We've all experienced it – you're wrapping up an online purchase when complementary product suggestions appear: "Customers also bought... X" or "You may also like… Y or Z." 

This is cross-selling, a strategy that encourages customers to purchase additional, related products or services alongside their initial purchase. For customer success professionals, cross-selling isn’t just a revenue-driven initiative; it can be a powerful tool to drive loyalty, increase customer lifetime value, and ultimately enrich the overall customer experience.

In this article, you’ll learn:

  • What cross-selling and upselling are
  • Some examples you may have come across
  • The best practices for you to consider

The fundamentals of cross-selling 

At its core, cross-selling aims to boost revenue by enticing customers to expand their purchasing beyond their initial intent by recommending relevant add-ons, complementary offerings, or supplementary services. 

It differs slightly from upselling, which encourages upgrading to a premium or higher-tier version of a product or service. While both strategies seek to increase sales, cross-selling focuses specifically on complementary products or services rather than upgrades.

Cross-selling hinges on understanding your customers' needs, pain points, and usage patterns and then presenting tailored recommendations that genuinely add value to their experience with your products or services. It's about enhancing their overall journey and fostering a deeper, more valuable relationship.

10 upselling best practices every CSM needs to know
When I first started as a Customer Success Manager (CSM), one of the most challenging parts was identifying up-sell opportunities to grow current clients. There’s no doubt that there are so many different upselling techniques.
Customer Success CollectiveGözde Görce

Mastering the timing 

Timing is pivotal when it comes to effective cross-selling. Bombarding customers with product pitches when they're dealing with support issues, expressing dissatisfaction, or experiencing challenges is a surefire way to agitate rather than engage. Instead, you'll want to identify and capitalize on opportune moments when the customer is already in a positive purchasing mindset or when their current needs and behaviors indicate an organic opportunity for a complementary offering.

The point of purchase is often an ideal time for cross-selling, as the customer is already engaged in the buying process and may be open to considering additional solutions. In-app triggers, personalized in-product messaging, or tailored communications based on observed usage patterns can also reveal well-timed cross-sell opportunities organically. 

Another savvy way to introduce another product is after they’ve hit a key milestone. Perhaps they’ve spent 1000+ hours (approx. 250 days if they’re using your product four hours per day), the next best step would be to showcase other products you offer related to their current product.

Customer success and cross-departmental collaboration
We all know that effective collaboration is the key to success in any organization. However, sometimes collaborating across departments is easier said than done.
Customer Success CollectiveJoseph Latteri

Collaboration is critical 

Effective cross-selling requires close collaboration and coordination between multiple teams within an organization, including customer success, product marketing, customer marketing, sales, and potentially data or analytics teams. Each department brings unique expertise and perspectives to the table.

Product marketing teams can harness data and customer insights to identify distinct customer segments based on behaviors, preferences, and usage patterns. This segmentation can inform tailored cross-sell strategies for different customer groups.

You can work closely with your customer marketing team to craft compelling narratives, messaging, and content highlighting the value propositions and use cases for cross-sell offerings, making them resonate with specific customer needs.

Who drives cross-selling initiatives entirely depends on who owns the responsibility for account expansion in your organization; for some companies, it’s a wholeheartedly sales-led venture. For others, it’s a customer-success-led initiative. In a lot of B2B organizations, sales may drive cross-sell efforts through direct customer interactions, equipped with a deep understanding of the customer's business and objectives.

But it’s you, the customer success professionals, who perhaps play the most crucial role of all. With your intimate knowledge of individual customers' unique needs, challenges, and journeys, you're perfectly positioned to identify highly relevant cross-sell opportunities and make tailored recommendations that genuinely enhance the customer's experience.

Making cross-functional collaboration the linchpin of your cross-sell strategy, you also establish the significance of your customer journey map. By focusing on your customer journey map, you’ll find it easier to identify the optimal time(s) for a given segment. 

For example, if onboarding data looks good and engagement is steady, it might be a good time to follow up with upgrade nudges. Automation can come into play, depending on your organization’s capabilities - AI tools can automatically contact customers who display interest in certain products.

Best practices for effective cross-selling 

When approaching cross-selling as a customer success strategy, there are several key best practices to consider:

1. Let customers experience value with freemium models

One of the most powerful tactics is to provide customers with a taste of your premium or expanded offerings through free trials, limited-time feature previews, or temporary access to upgraded capabilities. This allows them to organically experience the added value, convenience, or enhanced functionality, naturally cultivating interest and desire for the full-fledged solution.

2. Personalize, personalize, personalize 

Generic, one-size-fits-all cross-sell recommendations are unlikely to resonate. Ask yourself, how many times have you been overtly sold a product that has very little in common with your own interests? It’s jarring, boring, and just plain sloppy! 

Using the wealth of customer data and behavioral insights you have at your disposal, tailor your cross-sell offerings to directly address each customer's specific needs, use cases, and pain points. Personalized recommendations demonstrate a deeper understanding of the customer's unique situation, making the value proposition far more compelling.

3. Position cross-sells as solutions, not sales pitches 

Rather than pushing products or services for the sake of making a sale (we’ll repeat: boring!), position your cross-sell offerings as tailored solutions to the customer's expressed challenges or unfulfilled needs. 

Listen *intently* to the issues or gaps they're experiencing, and present your complementary products or services as the means to alleviate those pain points or take their experience to the next level. This consultative, solution-oriented approach builds trust and reinforces your commitment to their success.

4. Use multiple channels and touchpoints 

While in-app prompts, customer success interactions, and sales conversations offer prime cross-sell opportunities, don't overlook other channels in your arsenal. 

Email marketing, newsletters, educational content – and even social media – can serve as powerful vehicles to highlight cross-sell offerings in contextually relevant ways. A multi-channel approach reinforces the value proposition and keeps your solutions top-of-mind.

5. Continuously experiment, measure, and optimize 

Cross-selling is an iterative process; there’s no doubt about it. In order to successfully cross-sell, you must follow these three simple steps:

  1. Continuously gather feedback
  2. Analyze customer behaviors and responses
  3. Closely monitor the performance metrics of your cross-sell initiatives

We encourage you to test different messaging approaches, timing, delivery channels, and offers – if you’re new to cross-selling, a lot of it will come down to trial and error. 

Don’t be afraid to experiment and find what works for your products and specific audiences. You can then use these insights to refine your strategies continuously, optimizing for maximum effectiveness and resonance with your customer base.

The power of cross-selling for customer success 

At its core, cross-selling aligns seamlessly with the fundamental goals of customer success - driving sustained value, forging deeper relationships, and cultivating long-term loyalty. By thoughtfully recommending complementary solutions that genuinely enhance the customer's experience and address their evolving needs, you solidify your role as a trusted partner invested in their success.

Embrace cross-selling not as a sales tactic but as a customer-centric practice that enriches the overall customer journey. With strategic collaboration across functions, data-driven personalization, and a solutions-oriented mindset, you can transform cross-selling into a powerful driver of customer satisfaction, retention, and growth.

As a customer success professional, you hold the key to unlocking successful cross-selling strategies. Your unparalleled customer insights, combined with a relentless focus on delivering exceptional experiences, position you to tailor cross-sell offerings that resonate, add value, and foster enduring, mutually beneficial relationships with your customers.