3 Upselling best practices every CSM working in a SaaS needs to know

November 24, 2021

Being a customer success manager is not easy, especially in a SaaS. Identifying up-sell opportunities to grow your current client base is something that many new CSMs struggle with. “Learn from the mistakes of others. You can't live long enough to make them yourself”, said Eleanor Roosevelt.

As there are plenty of cross-selling and upselling techniques, it is important to know each technique and avoid certain mistakes to succeed. This guide takes a close look at the best upselling practices to help you take your career to the next level. And do not forget, according to Sumo, upselling increases revenue by 10-30% on average. So do not hesitate to take the step !*

What is upselling?

Before we dive into the top upselling practices, it is important to gain a solid understanding of upselling. It involves encouraging customers to purchase anything additional through the same selling interaction. The sales technique requires companies to invite customers to purchase a higher tier of the service that they are currently using. The main reason why upselling is important is that it allows businesses to increase revenue, generate a higher ROI, boost customer lifetime value, improve customer success, and increase customer loyalty.

There are three phases of upselling as mentioned below :

  • Identifying upselling opportunities.
  • Pursuing those upselling opportunities.
  • Closing the upsell opportunity

What is cross-selling?

A common mistake that new customer success managers make is thinking upselling and cross-selling are the same thing. Cross-selling is a selling technique that involves encouraging customers to purchase an additional product or service that is related to the original purchase to make more revenue. The reason why cross-selling is so important is that it allows businesses to extend their offerings to customers.

Upselling vs cross-selling

Although upselling and cross-selling might seem closely related, the two involve an entirely different approach. Upselling relates to upgrading the same product or service with additional features whereas, cross-selling involves selling different products that are related to, expanding the usage experience of customers. Upselling focuses on the same product at a deeper level, while cross-selling deals with the breadth.

3 Best upsell and cross-sell techniques

Customer success managers need to keep customer interest at the top of their minds. As they get to face customers, it is important to take advantage of their position. The following upsell and cross-sell techniques will help take your business to new heights.

1. Identify the most profitable customers that are worthy of your time

One of the best techniques that CSMs can use is identifying customers that are the most profitable and worthy of your attention. The truth is that not every customer will react in the desired manner when presented with an upsell opportunity. Therefore, you must manage your time wisely by identifying customers you can upsell. This is only possible when you collaborate with other teams and gather all touchpoints. Team effort is necessary for customer success to upsell. Find out when and where your customers could use an upsell by leveraging every interaction that you have with customers.

2. Track usage limit

Another impactful upsell technique that you should consider is tracking the usage limits of customers. You should know the maximum point a customer would reach when using your basic product or service. Approach customers when they hit that limit with more deals. If you notice a drop in usage, you will need to contact the customer and inform them about additional features. Monitor their usage limit and suggest an upgrade once they have exhausted the current limit. You can use an early warning system that will warn you each time a customer is particularly satisfied with your products. Take out time to gain a better understanding of customer success. Keep an eye on how customers use your product.

3. Reach out to customers at the right time

Once you know more about your customers, you also need to make sure that you reach out to them at the right time. Timing is crucial. You can keep track of customer feedback by turning to NPS (Net Promoter Score), support tickets, and QBR (Quarterly Business Reviews).  The higher the NPS of your customers the more likely they are to accept your upsell or cross-sell pitch. Similarly, you should also monitor support tickets to determine if the answer to their problems lies in upselling or cross-selling.

Do not forget to review the quarterly business reviews as they provide the groundwork for understanding what makes your customers happy and if they would be happier with an upsell or cross-sell. Your main goal is to advocate for your customers and ensure that they thrive by leveraging your product or service. Moreover, you also need to keep track of new users and check your customers in the news to learn more about their needs.

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Upsell and cross-sell biggest mistakes

As someone  new to the field, there are certain mistakes that you need to avoid to establish a long-term relationship with customers. Otherwise, you would end up running that relationship and hurting the business. The following upsell and cross-sell mistakes should be avoided at all costs.

1. Considering your customer to be just a number

One of the biggest upsell or cross-sell mistakes that you can make is thinking that your customers are just a number. Instead, your goal should be to build a strong relationship with them. You need to find ways to retain your customers rather than just trying to upsell or cross-sell to them. Never approach your customers without a plan.

2. Waiting for the right time

There is always the right time for something. You must get your timing right as it is a critical factor that influences upselling and cross-selling success. After preparing a list of customers to pursue, you must ensure that your customer is on the right track of the customer journey before reaching out to them. Consider the major customer journey, from onboarding to renewal. The last thing you want is to overwhelm your customer during the onboarding phase with advanced features. Hence, you must think about timing.  

3. Not staying updated about your customers

Lastly, you cannot just assume that your customers would remain the same. Therefore, you must stay updated with the current scenario. It will allow you to adjust your offerings accordingly. Continuously analyze how their needs have evolved by reviewing discussions and finding ways to incorporate those changes to succeed.

To sum up, you should keep an eye on your potential client and build a strategy before meeting them. You should know how, when, and with what you have to approach them to be the best and succeed. Do not waste your time and focus on businesses that you can help and that can help you back to grow.

* Bill Widmer, April 25 2019, “Ecommerce Upselling: A Step-By-Step Guide To Increasing Sales”, Sumo,

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