Customer Success Upsell Strategies and Best Practices

customer success upsell strategies

Each customer relationship has the potential to expand and strengthen. What direction it will take depends heavily on customer success strategies, especially ones related to upselling. 

Upselling is far more than just a sales method, and if you ask customer success managers about it, they will tell you that identifying upsell opportunities is one of the most challenging parts of the job. So, let’s break this through and share with you how to create a customer success upsell strategy that no one will say no to. 

What is Upselling?

Upselling is a strategy that aims to encourage existing customers to purchase a more advanced or premium version of the product they already use. It focuses on boosting the capabilities of the customer’s current solution to bring more value to the customer, as well as more revenue to the company. 

Upselling vs Cross-Selling

Upsell and cross-sell in SaaS can be differentiated within a single sentence – while upselling focuses on motivating customers to purchase enhanced versions of their current solution, while cross-selling aims to expand customers’ product suites by presenting them with additional features or services. Still, both strategies have the same goal – improving customer value and driving growth. 

Adequately identifying upsell opportunities is all about timing. Customer success managers must reach out to customers who are close to renewals, have achieved a certain milestone or have somehow become limited by their current plan. When it comes to cross-selling, it can occur anytime, especially where there is a need that can be adequately met by offering additional services or features. 

By implementing upselling and cross-selling strategies at the best possible moment companies can improve customer satisfaction and build long-term customer relationships.

Before we move on to the new chapter, let us just clear out the confusion around upsell vs expansion. So, expansion is a broader set of strategies that companies use to boost the value gained from a certain customer. Therefore, expansion includes upselling but also cross-selling, increasing usage or adding new teams within the same company to the existing account. 

Who Owns Upsell Opportunities: Customer Success or Sales Teams?

Customer success teams are responsible for maintaining customer relationships by understanding and meeting their unique needs in order to improve customer satisfaction levels and customer retention. On the other hand, sales teams are focused on maximizing revenue through customer acquisition and upselling. They are responsible for negotiating and closing deals, while customer success teams focus on identifying an upsell opportunity that the sales staff can convert into a new financial gain. 

So, when does a customer success team own upsell opportunities and when does the sales team? For example, upselling strategies are implemented solely by customer success teams within organizations that aim to establish deeper relationships with their customers. Sometimes, to understand how to upsell a customer, customer success managers must have in-depth knowledge of the customer’s account and use cases, which isn’t the primary role of a sales team. Over the years, customer-centric culture and approach have gained an advantage over aggressive sales tactics, and more and more companies have adopted them in their business strategies. 

Still, sales teams have expertise in negotiation and closing deals, which can make them more efficient at converting upselling opportunities into revenue. Also, most of the sales teams remain highly motivated by having certain quotas and revenue targets

Upselling should involve a collaboration between customer success and sales teams. This is how the strong points of both departments are used to maximize upsell potential. Like we said, CS teams are responsible for identifying upselling opportunities based on customer feedback, data and interactions, while the sales team aims to convert the potential opportunity into revenue by leveraging their skills and expertise. 

4 Stages of Upselling

Each company has a different approach to how to upsell customers. Oftentimes, upsells are entirely managed by customer success teams, but sometimes, customer success managers are only responsible for identifying upsell opportunities and passing them on to the sales teams. Whichever the approach is, there are four crucial stages of upselling:

  1. Identifying upsell opportunities
    • Identifying these opportunities within the existing customer base is the first step. Key actions include customer segmentation, which is a process of segmenting customers based on their usage patterns and current plans.
    • Using data analytics to identify customers who are close to the limits of their current plan.
    • Getting customer feedback. 
  2. Assessing identified upsell opportunities
    • Assessing identified opportunities is the next step, which includes communication with customers to understand their challenges and needs.
    • Evaluating if the premium or high-tier plan can answer those needs.
    • Checking whether the customer has the budget to consider the upsell. 
  3. Presenting the upsell opportunity to the customer
    • At this point, CS and sales teams have already developed personalized proposals that clearly show the benefits of the given upsell for the customer. It is always effective to present customers with demos that showcase the additional features or premium plans. But, it is most important to create a clear value proposition that includes ROI, improved capabilities, and other benefits. 
  4. Closing the upsell opportunity
    • This is the moment that you’ve been patiently waiting for! At this point, the team addresses any concerns that customers may have before finalizing the upsell deal and preparing the customer for onboarding.

Customer Success Upsell Strategies and Best Practices

Customer success often acts as the backbone of any sustainable SaaS business where customer engagement is deep and retention and satisfaction levels are high. Although the main aim of upselling is to maximize revenue, customers need to feel valued and appreciated at every step of their journey. If you manage to do that, you can expect some great things in return. 

Now, let’s see which are some of the most effective CS upsell strategies and best practices that can help you get more revenue:

  • Listen to your customers
    • Understanding customer needs and goals is vital. Make sure to stay in touch with them, listen to their challenges and needs, and develop a clear understanding of the customer’s journey to be able to recognize the crucial moments for upselling. 
  • Use data and analytics
    • By analyzing product usage data, you can identify patterns that show that a customer may benefit from additional features or premium plans. Also, using health scores as guidelines for customer engagement and satisfaction is highly beneficial, as you can easily identify those who will most likely positively react to the upselling opportunities.
  • Personalized upselling recommendations
    • Customers love when you present them with solutions especially tailored for them. Use customer data to create personalized offerings and include proper value propositions. 
  • Make your offers compelling
    • Offer something the customers can’t deny, like bundles that come with popular features or limited-time offers. 
  • Educate your customers
    • Take time to create training sessions and webinars that demonstrate the value of the given features or services, so that the customers can have a solid preview of the benefits they can get from them. 
  • Build trust
    • Relationship building is one of the most crucial aspects of customer success. Communicate with your customers transparently and build credibility along the way. 
  • Monitor and measure customer success
    • Track KPIs for customer success and improve upselling strategies based on the data and feedback. 

Tips for the Upselling Strategy You Should Know

As a bonus, let us show you a few first-hand tips for upselling that you can use today to maximize the opportunities. 

First, improve your product knowledge so customers get to know your product inside out, also you can better understand whether your customer’s expectations and needs align with what you have to offer. Then, study different buying personas will certainly facilitate the process of understanding how your product fits the current  market needs. Lastly, practice the upsell conversation; this might sound silly, but by smarting small and practicing your “bake” with the current customers, you can go a long way without even feeling discouraged or exhausted!


Having an effective customer success upsell strategy can immensely improve customer retention, satisfaction, and overall business growth and health.

If you manage to understand your customers and their needs to the core, which you can easily do by using customer segmentation software, you’ll be able to provide them with the best possible solutions that they can greatly benefit from, and so will you. 

To conclude, having well-executed upsell strategies, will not only boost your revenue but also help you create long-term mutually beneficial relationships. A pure example of a win-win scenario. 

Frequently Asked Questions

What are the 4 stages of upselling?

Four stages of upselling include identifying, assessing, presenting, and closing the deal.

What is customer upsell?

Customer upsell refers to the practice of motivating existing customers to buy more expensive versions of the products or services they currently use.

What is upsell in customer success?

Upsell in customer success is the process of demonstrating the additional value of features or more expensive offerings within the same product that align with current customer needs and desires.

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