Cross-selling can be a cringe-worthy concept for customer success teams to tackle.

With a focus on assisting customers and avoiding dollar discussions, the idea of selling can seem counterintuitive to the role of a customer success manager (CSM) or anyone else in a customer support role.

But consumers' purchasing decisions are greatly impacted by personalization factors. If they're recognized, offered relevant recommendations, or remembered by businesses, they're 75% more likely to buy a company's products again.

CSMs are a part of a customer's entire journey -- especially during critical moments like onboarding, renewal decisions, and resolving problems with the product. If value and trust are established with the customer, it can lay a powerful foundation for growth and long-term customer retention. And since personalization and relationships with a brand are so important to consumers' buying patterns, CSMs can -- and should -- be an essential part of revenue generation by cross-selling. 

How should customer success teams approach cross-selling without losing a customer's trust? And what are some cross-selling best practices for CSMs? Read on to learn more about cross-selling, as well as strategies and cross-selling examples to add to your customer success playbook.

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What Is Cross-Selling?

Cross-selling to a customer is different from upselling to a customer. Cross-selling is intended to contribute to an original purchase made by a customer with a complementary product.

"Do you want a scoop of ice cream with your piece of pie?"

Many waiters use cross-selling to add additional value to your meal -- and to increase the bill in hopes of earning a bigger tip. If the piece of pie is the original purchase, ice cream would be the complementary add-on product. This difficult decision at the end of a meal is just one of many encounters you probably experience with cross-selling every day.

How to Do Cross-Selling

For many customer success teams, talking about a customer's budget can be an uncomfortable conversation. In order to prevent your customers from dodging your calls and emails, let's walk through the right questions and precautionary steps to bridge the gap between selling and helping the customer.

  1. Research and ask the right questions to become the customer's trusted advisor.
  2. Find the customer's barriers to success.
  3. Structure your cross-selling pitch.

Gaining "trusted advisor status" as a CSM is essential to understanding the customer -- and it's the first step to building a good relationship. Before speaking with them for the first time, look at their website, read an article about their industry, or find them on LinkedIn. Coming to the first meeting with previous knowledge demonstrates preparation and a commitment to helping them.

During the first interaction -- via email, web meeting, or in-person -- ask the right questions to ensure you fully understand your customer's business and goals. "What is your business goal for this quarter? How can I help you achieve these goals? Why did you decide to purchase this product?"

By understanding these key foundation pieces, customers will lean into your recommendations, best practices, and general advice. If customers can derive immediate value from the original purchase, it will be easier to encourage them to invest more in the future -- and that's where you come in with your recommendations and guidance.

When problems arise, ask your customers the tough questions. "Do you need to generate more leads to pass along to your sales team? What tools are essential to improve retention this quarter? How are you keeping track of the employees you are recruiting?"

By bringing to light underlying problems, you help customers bring their guard down and think about what problems they need to solve -- which allows you, the CSM, to suggest other products and services that might help them more effectively. If the customer is already having a pleasant experience, they'll trust you to make the right recommendations for them.

Highly engaged customers buy 90% more frequently and will purchase up to 60% more per transaction -- and emotionally engaged customers will buy more of your products and be less sensitive to price and service changes. If you can find obstacles to the customer's progress, it'll make them sit up and pay attention to you -- increasing their engagement and leave them reaching for their wallet to alleviate problems.

Let's be real -- there's nothing worse than receiving an unsolicited phone call or email from an unexpected stranger asking for your money. Leaving the customer with a bad taste in their mouth if you pass them off to a sales rep too quickly for a cross-sell opportunity -- or continue to ask them to purchase another product if they've already declined -- is not good practice.

Avoid these mistakes by blending the role of trustworthy CSM with an aggressive sales rep in your conversations. First, state the initial intent for what you're trying to accomplish, then clearly explain solutions to the customer's barrier to success, and finally, ask customers if they're open to a conversation about buying more products or services.

Stating the initial intent allows CSMs to explain that their primary goal is to help them -- and that by suggesting other products, CSMs are looking to solve for the customer's business. Asking permission to move a conversation towards cross-selling is critical to putting the customer in the driver's seat, allowing them to steer the conversation.

"As your Customer Success Manager, my job is to help you with the product you purchased. With that being said, it seems that in order to attract more leads, our marketing product would help you communicate with triple the number of people you are meeting at trade shows. Are you open to learning more about our email campaign product?"

If you receive confirmation that a customer is interested in a product, ask them if they would be interested in reading more information about an additional product, starting a free trial, or learning about prices and packages.

By following these three steps for a seamless dialogue, you'll allow the customer to make decisions for themselves -- according to your expert recommendations.

Some Good (and Not-So-Good) Examples of Cross-Selling

Let's take a look at some examples of CSM cross-selling scenarios and outline the difference between a poorly executed cross-selling attempt and an effective cross-selling strategy.

Bad Customer Success Cross-Selling:

The customer buys an email campaign tool for $50 per month. After speaking with them, you find out that they work at a startup with three employees pinching pennies wherever they can. Right now, their focus is on converting more of their existing leads into customers. Despite this knowledge, you suggest they purchase the full suite of social media products for $1,000 per month, and quickly pass their contact information over to the sales rep for them to close the cross-sell.

To be successful at cross-selling, the key is the understand what the customer needs, and what they can afford. In this example, the customer needed to derive maximum value from the more affordable product -- before being offered a more expensive add-on.

Effective Customer Success Cross-Selling:

The customer purchases email tracking software that costs $10. As the CSM, you ask them discovery questions-- (What is your job responsibilities? Name one area in your sales funnel that you can improve upon?) -- the answers to which reveal that the customer is a sales rep at a mid-market consulting company looking to bring in more leads and keep track of their pre-existing contacts. You expose their barrier to success when you find out that their contacts are stored in their email inbox -- with little to no organization.

With these details in mind, you first state your initial intent -- to assist with the email tracking product they'd purchased -- and then ask if they would like to learn more about your company's CRM. The customer expresses interest but asks how much it would be. You inform them that it costs $50 a month and encourage them to sign up for a free trial -- and assure them that you'll walk them through the setup process.

Effective cross-selling starts with conducting discovery to achieve trusted advisor status, identifying barriers to success, and structuring a conversation with appropriate next steps. The CSM should be able to identify if a customer is a good fit for the product they already have before suggesting a new one -- especially if requires a price jump. Ending the conversation by continuing to offer help to a customer makes a new purchase less daunting and establishes more trust and consistency.

What are your strategies and best practices for cross-selling as a CSM? Share your thoughts with me on Twitter.

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Originally published Feb 2, 2018 8:00:00 AM, updated May 08 2020