Sales Skills to Help Your Team Effectively Cross-Sell and Upsell

Sales Skills to Help Your Team Effectively Cross-Sell and Upsell

Categories: Sales Messaging  |  Sales Process

In today's economic climate, cross-selling and upselling have become more challenging due to the budget constraints of customers. While gaining new customers is always a positive outcome for any organization, the ability of your sales representatives to sell additional products or services to existing customers is often the key to meeting your revenue targets consistently.

Unfortunately, many sales leaders may instruct their teams to pull resources from existing accounts in an effort to meet quarterly goals, without equipping them with the necessary tools and strategies to succeed in upselling. This can lead to disorganized sales behavior and increased discounts, creating unnecessary stress for managers and sales representatives alike as they try to close deals that are not yet fully developed.

To effectively cross-sell and up-sell, your reps need to master the fundamental sales skills. Cross-selling and upselling should be part of their regular operating rhythm. Here are three key sales skills to help your team cross-sell and upsell.

1. Digging Deep in Discovery

You can’t effectively cross-sell and up-sell if your reps can’t uncover the pain points and their business impact. Many sales teams use role plays to provide reps practice in having the sales conversation. Role plays can also be effective in training reps to use silence and effective questioning to truly uncover the business impact.

Effective discovery requires the right question flow (here are some podcasts on that topic) as well as an ability to feel comfortable digging deep on negative consequences. Salespeople are natural problem solvers. They want to solve problems, not talk about them. However, if your salespeople are unable to dig deep into the problem they won’t be able to effectively quantify the pain that demands a premium price. Here are some actions you can take as a sales leader to support your sellers in expanding accounts:

  • Create opportunities for your reps to practice effective discovery with role plays. Observe them on phone calls and listen specifically to their discovery skills.
  • Identify the reps whom you think do a great job of uncovering business pain and provide opportunities for other reps who need coaching to observe them.
  • Encourage your sales representatives to structure their questions around the end goal and become comfortable with silence, avoiding the panic that leads to preemptive discounting.

2. Clarity on How You Create Value for Customers

When it comes to providing for your sales representatives, nothing beats a framework that enables them to demonstrate how they can add value for their customers. To ensure your reps are well-equipped, make sure they have a clear understanding of the following: 

  • Who are the target buyers for the problem your product is solving? 
  • What are the key value drivers that compel these buyers to take action? 

You may think you have a clear idea of the answers to these questions, but do all your reps share the same clarity? Are your digital marketing materials conveying the same value? And is your product/service team ready to deliver that value?

To address these issues, start by assessing your organization's value proposition using the above questions. Then train your reps on the value drivers and how to deliver them. Without this understanding, your reps won't be able to expand your customer base or sell more to existing customers.

Remember, building clarity is an ongoing process that requires a shift in mindset—from inside-out to outside-in. This requires a transformation in many organizations, so treat it as a continuous process rather than a one-time shift. With this approach, you'll be more successful in implementing meaningful change in your organization.

3. Articulate Differentiators in a Way that Has Meaning to the Buyer

Many salespeople tend to list off different product or solution features that set them apart from their competitors. However, the challenge is that these features and functions often hold no real significance for the economic buyer. For instance, why would a buyer care that a product offers unlimited licenses if they only have a team of 10 members? (although it might matter if they plan to expand their solution to their sales team to improve data insights between marketing content and revenue generation). 

When cross-selling and up-selling, it's important for salespeople to be able to align the differentiation with what is meaningful to their targets. Your reps should understand the following three points: 

  1. If they're expanding their solution, what is the business problem they're aligning with (related to the value drivers mentioned above)? 
  2. What is important to the decision-maker in relation to the solution requirements? 
  3. How do your differentiators align with those requirements? 

Teach your reps to navigate cross-sell and up-sell conversations effectively by mapping out these three components. A pre-call or pre-meeting planner can be a useful tool to ensure that their conversations are focused on uncovering these critical components as they relate to differentiation.

The Skills To Support Your Revenue Goals

In today's evolving economic climate, equipping sales teams with the necessary skills to cross-sell and up-sell is crucial. The ability to sell to existing customers is the key to meeting revenue targets consistently. Download our newest leadership guide, Command What's Next: A Guide to Sales Evolution, for more strategies to ensure your team is ready to support your revenue goals in a transitioning economy.

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