Our lower priced offerings seem to be the biggest competitors of our enterprise packages. What sales enablement activities and content help your sales reps sell your high priced packages?

Your room to maneuver depends on whether you have a fully transparent pricing model reflected on your website or if it is somewhat general on the pricing page so that your reps can customize. 

If I were to guess, this is a transparent pricing page on your website.

1. Package Definition: It could be worth considering what would increase package differentiation more so that your prospects have a clear choice in front of them. To do this correctly it is important to try to reduce the overlap between the segments targeted by the packages. You can also consider adding a decoy package to move people to a clear choice. See famous example from The Economist

2. Sales Process: If you are not a company with completely transparent package prices on your pricing page, then you can actually offer the right package to the prospect vs getting into the shop-a-package discussion. You really want to avoid the latter discussion if cannibalization is a risk. Do this buy ensuring there are no comparitive package collateral or slides available to your reps and train them not to compare packages. Give them total control of the sale. The packages exist to capture the maximum value from the market and this already aligns with your sales reps' incentives, use that to your advantage. 

It sounds like you may be cannibalizing yourself with overlapping product offerings. If customers are happy to use your cheaper product, it means the value of your enterprise package isn't crystal clear. I'd go back to the value prop on this one, what does your enterprise package offer the customer that's worth the price? If you feel you have that figured out, then it's just a matter of illustrating that through messaging. Show some super specific examples of enterprise brands that have seen killer value from upgrading and you'll have a more convincing narrative.

Another option here is to not give Enterprise customers the option of having a lower priced package. Depending on your pricing model, you can usually justify charging larger customers more because they use more data/have more servicing needs/etc.

Value selling is a really tool you can have in your arsenal. I would do a few things here if you're focused on having them shift to higher selling things.

(1) Articulate Value - what is the customer getting for paying more? What are the benefits they would gain with this?  

(2) Teach them to place competitive traps - what are questions they could be asking their prospects to place some FUD in their minds? I have done things like "below the iceberg" documents for AEs which teach them all the things that the customer may not be thinking about in terms of all the below the surface stuff that technology needs to have in place that a more expensive solution could be (e.g. security, performance, etc.). 

(3) Make sure they have the tough questions down and know how to answer it like the back of their hands

(4) Customer stories, testimonials, and references from customers who bought the more expensive products and felt it was worth it 

This is a typical issue when you have both a self-serve item and an enterprise item. The most important thing is to have clear differentiation in your packaging and then clearly articulate that differentiation for the sales team so that they understand how to pitch the value of your enterprise package.

It is also really important that you have a very clear GTM strategy for Enterprise with a very distinct ICP - you should not be targeting the same audience for both packages, to begin with.