Knowing When Customers Are Ready for an Upsell Discussion: A CS Professional’s Guide

Never wonder when’s the right time to reach out about upsells with this guide.

Knowing When Customers Are Ready for an Upsell Discussion: A CS Professional’s Guide
Knowing When Customers Are Ready for an Upsell Discussion: A CS Professional’s Guide

Upselling is one of the most significant post-sales revenue generation opportunities by helping your customers get more value from your product while increasing their revenue potential.

But here’s the problem: You can’t just contact every customer to see if they want to upgrade their subscription to the next plan. You have to know when’s the right opportunity to contact them. Each customer will be ready for an upsell conversation at different points in their customer lifecycle. So, how can you tell? We got you covered! Here are the top signs that your customer is ready for an upsell discussion.

But first, What is an Upsell?

Upsell is a popular method that CS (customer success) professionals pitch to their customers about upgrading to a better product, purchasing another one, or getting add-ons.

Top Signs Your Customer is Ready for an Upsell Discussion

Here are the top vital signals that your customer is ready to talk about upselling.

Your customer sees value in your product

Your customers want to see results and get exact value from your product. But that doesn’t mean you should start upselling them the first time they start seeing it. It would help if you waited a few months before this conversation arises, where there’s enough time for them to experience value and want to continue the momentum with a product, add-on, etc., that benefits them more.

Your customers have achieved success with your product

In this stage, your customer is happy, and everything is going well for them. They know the value your product provides and have the results to prove it. If you know there’s a feature or plan that your customer can benefit from that’ll help them scale and increase their ROI, now’s the time to start the conversation. 

Your have access to the decision-makers in the organization

You need to establish trust and maintain a good relationship with your point of contact. This healthy relationship is what will build a business with time.

When you know the best opportunity for upselling, you can escalate a conversation with the decision-makers. Since, ultimately, they’re the ones who have the final say, and they will make a choice based on product performance and results.

You know the customer’s challenge and can map solutions accordingly

Sometimes your customers struggle to reach their desired outcome because the current version of your product might not be what they need. If you know a customer’s challenges, you can propose a product or feature to resolve their issue.  You need to map the product features and solutions to the problems.

They are referring new business to you

If a customer is bringing you new leads and prospects, it means they’re happy. Think of it as a restaurant where a customer asks a friend to visit and check out the food. Only if someone likes the product, they will take the time out to refer it to someone. This is why it’s important to reach out to the customer and thank them for their recommendation. And you can use this opportunity to see how things are going and broach the topic of upselling. Of course, referrals only aren’t a valid reason to upsell to your customers, but if they’re happy with your product and you learn something from your conversation with them, that’ll indicate that they’ll benefit from an add-on or upgrade then mention it.

They’re in the process of renewal

Some professionals might have a difficult time suddenly broaching the topic. But starting a conversation on upselling when you’re already discussing renewal can feel more natural.

Your customer’s company is planning a strategic shift

Your customer’s company might be undergoing a substantial strategic change. This can be introducing a product line or altering their bottom line. Sometimes this shift might mean you’re no longer a good fit for each other. On the other hand, if you see the potential, it’s an incredible opportunity to show them how product upgrades or add-ons can help their business grow in its new direction.16

Bottom Line

Overall, each customer is different. The best time to approach an upsell conversation with one customer might be tone-deaf for another. But with these tips, you’ll know the various times that it’s best to start this conversation with your customer. Customer expansion is one of the primary responsibilities of a CS professional. It’s imperative to show what value can come from expanding since, after all, it is the key driver of growth and customer success.

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