Upselling and Cross-Selling: An Effective Guide

Cross-selling and Upselling are among the powerful sales and marketing strategies that help you to boost your sales conversion. 

Especially through email marketing, you can even double down on your cross-selling and upselling marketing techniques. 

The aim of these strategies is to get the best or the most from your customer. It promotes repeat purchases and loyal customers. 

Not just it, you can also improve the customer experience through upselling and cross-selling techniques, but with it, you also need to increase engagement as well. 

Here’s how you do upsell and cross-selling using email marketing campaigns and make the most out of it. 

What is Cross-selling? 

Cross-selling is a marketing or sales strategy when marketers or brands use a sales opportunity to sell additional products or services to their current customers.  

It is a marketing strategy to sell additional items to customers who either have already purchased from you or are purchasing at the moment. 

It is something like when you’re going to buy pizza at the store, and you end up having coke as well because the counter guy or pizza store encourages you to. 

Something similar happens in online shopping as well. Customers buy a particular product, and they are recommended to purchase a few other products along with it. 

What Is Upselling? 

Upselling is different from cross-selling. It is a sales or marketing technique that utilizes a sales opportunity to sell your existing customer an upgrade or more expensive version of the product or service. 

This is when you go to buy a hosting plan for your business website, and you choose a particular plan to go, but the sales guy pitches to you how profitable it will be to get a higher-cost plan as it has more value. 

Or, taking the same pizza example, when you go to buy pizza but end up buying a meal that includes more items and costs more as well. 

Why Do Businesses Use Cross-selling & Upselling Techniques? 

Well, to begin with, cross-selling and upselling is traditional and long-time existing marketing or sales strategy. 

You may pay attention or not, but it has been happening ever since. It is, in fact, one of the effective ways to increase sales for retail stores. 

One of the other reasons why cross-selling and upselling are used is it is way easier to sell to an existing customer than find a new one. 

In other words, it increases the average order value per customer. So you will be earning more from a particular customer, so even with fewer purchases, you gain more profit. 

According to the book Marketing Metrics, the chances of selling to a new prospect is something in between 5% to 20%, which is not so promising. 

Whereas selling to an existing customer has a higher chance as 6o% to 70%, makes it a lot easier to cross-sell or upsell them. 

You may wonder, why do existing customers have higher chances of buying with you again? 

Well, these can be some reasons : 

  • These customers are ready to purchase, buying-intent prospects. 
  • These customers have trust in your brand and product. 
  • They already established communication or relationship with you
  • Since they are buying or buying from you, you’ve got momentum on your side.
  • They are more receptive to your proposals and open to consideration. 

Another great benefit of them being your already customer is you have their email address, so the communication becomes way easier. 

Here comes email marketing to send them cross-selling and upselling emails consistently, where you have higher chances of conversions as compared to other new prospects. 

So, let’s overview the benefits of cross-selling & upselling 

  • It increases the average order value on your purchases 
  • It increases your company’s profits 
  • It reduces your customer acquisition cost due to a higher ROI per customer
  • It improves customer retention
  • It encourages customer loyalty 
  • It promotes brand awareness by sharing your products and offers 

Cross-Sell Vs. Upselling 

A lot of marketers get confused between cross-selling and upselling and also about their required usage in specific situations. 

To begin with, here’s what differentiates cross-selling from up-selling at a conceptual level which you first need to get clarity on. 

Cross-selling is more of an e-commerce practice where online sellers or retailers encourage their customers who recently purchased or are about to purchase to buy some additional products. 

The goal of cross-selling is to increase the average order per value per customer. On the other hand, upselling is a simple strategy to suggest to their users or existing customers to upgrade their products. 

Let’s take a case and try to understand how cross-selling and upselling strategies will apply to them differently : 

Case: Suppose a user just added shoes to their cart on your website. 

Crossing-Selling: Show them product recommendations at a lower price for the shoes but highly relevant to them, such as socks, shoes, or other shoe care products. 

Upselling: You need to suggest more or similar shoes but more expensive than they are choosing or going to choose. 

Let’s take another case for an example by drawing a comparison of how cross-selling and upselling work.

Case: A user wants to buy a smartphone from your website 

Cross-selling:  When the user is buying the phone, you can offer them more products such as headphones, a phone cover for that handset, a screen protector, etc. 

Upselling:  Show them better alternative smartphones with a larger screen, better cameras, and more features, hence higher price 

How And When To Cross-Sell? 

Cross-selling doesn’t come up with a guidebook or set rigid rules, not even what you are habitable to see with marketing strategies or sales strategies. 

You can cross-sell in any way you want, only if it needs to work. 

Cross-selling at its core, is about knowing your customer so well, the behavior that you suggest, and encouraging them to buy more products that complement their existing purchase. 

