7 Techniques for Mastering the Upsell & Boosting Customer Buy-In



Have you ever played Starcraft? And what about Civilization? Or any other computer strategy game for that matter? 

In these kinds of games, you basically control the growth and evolution of a society. 

In order to grow, you need to mine and collect resources. Lumber, ore, food, stones—you know, the building blocks of any great civilization. 

And like so many other games, the end goal is usually to dominate the other societies on the map. 

Now, a lot of people make the mistake of focusing all their efforts on boosting military power first thing. But the truth is, upgrading your ability to mine resources better is the key to success. Because when you focus on that, you can get more lumber out of a tree. More stone out of a quarry. And more ore out of a mine. 

You’re getting more value out of the same resource

And that lets you grow, advance, and thrive faster than the other societies you’re competing with. 

Upselling is like upgrading your business’ ability to mine value from your customers. It lets you earn higher revenue per client. And that means you don’t have to spend nearly as much time on finding new clients… when you do it right

In this article you will learn how to master the art of upselling, why they work, and how they help you get more value from fewer customers.

So let’s start skyrocketing your customer value with upselling right now!

What is an Upsell?

Before getting into how upselling can help you boost your business, let’s make sure we understand what an upsell is. 

Here’s a quick definition we go by here at AutoGrow: 

An upsell is a technique where you entice a customer to buy more. You can do this by providing upgrades, expensive items, or other add-ons to their purchase to increase the dollar amount of the entire purchase.

Simply put, an upsell is just a way to increase the value of each customer. It accomplishes that goal by getting a customer to buy other products or upgrade to higher value ones that you offer. 

There are two main ways of incorporating upselling into your business. 

1. Increase the Average Order Value (AOV) by getting clients to buy other products or upgrading before checking out. 

2. Increase the Customer Lifetime Value (CLV) by getting clients to buy other products or upgrading after checking out (this is where a solid email nurturing campaign comes in).

Why Do I Need to Start Upselling? 



It makes you money. Why else do you do anything in a business? 

Upselling increases the value of a customer. Whether it’s by boosting their initial purchase value or by increasing the lifetime value, the end result is still the same: your customers will be worth more. 

But what makes upselling different is the fact that it’s often an especially simple and cost-effective way of increasing the value of a customer. 

For example, we’ve all heard the old saying that it’s more costly to get new customers than to retain old ones. But do you know just how huge the difference is? 

Some estimates put it at being 5X more expensive to find new customers compared to selling to older ones. 

In fact, boosting customer retention rates by just 5% has been shown to lead to profit increases of 25% or more! That’s because returning customers have a higher CLV. They’re easier to sell to, often have a higher AOV when they do buy from you, and they are a great source for referrals too. 

Okay, so increasing retention is great for business. But what a lot of businesses don’t take into account is that boosting monetization of current customers also comes with a huge ROI boost

We covered this in another post about upselling but it’s worth repeating here. 

In a study of 512 different companies, Price Intelligently, a pricing strategy company, found that increasing monetization of current customers is the fastest route to boosting profits. 

As you can see from the graph below, improving the AOV (monetization) of customers by just 1% can lead to a 12.7% increase in profits

Retention came in second with a 6.71% profit boost per 1% improvement and acquisition was dead last with just a 3.32% increase. 


Source: Price Intelligently

The main takeaway here is clear: increasing the AOV and CLV of customers is more important than bringing in new ones. 

And upselling is the best and easiest way to do both.

Upselling vs. Cross-Selling

There’s usually quite a bit of confusion surrounding this question. And in fact, a lot of the time people just use the two terms interchangeably. I’m guilty of it myself. 

Now, in most cases using the wrong term here won’t be the difference between life or death. 

But when you get down to the nitty-gritty of it all, there are some distinct differences between the two. So let’s take a look at just what those differences are. 

