How do you enable sales reps to sell higher priced packages vs your lower priced offerings?

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 

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.

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.

Driving upsell is all about real value.

1. Be real about your positioning, and test the underlying hypothesis for your up-sell play. Is there value? Are the features locked in enterprise editions meaningful? do they unlock speed/revenue/margin for the customer? If all of these are true, great! Its a problem of articulating and communicating that value. If not, you have some tough conversations with your product and sales teams to identify where you are falling short of customer expectations.

2. Have you made it feel real for buyers with case studies and references? Do you feature a spread of customers across industries and sizes? geography? and do those assets speak to real business outcomes?

3. For PLG, is it real outside of a sales motion? Do you have in-depth demos and product walk-throughs available online? ROI Calculators? Whitepapers and playbooks for adoption?

4. Is the value real for the economic buyer and procurement team in an enterprise? Are reps supported to influence at the most senior levels of leadership? Are executive-level presentations, and executive leaders from your company available to help get the deal over the line? (Think about your Product leadership who can inspire confidence in the roadmap, your Engineering leadership to inspire confidence in your security, data handling and reliability, and your CEO can help drive a peer-to-peer partnership for the long-term).

By arming your teams with these resources, you'll empower them to effectively communicate the value proposition of your high-priced enterprise packages and differentiate them from lower-cost alternatives.

If your product tiers are naturally cannibalizing each other, then you likely have a product strategy problem , or a pricing & packaging problem. The product strategy should build more differentiation for your enterprise plan, and a good packaging/entitlement structure, or pricing barriers, should create differentiation paths

But if you truly don't have those levers at your disposal, I would focus on helping your sales teams understand the difference between the three tiers less in terms of the features within them, but more in terms of the value they represent

e.g. Some cases, Lower tier is for individuals, Middle tier is for Teams, Highest tiers for entire functions / multiple organizations. Focus on capabilities and their benefits that stress upon this difference

In some cases, highest tier packages contain the kind of security/compliance/governance/privacy/role based access/user management controls that only become meaningful for large enterprises/above a certain scale. Focus on those differences, than individual features

For enablement, bring this to life not just via messaging statements but also via customer stories