Again, cross-selling usually works when it is done in favor of your customer. When they really need to buy or have enough reason, only then will they buy it. 

Average Order Value 

Basically, it is a way to increase the average order value per customer. 

It means if you are selling to five customers a day, earning 100 USD, cross-selling and upselling can help make the same number of sales per day but with more purchases per customer.

So this means, selling to the same five customers per day, you might earn 150 USD per day or 180 USD per day even. 

Average Purchase Frequency 

Another factor that plays a crucial role in your average purchase frequency is how often customers purchase from you or how long it takes to buy from you. 

Cross-selling when your customer has already received the product won’t be as much as effective if you do it at the time of their purchase only. 

At this time, you have a higher chance of a conversion. Lower purchase frequency means a lower conversion rate for cross-selling. 

In this case, it will be better to send them the cross-sell email just after they bought your product or made their order. 

Suppose the average purchase frequency is less than 30 days; in this case, you can certainly send them product recommendations based on their previously bought products.

Delivery Fee & Time 

How much time you take to deliver your product to the customer also impacts your cross-selling strategy and timing. 

The same with the delivery charges as well. According to these factors, you have to decide whether you will be cross-selling through emails after the delivery or before. 

If delivery time takes more than ten days, then it will be better to send them cross-sell emails before the delivery. 

But if you are delivering the product the next day or within 3-4 days, you can send them a cross-sell email like product recommendations or products you will also like after they get delivery. 

The best scenario is to experiment and test with different circumstances and see what gets you more engagement and conversions. 

Best Email Marketing Tips For Cross-Selling And Upselling 

best email marketing tips for cross-selling  upselling 

Make Sure To Segment Your List 

Your email list includes all kinds of contacts : 

  • Prospects
  • Potential customers 
  • Blog readers 
  • Previous customers 
  • New customers 
  • Cart abandonment users 

And much more. 

Have a look at 10 Email Segmentation Strategies For Beginners To Try Now

And to effectively cross-sell and upsell, you need to find the contacts from your email list who are your existing customers. 

So, clearly, you have to segment your list on the basis of criteria as new customers or recent customers bought from you. 

By categorizing the new customers and existing customers, you will be able to customize your email content to be more relevant. 

You will be able to customize your content to achieve more open rates, engagement, and, more importantly, conversion. 

This also means you can do extensive research and organize these customers even further into sub-groups for more accurate targeting and personalization. 

When you create customized and personalized content for this segmented list, you will be able to send exclusively specific emails to them. 

You also will be able to send them complimentary products & services. Segmentation helps you to send them more personalized emails regarding upselling and cross-selling. 

Segmentation helps you increase open rates,  conversion rates, and click-through rates with a significant increase.  

Make Cross-Purchasing Easy For Them

When you’re cross-selling, it should be easiest for them to add those products to their cart and reach the payment page immediately. 

People order online because it is quick and easy for them to do, so cross-selling must not be complicated or require too much process in-between. 

Amazon is one of the best examples which do cross-sell at various levels starting from the product page itself, where it suggests a particular combination to buy instead of just that one product. 

Then, it even shows related products as well to give them alternatives. Adding these products to the cart is just one click away. 

For cross-selling, they should not need to put their payment details again or any more details. The more swift and fast this process will be, the chances are they will end up buying additional products. 

Also, making this process will directly cost you those customers who will be buying on impulse because then will be obstructed and slowed down to not buying it eventually. 

Be More Helpful To Your Customers 

Helping your customers increases not only the engagement rate but also establishes your brand as more reputable and caring. 

Promoting your products or services need to be subtle and very relevant. 

It should be, in fact, really something that your product or service can help them, then only recommending it makes sense and actually works. 

Upselling or cross-selling won’t work if you are just aimlessly recommending them to spend more or upgrade their product, plan, or services. 

It needs to have a valid reason. You can’t be pushy. Don’t be a car salesman relentlessly bragging about a car’s features and pushing them to buy it. 

Be that friend who couldn’t stop himself talking about how amazing that tool has been for them. 

Focus on actually helping them, and in the way, you need to find the right spot to plug your product or upgrade makes perfect sense why they need additional products. 

However, if earlier you sold something on the value you’re providing and built a relationship with them, then cross-selling and upselling do become a bit easier. 

Be the industry leader and help your customers to resolve their respective problems through your product or services. 

Being helpful, engaging, and the patient will instill enormous amounts of trust in you and your brand; chances are you won’t even have to make a hard sell there. 

Helping them through tips and strategies will somehow bring you the opportunity to genuinely introduce the additional solution as your product or service. 

Have a look at What You Should Know About Customer Journey Mapping? 