  • Upselling: This is technically when a business or service offers an upgrade to a product that a customer has picked out. Take AutoGrow for example. Our instant Done-For-You funnel marketing team’s Ultimate Package is our most popular. But we also know some clients will get more value out of the Supreme Package. So we send out an upsell email describing the benefits of switching to the Supreme Package so our clients understand if it’s a good fit for their business. That’s an upsell
  • Cross-Selling: This is when you offer a different product or service to a customer after they’ve already chosen what they’re buying from you. Amazon does a great job at this. There’s an entire section of every product page that shows you what other products are frequently bought together with the one you’re looking at. If I look at a baseball glove, for example, it also shows me baseballs and glove oil, right on the same page! There are even a few buttons right there so you can add them to your cart with just one click. That’s cross-selling. 


There are plenty of other examples of upsells and cross-sells out there today, especially as e-commerce becomes the main way we shop today. 

And honestly, distinguishing between the two isn’t as important as understanding what both accomplish, which is increasing the value of a customer. 

3 Reasons Why Upselling/Cross-Selling Works

Upselling and cross-selling are two of the best ways to boost monetization and retention of customers. And as we’ve seen, focusing on these two areas in particular can increase profitability by 3-4X more than concentrating on customer acquisition. 

But why do these tactics work? Why do people respond to them? And what is it about these techniques that make them irresistible when done right? 

There are 3 reasons here...

  • Emotional Excitement: First and foremost, there’s the thrill of buying! Okay, so emotions may not be running too high when you’re purchasing a new loofa or a pack of undershirts. But there are two things in particular that bring out our emotional side when buying: the promise of a better you (smarter, sexier, funnier, happier, whatever!) and cashing in on an exceptional deal (high value for low cost). Upselling taps into those emotions from the original product and makes them even stronger. They’re taking what makes you feel good about buying and giving it a boost along the way. 
  • Already Spending Money: The hardest part about spending money is… well, first deciding to spend money. There’s the guilt, the uncertainty, the skepticism—it all adds up to you asking yourself, “Is this really worth it?” But when you’ve already barrelled past those obstacles once, it makes it so much easier to keep on doing it. Once you’ve actually decided to spend money on a purchase, you’ve broken down the floodgates. And making an additional purchase (as long as it has value) is going to be easier than deciding to make the first. 
  • Trust Is Built: Finally, once you’ve built up trust with a customer, it’s far easier to sell to them again and again. One of the most commonly pointed to stats here is from Marketing Metrics. It says, “The probability of selling to a new prospect is 5%-20%. The probability of selling to an existing customer is 60-70%.” That’s because you’ve already shown past customers that you deliver value. And once you’ve done that, you become a trusted source of quality products or services. All that’s left now is maintaining that trust.

7 Things to ALWAYS (and NEVER) Do When Upselling


So, now that we know what upselling is, why to do it, and why it works, let’s take a look at 7 tips for upselling the right way. 

1. ALWAYS Add Value 

If there’s only one thing you should take away from this article it’s that an upsell should always add value to your customer. 

Offering value is the key to getting your customers to sign on to buying more from you. 

And one way to make sure your customers are getting value from the products you’re offering is by choosing upsells that are relevant. This is especially important with cross-selling.

If you’re offering a course on marketing, for instance, a good cross-sell would be a collection of case studies outlining the best conversion optimization techniques like our Proven Sales Conversion Pack

The more relevant you can make your upsell or cross-sell offer, the more likely your customers will be to buy. 

2. NEVER Make It Meaningless

In the same vein as the last tip, don’t ever throw in products just for the sake of including an upsell. 

Upselling is first and foremost about increasing the value of a customer. 

But trying to get your customers to add on something that’s completely irrelevant to who they are and what they’re trying to do is a quick way to lose trust. Plus, it makes your brand seem a little scummy. 

So not only will your upsell probably not perform that great, but it’ll also knock your reputation down a peg too. And that can spell out trouble for keeping your customers loyal. 

3. ALWAYS Add Upsells During Checkout


Adding in upsells and cross-sells during the checkout process is a great way to increase AOV.

And you see this tactic everywhere where money is being exchanged. At the supermarket, on Amazon, at the gas station. That’s what all those mouthwatering candy bars are doing there in the checkout line!

