How to improve upselling and cross-selling with sales enablement



Only 28% of sales leaders say their account managers regularly meet cross-selling and upselling targets.

Even though companies clearly recognize the value of cross-selling and upselling, the reality is that sales teams find this kind of selling difficult, and often need help identifying and pursuing new product opportunities for existing customers.

The good news is that sales enablement tools can help reps improve their cross-selling and upselling. 

In this article, you’ll learn the top strategies for implementing and enhancing upselling and cross-selling efforts, and how sales enablement platforms can help you capitalize on these high-impact sales strategies.


What are cross-selling and upselling?

Cross-selling and upselling are two powerful sales techniques that, when executed effectively, can significantly contribute to your company’s revenue growth. Both strategies involve offering customers additional products or services that complement their initial purchase.

Cross-selling is the practice of recommending related or complementary products or services to customers based on their current purchase or their specific needs. The goal of cross-selling is to increase the value of a sale by encouraging customers to buy more items.

In the B2B world, examples of cross-selling include suggesting an add-on feature or service for a software product or recommending a compatible accessory for a piece of equipment.

Upselling involves encouraging customers to upgrade their current purchase to a higher-tier product or service, typically with added features or benefits. The primary objective of upselling is to increase the overall transaction value by persuading customers to opt for a premium option. In B2B sales, this might involve offering a more advanced software package or a higher level of customer support.

Both cross-selling and upselling are essential for B2B sales organizations because they can lead to:


  • Increased revenue: You can generate additional sales from existing relationships without the need for costly customer acquisition efforts.
  • Improved customer retention: By providing customers with complementary products or services and enhancing their experience, your sales team can foster loyalty and strengthen long-term relationships.
  • Higher customer lifetime value: Through upselling and cross-selling, your company can increase the value of each customer over time.
  • Greater customer satisfaction: By offering tailored solutions and upgrades, your sales team can help customers achieve their goals more effectively, leading to higher satisfaction and more word-of-mouth referrals.
  • Competitive advantage: B2B sales organizations that excel at cross-selling and upselling can differentiate themselves from competitors by providing a consultative sales experience.


Let’s take a look at how your sales team can use sales enablement to facilitate cross-selling and upselling strategies and present relevant, high-value offers to customers.


Essential strategies for cross-selling and upselling success

Cross-selling and upselling can occur at various stages of the customer journey. These opportunities typically arise during the initial sales process, throughout the customer lifecycle as needs evolve, and during post-sales interactions like account reviews, customer support calls, or product renewals.

Wondering how to improve cross-selling and upselling in your sales organization? Put these strategies into action to recommend new or additional products and services for customers.


Leverage data to personalize your cross-selling and upselling

Customers today are demanding personalized experiences with the brands they buy from. In fact, 86% of B2B customers expect companies to be well-informed about their specific needs and preferences during interactions.

By using data-driven personalization, businesses can tailor their upselling and cross-selling efforts to each customer’s unique situation and pain points. Sales enablement platforms can provide the insights and data to facilitate this personalized approach, so your sales team can present relevant and compelling offers to customers.

Here are a few ways you can use sales enablement tools to leverage data and personalize your cross-selling and upselling:


    • Collect and analyze customer data from CRM systems, purchase history, and customer interactions, and use that information to create detailed customer profiles that include their specific struggles, behavior, and preferences.
  • Generate personalized product or service recommendations to ensure cross-selling and upselling offers are relevant and appealing to customers.
  • Customize pricing and promotional offers for each customer.
  • Segment customers based on their behavior, preferences, and other factors, so you can focus upselling and cross-selling efforts on specific customer groups that are more likely to respond positively to targeted offers.

Data-driven selling is on the rise in the B2B world. Sixty percent of B2B sales organizations will transition from intuition- and experience-based selling to a data-driven sales approach by 2025.


Strengthen your cross-selling and upselling with targeted content marketing

Targeted content marketing is a powerful tool in your toolbox for effective cross-selling and upselling. Creating and distributing valuable, relevant, and engaging content that is tailored to the preferences and behavior of a well-defined target audience can help you communicate your value proposition and build trust when presenting offers.

Sales enablement platforms can help you create highly relevant content that showcases the benefits and value of additional products or services that would be a good fit for your customers.

To create and distribute targeted content, you can use a sales enablement platform to:


  • Identify customer needs and preferences, and develop content that addresses those concerns and positions your offerings as solutions.
  • Craft and organize blog posts, case studies, white papers, and webinars that highlight the advantages of additional products and services.
  • Distribute your content to the right audience at the right time.
  • Get valuable analytics — like engagement metrics and conversion rates — to track the performance of each piece of content and refine your strategy for promoting upselling and cross-selling opportunities.

Empower your reps with guided selling

Artificial intelligence (AI) is revolutionizing the way B2B sales teams approach upselling and cross-selling.

Imagine if you could deploy artificial intelligence (AI) to help sales reps choose the most opportune moments to present upselling and cross-selling offers — and even identify the right products and services to present to customers.

Sales enablement platforms with guided selling capabilities can provide real-time recommendations and guidance, helping sales reps personalize their conversations, identify relevant upselling and cross-selling offers, and address customer concerns or objections more effectively.

AI-driven analytics can process vast amounts of customer data to identify patterns, trends, and signals that indicate a customer’s readiness for upselling or cross-selling opportunities. These insights can help sales teams determine the best timing and approach for presenting additional products or services in a natural, non-disruptive way during customer interactions.


Build cross-selling and upselling skills with training and coaching

A well-trained sales team is critical for successfully executing upselling and cross-selling strategies in your organization.

When designing your sales coaching and training programs, make sure you’re equipping reps with the skills, knowledge, and confidence they need to present additional products or services to customers during sales interactions.

With sales enablement, you can help reps master the art of upselling and cross-selling by:


  • Offering a variety of learning resources that are personalized for the individual needs and preferences of each rep.
  • Implementing just-in-time training (JIT) that puts relevant information and resources at reps’ fingertips during the sales process.
  • Giving sales managers the information they need to monitor rep performance, so they can identify areas for improvement and offer personalized feedback on reps’ upselling and cross-selling efforts.
  • Fostering collaboration and knowledge-sharing among team members by establishing a centralized platform for sharing best practices about upselling and cross-selling, including scripts, lessons learned, and sales playbooks

Capitalize on upselling and cross-selling opportunities with sales enablement

Sales enablement can help you optimize your team’s upselling and cross-selling efforts so you can maximize revenue and drive long-term growth for your business. 

Sign up for a demo of Pitcher’s sales enablement platform today and discover how we can help you elevate your upselling and cross-selling initiatives.


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