Learn to Pair The Products 

Understanding which products are to cross-sell with which particular product is essential for a successful cross-sell email campaign. 

You need to understand which products go best in pairs on the basis of relevance, accessibility, popularity, or any other factors. 

In fact, chances are if you regularly experiment with trying different pairings of products in the cross-sell, you get some of them working so much better than others. 

Those ones you need to repeat and boost your sales conversion. 

The idea is to understand when they add a particular product to their cart, and what other products or a product they are more likely to buy if you suggest them. 

And that’s what you work on regularly to find out the best pairing for successful and high-conversion cross-sells. 

Make sure you don’t force a particular pairing because that is not going to work anyway. In fact, that possibly be irrelevant and completely opposite to what cross-sell means. 

Make Sure To Have A Distinct Voice 

People choose a particular brand for multiple reasons. Definitely, the quality of the product, variety, and trust are some primary reasons. 

But a lot of companies offer quality and variety, and yet there are many brands to trust, so the real reason why someone purchases from a particular brand are the connection.  

They feel some level of reliability and identity through the brands. It is the connection they feel with them at some level; it can be familiarity or similar beliefs or ideologies. 

And primarily, it comes from the voice a brand communicates through to its prospects. It also extends to their emails as that’s the most intimate way to connect with their audience. 

Every brand has a distinct voice, the way they see things, interact with the audience, the kind of product they sell, why they sell, and much more. 

To really increase your sales, and also your upsells and cross-sell, you need to use a distinct voice in your email communication. 

Have a deliberate effort towards understanding how you interact with your audience. What kind of communication will it be? 

It depends upon the kind of brand you want to build, the type of audience you’re targeting, and the product you’re selling. 

Have a personality in your email communication. This way, you will be able to deeply connect with your audience, which means more engagement and conversions. 

Don’t Cross-Sell Every Item 

One thing you need to understand when you cross-sell, you might not feel good about leaving the opportunity to not be sold in a cross-selling campaign but not all of them are suited to cross-sell. 

You have to identify which products are more appealing to the customers as cross-sell products.

For this, you also have to see which of your products are the best-sellers and now have some selected low-cost and tempting products that compliment your primary products. 

Also, for that, you have to share your marketing efforts, so make sure which products you invest time and money to promote in your cross-sell. 

You don’t have to, want to, or should be selling every product to cross-sell; rather, choose on the basis of relevance and profitability. 

Make sure you monitor these emails and see how these products are performing as cross-sell products. 

Focus on the products that are selling fast with a particular prior purchased product. Identify the popular combinations that sell like hotcakes together. 

Make sure you create an email copy encouraging why they need these products. Keep checking the analytics and ROI you gain from these emails. 

Keep shortlisting the list of your top popular products and repeat this process to refine and improve better for higher conversions. 

Another reason why you should not cross-sell every product is that sending all of your products multiple times to your customers feels like you’re spamming them. 

Get Strategic With Your Timing 

The timing is everything when it is about cross-selling and upselling. You cannot approach customers anytime for both of these sales techniques. 

It has to be particular timing when you approach them and that increases the chances of sales conversion you get. 

For example, if an amazon customer recently bought a smartphone, they will receive emails regarding additional products to buy, such as smartphone covers, earphones, etc. 

The accessories and items that are usually needed with a smartphone or someone might be interested in buying after buying a phone. 

But the timing here is crucial; within a few hours of purchasing it or receiving the items, they are still in a buying-intent zone. 

After a while, they might not be, especially after a few days or months. So Amazon approached them to upsell through multiple products a few times. 

First, on the product page itself, suggesting to buy products in combo, again in the add-to-cart page suggesting similar products, and then again through their emails, sending their best offers. 

You have to identify the gaps between their current usage of products and the requirements of the complementary products. 

Don’t Be Greedy With Cross-selling

The #1 mistake usually the newbie marketers or business owners make with their cross-selling emails is they get greedy with it. 

If there is a customer that bought a product from your site worth 200$, you wouldn’t want to cross-sell them with a product worth 800$. 

It is common sense to understand the simple fact that you don’t go to a store to buy a smartphone back cover, and then you buy a smartphone thinking that you will need it. 

It’s always the other way around. The whole point of cross-selling is to increase the average order value by suggesting to the customer the related products. 

But usually, they are the items that are related to their primary product but cost way less than that, so they feel like buying it. 

Cross-sell products come from impulsive buying or the fear of missing out on a customer usually when they feel compelled to buy more than one product after their purchase.\

Remember, cross-selling items are usually low price items that they feel comfortable buying considering they made a heavy-cost purchase right away. 

So cross-selling is about recommending lace packs and socks to a customer who just bought shoes; you don’t get greedy and offer them another shoe or shoe rack itself. 

