5 Signs Your Customer Is Ready for an Upsell

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Leslie Ye
Leslie Ye



The upsell might be the most underrated play in sales and customer service. A ton of lip service is paid to hunting for new customers -- prospecting, connecting, and qualifying people who have never worked with your company before.


But sometimes it’s hard for sales reps to hunt effectively.Given your company’s lack of history with your prospects, there’s simply no guarantee that prospects will want to speak with you, much less buy your product. Even painstaking research can’t always reveal that what seems like a good fit on paper just won’t cut it in the real world.

But once you’ve built up a customer base, CSMs can start farming -- that is, mining your existing customers for opportunities to upsell or cross-sell.

But you can’t just reach out to every single customer six months after they’ve purchased to see if they want another ride on the merry-go-round. Spotting these opportunities requires the same finesse you use to nurture new customer relationships. Luckily, the five situations below can reliably be used to identify good opportunities for upselling.

5 Signs Your Customer Is Ready for an Upsell

1) They’re seeing success with your product.

The best time to ask for another commitment from your customer is when things are already going well. This situation is particularly helpful when the customer wasn’t ready to commit to a more sophisticated package.

Once they start seeing consistent success with your product, a customer will be more open to restarting a conversation about a more sophisticated package. After all, they’ve started to realize a return on their investment and have seen for themselves that your product works. Think of this initial success as your foot in the door you can leverage to get a bigger deal.

2) Their company is positioned for a strategic shift.

Any time a customer’s company is gearing up for a big change in strategy -- whether it’s introducing a new product line, pivoting on an existing offering, or simply shifting gears -- you should be there.

If you already have a healthy relationship, it’s only natural that a customer will want to go to the next level with a vendor they already know and trust, provided you can sell them something that’ll help in this new endeavor.

3) They’re focused on new priorities.

Most companies don’t face one challenge at a time. They usually have multiple competing projects at any given time that someone needs to prioritize. Which means that once your product is in place and solving an existing challenge, your customer will have time to tackle other items on their list.

Make sure that during your initial discovery you’re doing a thorough qualification. Although your focus should be on the specific product your customer is interested in, suss out your customer's other projects so you have broader context. Then, check in on progress in a few months and see if you can help out with any of the other priorities your customer needs to solve.

4) They’re referring new business to you.

If your customer is proactively sending you new prospects and leads, it’s a sign they’re extremely happy with your product. After all, nobody is going to take time out of their schedule or risk their reputation to send a referral on behalf of a company they’re about to end a relationship with.

In these cases, reach out to your customer to thank them for the referral, then use this as an opportunity to ask them how things are going.

5) They’re growing.

Whether they’re expanding their offices, adding new departments, or simply hiring at a faster clip than they used to, your ears should perk up when you hear about company growth. This means that something’s working (hopefully, something related to your product), and that more cash is now available for your customer to spend.

Growth also indicates that the company is investing in their future and will likely have new needs as they scale. Get in at the ground floor and you’ll be able to feed off the relationship for years to come.

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