skip to Main Content

5 Signs Your Customer Might Be Ready for An Upsell Discussion

Today’s CSMs act as the one-stop go-between for a customer and the rest of a vendor organization. From product announcements to marketing requests, CSMs are typically the point of contact to relay this information to a customer. This same sense of leadership is also true for sales discussions. From renewals to upsells to expansion, the CSM is often the person who either opens up this conversation with a customer, announces to a customer that it is time to start having these sorts of discussions, or loops in a salesperson when the timing is right. So, when exactly is the timing right?

For most CSMs, customer lifecycles are easy to plan but rarely easy to replicate. No two customers will ever be on the same pace in their account life cycle, so there will never be one good moment to bring up an upsell discussion. There are, however, tell-tale signs that are common regardless of your customer profile or industry. If one or more of these signs occur, it’s time to bring in your salespeople to start that upsell discussion.

Here are five telling signs your customer might be ready for an upsell discussion:

1. They’ve seen (and remarked upon) an exact value and/or impact from the solution. 

As a general rule of thumb, customers want to see a clear and tangible value from a solution before investing more time or money in the product. This means that, before an upsell conversation can occur, there needs to be a big ‘W’ in the win column. Whether this is feature-based or results-based, value is critical in jump-starting an upsell conversation.

2. You have access to and can contact the right people – aka the decision-makers – in the customer organization. 

If there is going to be an extensive conversation that involves a commercial discussion, the right people need to be involved. Although you may be dealing with a point-of-contact day-to-day that is perfectly capable, knowing that you have access to decision-makers and can escalate these conversations with them is critical.

3. You have a significant understanding of your customers’ challenges and know exactly how to map your proposed solution(s) to their pain points. 

One of the most important things you’ll encounter in discussions with customers during these upsell conversations is how the newly proposed feature or enhancement will solve their problems. To have this conversation confidently and successfully, you as the CSM should clearly understand the customers’ challenges and how to address these pain points.

4. You are in the middle of a renewal or other conversation where a features-focused upsell would fall into motion organically. 

In most situations, it’s difficult (and unwise) to spring an upsell conversation on a customer out of the blue. It can be awkward and lead to distrust on the customer side. Instead, including upsell discussions in an ongoing commercial conversation, such as a renewal or expansion project, is the perfect time to bring up big-picture solutions.

5. Both the customer and your internal team are aligned on the accounts’ anticipated growth strategy, and the proper expectations are in place on both sides. 

Early on in any customer relationship, both a customer and vendor set expectations on where the account can grow throughout the customer lifecycle. This means that when any commercial discussion comes up (upsells included), both parties understand their roles and know why these conversations are being had.

Want to learn more?

You can explore more resources on having upsell conversations with customers now on ClientSuccess:

Announcing ClientSuccess Goals: Deliver Measurable Results for Your Customers

Back To Top