What is the best approach for rolling out pricing and packaging changes? Especially increases in pricing or restrictions to features without angering customers?

With limited context into your exact situation, I can share some initiatives/tactics I have employed in the past to execute price increases or restrictions to features:

1. Understand your customer base, assess the impact of pricing or feature changes for different customer audiences, and build communications based on those insights. There may be some customers that recommended changes may disproportionately impact, so preparing tailored communications by key audiences can help soften the pricing news across your base and help address critical questions your customers may have. For example, in a past role, our team decided to delay pricing changes by six months for a select group of customers who a separate pricing change had recently impacted.
2. Be ready to justify pricing changes beyond macroeconomic or cost of doing business rationale. Ensure your announcement and related messaging anchor on the value your product offers to your customers vs. just informing them of the changes. Educate your internal stakeholders on the "why" behind the pricing/packaging changes (e.g., research conducted, options explored during pricing discussions, and the reasons for pricing) and the "how" to explain differences to customers.
3. Be transparent about your intentions as you release features by crafting messaging that communicates the incremental value that each feature or capability delivers to your customers. Many companies build features over multiple quarters to justify future-state pricing, so it is essential to communicate your vision to customers and build trust with

Let's just agree that no likes paying more for the same thing and no one likes having things taken from them. So your job is 1) to not let them see it that way, 2) decide a method for grandfathering customers in and/or 3) be willing to take a bit of PR hit. Regardless of what you choose, you need to give customers time to adjust - the larger the change, the more time they need.

For #1 -- Ideally you can do this after a major launch / release which introduces new uses cases to your product. That helps align the view that new value = new $$. Of course, that's often not possible. The best way I have found is to be honest with your customers. If you're committed to building the best product, best service and best experience for your customers, it's going to cost money. So tell them about your vision, tell them about what you're building next and tell them that the new pricing is to make sure you can continue meet their needs better than any other product out there. Keep it short, keep it simple and don't try to oversell it. Customers aren't going to be psyched about it, but they can be understanding if you are straightforward with them.

For #2 -- Grandfathering customers into old pricing can be a slippery slope - so ideally this is a last resort. The problem with grandfathering, aside for the lack of revenue growth for certain customers, is the overhead of managing a group of customers on a non-standard plan. When you choose to grandfather customers, the best way to do it is to lock in their feature-set and block them from future improvements. Basically say - we're going to let you stay at your current rate, but you won't benefit from any new developments we make. This is another reason why timing a pricing increase after a launch can work well - most people want to have the latest and greatest.

For #3 -- this is going to be a judgement call. Sometimes grandfathering in just doesn't make sense. Either it's too complex to manage or too costly. In these cases you need to do scenario planning to understand the types of customers who are likely to be upset and come up with a communication strategy for them. Acknowledge their frustration, lay out options for them, but ultimately make it clear that the status quo is changing. For these customers, you have to accept that they will likely leave your product if they can find an alternative - so make you have know how big of a hit this might be.

Across all of these - make sure you have a well thought through communication plan for everyone in your company to follow. One wrong statement by someone in your organization can undermine the whole transition - so make sure everyone is aligned and equipped with the right talk tracks.