Pricing is the easiest & most neglected way to make more money.
How to raise prices without making everyone hate you...
Talk up the value you are adding. No one wants to pay more, but customers feel better if they are getting more value with it.
The price increase is necessary to maintain product quality, add new features, increase in costs, etc.
Push the date off
Give customers a warning well in advance.
The ones that want to leave can do so. The vast majority that remain will appreciate the warning and be less concerned because it is off in the future.
Don't be sneaky. Let customers know exactly what is happening before it happens.
This price increase is happening on this date...
Wavering will hurt your credibility.
Stay strong and don't make exceptions. If the price increase is necessary then there shouldn't be wiggle room.
People will complain. Just explain yourself again.
Many that threaten to churn never will. The few that churn are worth the increased revenue.
Make it a habit
Big jumps are painful. It is better to get in the habit of raising prices in small amounts annually.