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5 Vital Signs Your Customer is Ready for An Upsell Discussion

Upsell discussion happens when your product either delivers expected value or exceeds it. So obviously the focus of salespeople and the Customer Success Managers (CSMs) should be to help the customers achieve their desired outcomes. This blog attempts to list 5 crucial signs that indicate that your customer is ready for an upsell discussion.

Wait, what’s an Upsell? 

An upsell is a technique used by, usually, the salespeople and/or CSMs to pitch to the customer to consider either purchasing an expensive product or upgrading to a more feature enhanced product. CSMs are usually the point of contact to provide information to the customer. They play a crucial role in customer-facing teams and mostly, have a multitude of responsibilities to be carried out. From renewals to expansion, they initiate the conversation with the customer at every possible opportunity. They also rope in the sales team at the right time for specific discussions.

Suggested Read: How to build an upsell strategy for your b2b SaaS product?

Upsell opportunity Template

CSMs understand that no two customers are the same. Customers from similar industries, with similar profiles, may have distinct customer journeys with a product. Though these are easy to plan but difficult to execute. Hence, there’s no one similar  ‘moment’ where you can just go and have an ‘upsell’ discussion. 

There are, however, some visible signs that are common irrespective of your customer profile. You need to be alert and jump into action if you come across any one of these tell-tale signs. Inform your team and the customer announcing the right time to start the upsell discussion. 

5 Vital signs your customer is ready for an upsell discussion

Here are the 5 important signs that signal your customer is ready to have an upsell discussion.

5 Vital signs that your customer is ready for an Upsell Discussion

Customers achieved success using your product. 

This is the best place to be in. Everything is going well for the customer and they’ve realized the value your product has to offer. As a general rule of thumb, customers would want to realize a clear value before investing more money in the product. They see for themselves that your product works and solves an existing problem. This means that they see the tangible value in your offering. 

Once that happens, a customer will be open to initiating a renewal conversation. It depends upon the other attributes if the conversation can be tilted towards ‘Upsell discussion’ or not. 

Suggested Read: Strategies to Increase Upsell opportunities

You have a good understanding of customers’ business challenges.

In these Upsell conversations, one of the most frequently asked questions by customers is how the newly proposed feature will solve their business problems. As a CSM you need to know your customer’s business in and out to have this conversation confidently. 

The problem is that most firms don’t face only one challenge at a time. They usually have multiple projects at a given time. These competing projects need to be prioritized according to the complexity of the issue they’re trying to solve. This means that if your product solves an existing challenge, your customer will have time to tackle the others. Eventually, it will be just a matter of time before the customer opens up for the upsell conversation. 

Drive Customer Success throughout the Customer Journey!

You maintain good relationships with decision-makers.

It’s natural for a customer to go to the next level with a vendor they trust. It doesn’t happen overnight. You’d have to build trust by providing a solution that the customer needs. Maintaining a good relationship with your point of contact is important. Yet, having a healthy relationship and access to the real decision-makers changes the game. 

If you identify a great opportunity to start an upsell discussion, then having the same with decision-makers can escalate the conversation. These are not the people who’ll upgrade your product because you said so. They make decisions based on performance and results. If your customer realizes the value by using your product, then having a healthy relationship with key people will ease your job of having the upsell discussion.  

Upselling doesn’t happen overnight

Renewal Conversation is already happening. 

Most of the time it’s unwise and difficult to have an upsell conversation with the customer out of the blue. It can lead to distrust on the customer side and can be awkward at your end. Rather than surprising the customer, spring up the relevant conversation when you and the customer are already discussing the renewal plan. This is the best time to set the ball rolling with a feature-focused upsell discussion. Bringing up these discussions in an ongoing commercial conversation is the perfect way to conduct them. Check out these upsell strategies that can improve your bottom line!

Customers are growing.

Keep an eye out for changes in your customer’s business landscape. Whether they’re hiring, adding new functional departments, or expanding their offices, it is a signal of possible company growth. It also possibly means that your product is working. You just need to identify the right time and opportunity to present the case for the discussion on expansion. The company growth is one of the vital signs that your customer is ready for an upsell discussion. 

Growth also indicates that the firm might have enough cash to invest in crucial needs as it scales further. Pitching for the up-gradation by focusing purely on the feature-specific value at the right time will set the right environment for upselling discussion. 

Pro tip:  Check out the Upsell Opportunity Template here. 

Final thoughts on Upselling

Acquiring a new customer is much costlier than keeping an existing one. So if you want to generate more revenue from an existing customer, they need to realize the value that your product offers. Once they do, you need to start mining them for potential upsell and cross-sell opportunities. But, you can’t just go out and ask every single customer of yours to upgrade or renew. You need to spot the opportunity where you can confidently pitch about the upsell. That requires finesse. 

However, be aware of the 5 mistakes not to make while trying to increase upsells. Avoid them and keep an eye out for any of the 5 vital signs. Presenting your case at the right time will surely convert into upsells. 

P.S. – The main image has been taken from

Content marketer at CustomerSuccessBox | An avid reader, a passionate writer and a life long learner | Writer @ Hacker Noon | B2B SaaS & Customer Success enthusiast |