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Upselling and Cross Selling Techniques Service Reps Can Use Today

When it comes to upselling and cross selling techniques, it’s easy to feel intimidated.

Not everyone enjoys selling, and some upselling and cross selling techniques may seem a bit complex to deploy on the spur of the moment.

Still, it’s a good idea to be attentive to these magical opportunities: They represent times when you can add unexpected value for your existing customers.

That’s great for both them and you!

It’s much easier to sell to an existing customer than to find a new one. And, most of the time, you have access to fresh new ways to make customers’ lives easier. The crux of all upselling and cross selling techniques is recognizing when it’s time to draw attention to those offerings.

That means everyone on your team should know your products inside and out.


Armed with that knowledge, you’ll be able to zoom in on opportunities as they arise in the flow of customer interactions. Upselling and cross selling techniques are most effective when they are a natural outgrowth of what’s already happening, not something interruptive.

A little planning goes a long way when it comes to seizing the moment.

Let’s take a close look at six powerful ways to do it.

1. Be Ready to Upsell in Customer Support

Customer support reps, not sales experts, will capture the majority of cross sell and upsell opportunities. With that in mind, they should get ready in advance. Meeting the customer’s immediate need always comes first.

Once you have that solution, build on it with a customized opportunity to try a new product or service that will prevent future issues or make them easier to deal with.

2. Listen Actively to What the Customer is Saying


All selling starts with listening. Offers will only hit the target when they derive from your ability to relate to the customer’s situation.

Identifying and responding to needs often calls on reps to go “off script,” since they may not have a detailed selling plan. When you notice confusion on a customer’s part, consider that they may not yet be using the right product.

3. Strike When the Iron is Hot (Not Before or After)

Not all customer service interactions are selling opportunities.

In fact, there are few things more offensive than “being sold to” in an inappropriate situation. Luckily, you don’t need to consult the stars to figure it all out. There’s a simple baseline to discovering when selling is appropriate.

You should only jump in and sell if:

  • You’re sure the customer is happy with the service you’ve delivered to them.
  • Your customer has an unmet need you can fulfill with a product or service.

Customer happiness is a prerequisite: If they’re not totally satisfied with what they’re looking at right now, they won’t have faith your next offer will do them any favors. They’re more likely to suspect you’re trying to get them onto another subject to avoid dealing with the current problem.

Once a customer is thrilled with where you’ve gotten them so far, then you have the chance to discuss how they can have more speed, more convenience, or more of whatever metric moves their lives forward. The service they’ve received to that moment is what preps the ground.

4. Use Customer Success Milestones as Opportunities

Sales pros check in with their customers when market events change their business situation and create new opportunities for collaboration. Customer service reps don’t usually have the whole picture in front of them, but they can tune in to certain kinds of important changes, too.

Customers go through many noteworthy milestones throughout their relationship with you: These are things like anniversaries, time investment in your app, accomplishing specific tasks (or a certain number of tasks), logging in a certain number of times, or using certain integrations.

These usage patterns give you crucial insights into how your product is already adding value. That provides some clear signposts to the next cross sell or upsell opportunity you should pursue.

5. Maximize Value in Ways Your Customer “Gets”


When you introduce your upsell or cross sell, focus everything on how the customer wins.

Remember, people call customer service to resolve one specific problem. When the conversation starts, they are fixated on that issue – it’s interrupted their busy life. To get them to follow you onto a new branch of the conversation, they need to see what’s in it for them right away.

This is another situation where zeroing in on the critical success factor for your customers is key. You can often start to figure this out by how they describe the support problem they had in the first place. Then, you can center your pitch around improving that aspect of performance.

However, there’s an even better way to get the data you need.

6. Use Your CRM to the Absolute Fullest

Your CRM is the best compass you can have for pointing the way to cross sells and upsells.

With a definitive record of all the brand interactions a customer has had, you can follow the trail of breadcrumbs they’ve been leaving – often without knowing it – to whatever solution will best suit them in the moment. However, you must know the system well enough to navigate it fast.

Your CRM is usually the most elegant way to get information that a customer has previously volunteered, but won’t be eager to discuss in a different context. For example, their purchase history will give hints about their level of price sensitivity you can use to customize a package.

For those who still need a terrific CRM solution, the free HubSpot CRM is our top pick.

The best upselling and cross selling techniques for customer service reps all start from the same place: A genuine interest in how you can make your customers’ lives better.

When you are fully attentive, present, and looking for ways to help, customers are more likely to give you the benefit of the doubt. Then, you can seek out solutions together.

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Rob Steffens

Rob Steffens

I am the Director of Sales & Marketing here at Bluleadz. I'm a recent newlywed who enjoys spending time with my wife vegging out and binging our favorite shows or getting some exercise on the Racquetball court.