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4 Upselling Techniques to Boost Customer Retention and Revenue

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Upselling can help you build better relationships with your customers. Here’s how to do it.

What comes to mind when you think of the word upsell?

For many of us, it might bring up images of sleazy salespeople trying to line their pockets by selling us extra stuff we don’t need.

And, unfortunately, sometimes that does happen.

(I once had a dealer try to sell me an $85 car wash on a brand new car. I wish I was joking.)

However, when used properly, upselling can actually bring you closer to your customers, while bringing you more revenue, better retention and lower churn.

But first: what is upselling?

And how is it different from cross-selling?

A quick explanation of the differences:

Upsell vs. Cross-sell

The definition of upselling is selling a more expensive version of a product that the customer already has (or is buying), or to add extra features or add-ons to that product. If I’m buying a 27” TV and the salesperson offers me a 32” TV or an extended warranty, that’s an upsell.

The meaning of cross-selling is selling products that are different⁠—but possibly related⁠—to the product the customer already has (or is buying). If I’m buying a TV and the salesperson offers me a Roku or Playstation, that’s a cross-sell.

Both methods are useful, and both essentially do the same thing: help the customer get more value from your business, and help your business get more loyalty and revenue from the customer.

For the purposes of this post, I’m going to use the terms interchangeably.

The Biggest Benefit of Upselling

Sales guru Jeffrey Gitomer puts upselling into perspective when he describes it as helping your customers win.

A reader asked Jeffrey for advice on how they could upsell him on a credit card product that was more expensive (and more valuable) than the one he currently used.

His simple response?

Tell me how I win. When I win, you win.

If you can make your customer feel like an upsell is helping them win, then you’ll both win.

Here’s an example: a couple of years ago, I checked into a hotel on a weekend trip with my wife. As we were checking in, the clerk offered me an upsell: would I like to add breakfast for two⁠—normally $49⁠—to my room rate for “just” $29?

I accepted without hesitation, and I was happy to do so. At $20 cheaper than the standard rate, I felt like taking the upsell offer was an easy win.

From the hotel’s perspective, they upsold me on additional services that I otherwise would not have purchased, made extra profit, and built a deeper relationship with me, as that breakfast is one more opportunity that they’ll get to serve me.

A clear win for them, too.

In addition to the customer loyalty upside of upselling in customer service, there’s also the bottom line benefit.

In the book Marketing Metrics, the authors share a fascinating finding from their research:

The probability of selling to a new prospect is 5-20%. The probability of selling to an existing customer is 60-70%.

In addition to the customer loyalty upside of upselling in customer service, there’s also the bottom line benefit.

That’s a big gap.

But when we think about it, it really shouldn’t surprise us.

Wouldn’t we much rather buy from a company we already trust than one we’ve never done business with before?

Not only is upselling easier than selling to a customer for the first time, but it can help you grow faster.

4 Techniques to Include in Your Upsell Strategy

Use these tips to build your upselling strategy, each one ready to deploy at the right time and place:

1) The in-product upsell

When you approach the end of your available storage space in Dropbox, you’re prompted to upgrade each time you check the amount of available space in the app. And when your Dropbox is full, you can upgrade right in the app:

Offering the upsell within the app⁠—at a relevant time and place⁠—helps customers know and remember that a solution is readily available when their problem appears.

Takeaway: In-app upsells, as long as they make it clear why the customer will win by taking them, can be an effective way to not only increase revenue, but engagement, too.

2) The shopping cart upsell

This is, by far, the most commonly used method of upselling in eCommerce. But there are good and bad ways to do this.

When you order flowers from 1-800-Flowers, you’ll get some simple upsells that are relevant and can help you send a better gift. For example, I get offered the option to add candy, balloons or a teddy bear:

As a customer, I appreciate that I can upgrade my purchase.

Compare that to the all-over-the-place upsell parade that GoDaddy throws at you when you buy a domain name. As conversion expert Neil Patel explains…

They could drastically increase their conversion rate if they offered upsells that were more related to the product you just purchased. For example, I added a domain name to my checkout, and they offered me this product in the picture below.

Why would they offer you a website seal when chances are you don’t even have hosting, a website or even web traffic? I don’t know about you, but I’ve never built a website before I acquired a domain name.

Takeaway: The point of purchase is the most common upsell point for a reason: it works. Customers are in “buying” mode with their credit cards out, and ready to do business with you.

3) The support interaction upsell

Before we killed our Live Chat app, we offered it as a way to help customers faster and stem the flow of emails for customers who got too many messages. It was an upsell that was popular with our customers because it helped them solve a problem that they were contacting us about, and added additional value on top of that (by helping them offer additional value to their customers).

Now, of course, we offer one of our partner chat apps, but the value proposition for the customer remains much the same.

Takeaway: By offering an upsell that can help solve your customer’s support issue, you can help them, and your business, win. Note: upsells should never replace support, as in: if you can solve the problem without an upsell, do it.

4) The milestone upsell

Ramit Sethi sells online courses for people looking to succeed in their careers, personal finance, online business and productivity. With multiple courses, he has a lot of opportunities for value-add cross-sells.

One of the ways he delivers these offers is immediately after a customer success milestone.

Once a customer completes one of Ramit’s courses, they might receive an email that looks like this:

In it, Ramit offers an upsell⁠—with a free month-long trial⁠—to his membership program. It comes at an opportune time: when the customer is feeling good about the success they’ve achieved.

Takeaway: Target your customers for upsells when they hit customer success milestones, and when the value of your product is most apparent.

Ethical Upselling Is Good for Your Customers, and Good for Your Business

Upselling is a valuable skill for anyone delivering customer service, because it can help you achieve your number one goal: make your customers happier and more successful.

It’s not always appropriate (never sell to angry customers), but often it can help both you and your customers win.

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About the Author

Len Markidan heads up marketing at Groove. He’s focused on helping startups and small businesses build better relationships with their customers.

Read his latest posts or follow him on Twitter

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