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How to Upsell Your Customers The Right Way ( +10 Examples)

All in all, there are two major approaches to driving more sales revenue: Getting new accounts or growing the value of existing ones.

If your enterprise has a strong inbound marketing operation, you probably already have your pipeline full of eager, highly qualified new leads. But, no matter how well things are going in terms of new business, existing customers still represent a huge reservoir of opportunity.

Upselling is one way to take those relationships further.

What Is Upselling?


If your enterprise provides solutions with many tiers of service, then upselling is probably for you.

Upselling is expanding value by getting customers to move to a high-end product, usually a version of one that they already use. Sales pros have a great example of this in their back pocket: Customer relationship management (CRM) systems and other productivity software they rely on daily.

CRMs are usually licensed to sales teams based on either the number of distinct users (“seats”) or the number of contacts they need to keep track of.

Email marketing software works the same way; so do many other tools used in SEO, web development, and digital advertising.

In effect, upselling makes an existing, primary product more expensive.

The question is: How do you know when it’s the right time to upsell?

Customers tend to be ready for a “new and improved” solution when they reach a bottleneck with their existing one. What this looks like from your perspective depends on the nature of your offerings. In software, there are some telltale signs:

  • Multiple users keep using one account instead of creating additional ones that cost more.
  • The customer frequently reaches any monthly resource limit before the end of the month.
  • Customers consistently try to access features only available in a more advanced version.

If it doesn’t seem like you can get the information you need to upsell at the right time, consult with your technical team to see if new analytics features can be added.

With the right data, you can tailor your upsell discussion to the specific needs the customer already has.

Upselling vs. Cross-Selling


While upselling focuses on upgrading a customer's solution, cross-selling is the art of finding new solutions that boost the usefulness of existing ones.

Since no “new” purchase is required, cross-selling usually introduces an accessory that’s separate from, but enhances, another product.

For example, retail brands that bundle a desktop computer and a printer at the same time are cross-selling. You could buy either one separately and each would still be useful without the other.

Upselling Tips and Strategies That Will Help You Sell More

Upselling 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.

Be Ready to Upsell in Customer Support.

Customer support reps, not sales experts, will capture the majority of 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.

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.

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.

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 upsell opportunity you should pursue.

Maximize Value in Ways Your Customer “Gets.”




When you introduce your upsell, 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.

Use Your CRM to the Absolute Fullest.

Your CRM is the best compass you can have for pointing the way to upselling opportunities.

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.

Integrate Cross-Selling Into Your Upselling.




Upselling has a bigger place in the business model of most companies than cross-selling, especially once customers reach maturity. Still, both approaches to selling have their place in the big picture.

By being alert to the ways your products work together and how they can add value in different situations, you’ll be more likely to recognize chances to strengthen a given account.

Every time you do that, you’ll not only help your customers to excel, but also deepen brand loyalty.

You can formalize your approach to upselling by making sure related questions are consistently used on your discovery calls. Once a customer is on board with your solutions, check the account status every now and then for telltale signs showing it’s time to upsell.

After the initial sale, cross-selling means you have to be perceptive. Check in with customers now and then – on account “anniversaries” and after trigger events – to keep them informed about purchases that could meet their changing needs.

10 of the Best Upselling Examples

Your clients already know they get value from your existing solutions. It’s much easier to help them see potential in what they’re familiar with now than to take them on a whole new journey.

Naturally, upselling is a significant part of the business plan for software companies and other solution-focused businesses. However, it can also be seen in a wide range of other contexts.

Let’s look at 10 of the best upselling examples from well-known companies.

1. Dollar Shave Club

Dollar Shave Club

Dollar Shave Club is one of the best examples of upselling online. The name makes a promise that’s very attractive to most men.

When you reach the site, a beautiful and highly optimized landing page offers two pricey, value-added options in addition to the expected “dollar shave.”

2. Spotify

Spotify Upsell

Giving people up to three options makes them more likely to choose one of the pricier ones. In Spotify’s case, it only needs two: Free and Premium.

The options are compared side by side and, let’s face it, most people who sign up will simply forget to cancel their free trial.

3. Booking.com


Booking.com is a long-lasting contender in the competitive world of online hotels, flights, and travel assistance.

Visitors using it for its main functionality – as a search engine for hotels – will find themselves subtly presented with upsell options right alongside budget rooms.

4. Amazon


Amazon has mastered so much of the e-commerce game, and it’s no surprise they’re good at upsells as well.

Of course, almost any time you browse a certain product category, Amazon will give you upsells side by side. SquareTrade product protection offers pop up on many items.

5. Carbonite


Carbonite was one of the early leaders in secure data storage and is still a big name in the field.

It has a premium price point for most consumers, so it fosters loyalty with consistent offers to discount and prorate entire months if subscribers choose to renew early.

6. GoDaddy


GoDaddy is one of the most prolific web domain registrars and hosts. It has “no frills” options and focuses on a consumer who wants to keep things simple.

With that in mind, it offers bundles including website builder and email for its hosting packages. That’s one-stop shopping!

7. Dell


Dell was one of the first computer brands through the gate with a “Help Me Choose” feature, which furnishes customized recommendations based on info you provide.

This allows users to see all their options (including pricey ones) instead of gravitating toward the simplest ones.

8. ProFlowers


If you’re looking around ProFlowers, odds are good you want to make someone you care about happy.

This is the perfect emotional hook for an upsell and the site uses that every Valentine’s Day: Customers are presented with the Deluxe option for more flowers and a nicer vase.

9. Priceline


Another example from the travel industry, Priceline has innovated with the concept of an upsell that doesn’t happen until after checkout.

Instead of highlighting it right on the website, which might come off as a hard sell, the offer to upgrade and extend your purchases arrives in your email.

10. Apple Store

Apple Store

Upsells and cross-sells drip from every pore at the Apple Store. The user experience is pleasant, but it’s still a challenge to get out with just what you planned to buy.

From product selection to chart to post-checkout, the buying cycle is rich with reminders about the latest and best products.

Start Upselling to Up Your Game

While the odds of selling to a new customer are somewhere between five and 20 percent on average, approaching an existing one gives you fifty-fifty odds or better.

Integrating upsells into your overall sales method is an efficient use of time that pays huge dividends.

Done right, of course, every upsell is in keeping with the inbound way of doing things: You recognize where you can add more value for each customer and then present it to them in a way that fosters trust and deepens the relationship.

That makes upselling best for everybody.

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Baylor Cherry

Baylor Cherry

Baylor is an inbound specialist for Bluleadz. As a native Floridian, she enjoys soaking up the Florida sun, buying clothes she can’t afford, and dreaming about one day owning a dachshund.