They’re there because putting impulse buys at the end of a shopping experience gets people to buy. Throwing in a few relevant and useful add-ons to your checkout page is a quick and easy way to up the average order value of your customers. 

However, you don’t want to abandon the upsell best practice of making your offers relevant

Even if your offer is an impulse buy, you don’t want to do anything to poison the customer trust you’ve worked so hard to build. 

4. NEVER Make Their Prices Disproportionate

You never want to make the price difference between the original product and the upsell too high. 

Because if you do, no one is going to end up adding it on to their order. 

That’s because they’re already prepared to spend a certain amount once they’ve reached the checkout line. And if the price of the add ons you include is as much as the original product, it’s going to immediately seem like a bad offer. 

Instead, aim for a smaller price difference. Some experts say 25% of the original price is the sweet spot. Others claim 40%

In the end, though, the best thing you can do is A/B test what’s right for your business and your products. 

5. ALWAYS Follow Up With Emails (Seriously… ALWAYS)


Never miss a chance to follow up with past customers via email. 

Building and maintaining an email list is without a doubt one of the best ROIs in the industry. In fact, some estimates but the return on investment as high as 3,800% according to Hubspot.

That’s because email is a direct avenue of speaking to your customers. 

  • You can nurture the relationship by sending them content they’ll get value out of. 
  • You can clue them in to special promotions you’re running right now. 
  • You can show them the value of upgrading their current plan. 
  • And you can increase their CLV by cross-selling other products that they’re sure to enjoy. 

Just be sure to make things relevant and useful by personalizing each email. Otherwise, you may be doing more harm to your relationship than good. 

6. NEVER Resort to Sneaky Tactics

We’ve all seen those upsell pages that pull out all the superficial stops to get you to buy. 

The bright colors, the flashing lights, the bolded and uppercase fonts. They’re annoying, right? 

They reek of desperation. And they certainly don’t change your mind and get you to buy in most cases. 

But what’s even worse than that is using sneaky tactics to get your customers to add an upsell. 

Tactics like making it harder to decline your offer with hidden “No Thanks” buttons. Or wording the copy in such a confusing way that visitors click to opt out only to find they’ve actually been signed up for the add on. 

Do not do this. Doing so can instantly devastate the trust you’ve built with your audience this far. 

And even if they do end up signing on to purchase the upsell, they likely won’t be coming back to buy anything from you again. 

7. ALWAYS Try to Bundle Your Upsells When You Can


Bundling is a great tactic used by marketers in nearly every industry. It’s when the specific features and details of your product or service are included in one over-arching price rather than separated out. 

AutoGrow, for example, includes Copywriting, Quality Assurance, Graphic Design, Strategy Sessions, and Ad Management in all of our monthly packages of our Done-For-You sales funnel service without calling out the individual costs of each. 

In addition to this saving us a heck of a lot of time pricing each (after all, each is 100% integral to delivering a polished and high-converting end product), it also makes it easier to get buy-in from clients. 


Because bundling actually triggers fewer pain points than seeing the costs of each feature. Instead of 5 price tags, clients only see 1. And for many, that’s a much easier pill to swallow.


Upselling is one of the best ways to increase the AOV and CLV of your audience. And at the same time, incorporating upselling/cross-selling into your business is actually more cost-effective than spending money on bringing in new customers. 

If your interest is piqued and you’re looking to start upselling (and honestly, why wouldn’t you be), there are 7 things in particular you can do to make it more successful...

  • ALWAYS Add Value
  • NEVER Make It Meaningless
  • ALWAYS Add Upsells During Checkout
  • NEVER Make Their Prices Disproportionate
  • ALWAYS Follow Up With Emails (Seriously… ALWAYS)
  • NEVER Resort To Sneaky Tactics
  • ALWAYS Try To Bundle Your Upsells When You Can

And if you do all of those, you’re sure to see a hefty bump in your bottom line thanks to your upselling efforts. 

How has upselling improved your business? What techniques, in particular, have you used that have gotten you results? 

Let us know in the comments below. 

And as always…

Keep funnelin’, stay focused,

Alex T.


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