.