Put A Clear Call-to-Action 

When you upsell or cross-sell through email marketing, you need to make it clear what they are going to get from it. 

But more importantly, put a clear CTA in your emails, so after getting convinced why your customer needs an upgrade or why another plan is way better for them than they’re currently using, they would know where to click, and for what. 

You can also lay out a problem for your customers regarding their existing product, something more personalized with a solution. 

Make sure they know what next step they can take to make it better and what exactly you’re offering them to do. 

Leveraging Email Marketing automation 

Email marketing automation can make your upselling and cross-selling email practices highly efficient and consistent over time. 

When you regularly send highly personalized emails to your segmented contact lists of customers regarding upselling or cross-selling at the right time, you will be consistently getting some sales over time. 

Don’t forget to experiment, change your offers and get more personalized offers into the mix to improve your sales conversion. 

Best Cross-selling Examples

Cross-selling is even more effective than upselling, especially for online retailers or if you’re a brand with multiple products.  

Here are some of the best cross-selling examples that you can learn from and apply to your email marketing strategies as well as marketing strategies too. 

Frequently Purchased Items 

This is something predominantly seen on Amazon stores where on the product page, it will advise the potential customers to add more products. 

It recommends specific products, one or two more offering them as a combination with existing products suggesting that they are frequently bought together. 

Now using the term ‘frequently bought together’ gives this idea that people usually buy all these products together, so it might be more useful. 

This bundle offer subtly signifies that customers will miss out on these products if not bought together through social proofing and using fear-of-missing-out. 

The same technique you can use further in the emails, same as Amazon uses through their product confirmation emails. 

At the bottom of the email, they add a column with the title ‘Customers who bought (name of the product they bought) also bought these….” 

At this slot,  more product recommendations are offered as frequently purchased items. 

Recommendations In Post-Purchase Emails

Sending out recommendation emails should be more personalized towards your specific targeted users. 

Depending upon their purchase history, search history, wish list, and other data from your subscribers, you can create a list best suited for them to purchase from. 

Image Source: Targetbay

Sending them recommendation emails is another way to cross-sell your buyers who just bought a product from your store. 

These products are better related to their primary products, which they might need. 

For example, Beauty & Tailor sends out this ‘thank you email where they also put product recommendations in the section of ‘You May Like. 

Image Source: SaleCycle

Another example is Matalan, who very cleverly picks up the relevant products to the previous purchase of a buyer into their post-purchase email. 


Another popular cross-sell example has to be the reminder email sent to the subscribers to add more products to their cart before you ship them. 

This can be done in all different ways where you can send a customized offer where adding one or two products amongst the given list get some good discount. 

Or give them a bundled price post-purchase for adding more products to their bought items. 

Dollar shave club, a brand known for its interesting marketing efforts, takes the informal approach to this without being pushier or sell-say about it. 

Image Source: Sendpulse

They send a cross-sell email with updated information regarding their shipment for the product they already bought. 

But right there, without pushing them, they just suggest some similar or related products to ‘toss more in’ as they put it before they ship their product. 

Make sure you give more of a ‘hey don’t forget this’ or ‘check this out too’ kind of vibe to make it light-hearted and casual. 

Personalized Recommendations

You can always get more personalized with your recommendations and suggestions to your customers through your cross-selling emails. 

Whether the buyer just has bought a product, and you delivered them, or it is in transit, and even if it has been a while, cross-selling personalized recommendations are effective. 

Just make sure you put some good effort to really nail the products they really may like on the basis of their history, email marketing tools, and other marketing technologies.

Image Source: Clear voice

This is how Sephora, a leading beauty and cosmetic brand, does it with their recommendations emails. 

You also have to make sure that you only put 2-3 products in there ideally or at max 3-4 since it should be hand-picked or custom selected for the customer only. 

In fact, suggesting even one product every week also works. It depends upon what kind of products you’re selling. 

Best Upselling Examples:

Urgency-driven Upselling 

Leveraging the FOMO (Fear-of-missing-out) of your customers to induce urgency for quick purchase or up-gradation is a highly effective technique. 

The same kind of marketing technique is utilized with upselling to upgrade the plans or products that your customers bought. 

Image Source: Sendpulse

One of the best examples is Evernote sending these upselling emails to their customers, where they help overcome the customers’ doubt and encourage them towards action. 

Their emails give a set limitation of time to their customers where if they upgrade now or under a  particular time limit, they will get an extra six months on their subscriptions for free. 

Image Source: Moosend

Take the example of Audible, which understands how confusing it is to choose one book from their audio library, so much so that it gives decision paralysis to customers to pick another. 

Hence, they start recommending their customers their next listen just with their previous order confirmation.

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