I've got a subscription service with a free tier. Initially, the free tier was far too generous. We've since significantly lowered what that free tier provides. However, we had grandfathered in people already on the free tier.
What are some strategies for moving people from a free to a paid tier, when the two tiers are nearly identical for these users?
I'm looking for some more creative solutions than simply ending the grandfathering of the original free tier (which I imagine we'll have to do eventually).
It's a bit hard to give you advice without a little more information, but here are some ideas:
There are probably dozens of different strategies, and it all depends on what your application actually does and how much you're charging. I really like the model WhatsApp Messenger implemented. You can use the app for free for a year, and then you have to pay $0.99. Users have enough time to test the aplication, and can pay for it if they like it.
If you can, I'd offer a significant discount for upgrading to the paid service for your long term (grandfathered) and thus loyal customers.
I'd also ensure you let them know you appreciate their support in the early stages (e.g. being an early adopter) and thus you'd like to reward them with a nice incentive to the paid service.
Keep in mind that there are many users that will sign up for a free service... but have no intention of every paying for the service (esp. if the free version gives them all they need)
Finally, entice them to upgrade by adding really desirable features in the paid version that the free version does not get.