Pricing should disappear. After customer asks for your pricing, you give it to them, they should think "that seems fair" and then the customer should never have to think the pricing again.

The only thing certain about pricing is change. You need to keep iterating it constantly. When you improve your product, it provides more value and users are willing to pay more for it.

Use pricing scheme that scales with usage. This is the best way to compensate for users leaving your product while others increase their usage.

the number of seats used
the number of leads tracked

Use pricing scheme that allows cross- and upselling. Also helps to combat users leaving while other get more advanced in their usage. Don't offer all features at once, only the most important ones.

more powerful versions of your product
sell more features as modules

Consider cutting your lowest price point. $9/month customer often costs just as much to acquire and support as $499/month tier customer. And it's less frequent that the small customers grow to higher tier.

Sources

• The Growth Handbook, Intercom