10 Best Upsell Email Examples and What Makes Them Perfect

Upsell emails can lead to a 10-30% increase in revenue, which makes them a vital part of any email marketing strategy. 

In this article, we’ll go through all the little details you should know to make a perfect upsell email campaign: from best moments to send upsell offers to 10 effective upsell ideas packed with real-world examples.

Upsell Emails vs Cross-Sell Emails: What’s the Difference?

You should think of upsell and cross-sell emails as powerful tools designed to encourage additional purchases and, as a result, enhance customer lifetime value. While both aim to increase revenue, they do it through different strategies and focus on distinct aspects of customer behavior. 

So, what’s the difference?

When to Send Upsell Emails for Better Effect

As with any other marketing activity, timing is crucial here. Let’s dive into 5 situations when upsell emails may significantly enhance the effectiveness of your email marketing strategy.

1. Post-Purchase Window

When to send: 1-7 days after purchase

At this period, the recent purchase is still fresh in your customers’ memory and they are still excited about your product. It’s a perfect moment to introduce them to a higher-tier option.

For example, you could suggest switching to a premium (and more expensive) plan at a discounted price.

2. At Renewal or Subscription Time

When to send: a few days before subscription renewal 

If you sell subscription-based services, use the period leading up to a renewal to suggest an upgrade. At this moment, your customers are probably analyzing the value of their subscription, so you should grab this chance to showcase how an upgraded plan can provide even more benefits.

Note that the time of sending depends on the type of the subscription. 

Take a B2B yearly subscription that costs $10K, for example. It’s unlikely that someone in your client’s company can make such big decisions alone. So if you want to make an upsell, give your clients enough time to discuss the offer with decision-makers.

3. During Special Events or Milestones

When to send: on customer anniversaries or during major sales events

Special events are an excellent opportunity to upsell. People expect to receive email campaigns offering gifts or discounts on their birthdays, customer anniversaries, Black Fridays, and other major events. So why not grab this opportunity to upsell your products/services?

4. When Introducing New Features

When to send: immediately after launching new features

Whenever you introduce new features or make significant improvements to your product, it’s an ideal time to upsell. Customers are usually curious about updates and might be willing to pay extra to access premium features.

And if you promote some complex tool, a good idea would be to invite your customers to a demo call (with a potential upsell).

5. After Customer Support Interaction

When to send: within 24-48 hours after resolving a support issue

56% of people say that successful customer service influences their loyalty to a brand more than any other factor. So you might want to send an upsell email after a positive customer support interaction, as your clients would probably feel that you care about them.

And if you can think of a reason why a more expensive pricing plan will help customers avoid problems in the future, that could be your perfect selling point. 

10 Best Upsell Email Examples and Why They Work

You’ve learned the key differences between cross-selling and upselling emails as well as the best time for an upsell offer. Now let’s analyze 10 email marketing ideas along with real-life upsell email examples that will help you create a top-notch campaign.

1. Tell Subscribers About the Advantages of a More Expensive Plan

Customers are often willing to pay more if they understand the benefits of the upgraded version. So you should clearly articulate the additional features and how they solve specific problems or enhance user experience. This way, you’ll encourage your existing customers to consider the long-term benefits rather than the immediate expense.

Meet AllTrails+: Premium features that fit your nature

This upsell email example by AllTrails clearly communicates the benefits of upgrading to AllTrails+ and provides multiple call-to-action buttons that encourage users to take the next step. The structure of the email makes it easy to skim through.

Another thing that caught my eye is the table comparing free and advanced features which provides a quick visual reference to understand the added value.

1 tip to make this upsell email even better: I bet AllTrails’ potential customers would love to see testimonials or reviews from current users to make an informed decision.

2. Emphasize How a More Expensive Subscription Will Save Customers’ Money

This upselling strategy works pretty well because it appeals to our desire for financial efficiency. If a customer sees that they can get more value at a lower overall cost, they are more likely to consider the upgrade. It works especially well with offers like “get a 20% discount for a yearly subscription” or “pay for 10 months and get 2 months for free”.

Get 60% off 3 orders and unlimited savings with DashPass.

DoorDash’s upsell email immediately catches readers’ attention with a powerful subject line and clear value proposition. When a person opens the email, the first thing they see is that they can get a premium account and save money at the same time (a tempting offer, right?). 

People love statistics, so I think the turning point for many people will be that DoorDash openly shares how much money its customers usually save every month.

1 tip to make this upsell email even better: I’d probably add more CTA buttons to this upsell email. It may not be the problem on a desktop, but if you’re using a smartphone (as most email readers do now), you’ll have to search for the button. 

3. Appeal to Emotions

We usually sell not just a product or a service, but the idea behind it. Such emotional appeals can build a strong connection between the customer and the brand, making the decision to upgrade feel like an obvious next step. Depending on your business, this could be the ideas of safety, simplicity, excitement, reliability, and so on. 

If you don’t know what emotion you should appeal to, run a series of interviews with your existing customers and ask what they associate your brand with.

Welcome to Citizen! Upgrade to Plus for an upleveled safety experience

Citizen sells the idea of safety in its upsell email (and does it really well). Bold headlines and contrasting colors draw attention to the key points. I believe that the focus on safety and customization of notifications is going to be highly relevant to Citizen’s target audience.

1 tip to make this upsell email even better: I love the design and the “features” section, but I would probably make the first text block more concise to improve readability and keep the user’s attention focused.

4. Offer Free Shipping

34% of customers usually refuse to purchase if they don’t get free shipping. So if you can make it part of your upsell offer, do it. This way, you’ll remove the friction point and make your premium membership (or product) more attractive.

Never Pay For Delivery Again

This upsell email by Postmates is short and simple, yet very effective. It comes with a very minimalistic design and clear value proposition which make it easy to understand the benefits of signing up.

What I also like is the bold “Never Pay For Delivery Again” subject line as it immediately grabs attention and highlights the primary benefit of the subscription.

1 tip to make this upsell email even better: what I would add is a link to more detailed information about Plus Unlimited (for example, about the duration of the free trial). This could help address any questions or concerns subscribers might have about the offer.

5. Compare the Functionality of the Free and Premium Plans

Another great upsell marketing strategy is to compare the features of the different pricing plans. This helps to justify the cost of the upgrade by making the benefits more concrete and understandable. 

Important note here: concentrate on how the lives of your customers will get better with the more expensive version (and not how bad they’re with the cheaper one).

45% OFF all plans! Upgrade to Premium and deliver your message with poise

This upsell email example by Grammarly is very illustrative. First, it gives subscribers a pleasant 45% discount on any Premium plan. To further enhance the offer, Grammarly shortly explains the benefits of Premium.

The brand doesn’t stop there and shares a comparison table that effectively contrasts the free and premium features, aiding in the decision-making process.

1 tip to make this upsell email even better: of course, the email is not very lengthy, but I’d suggest adding a couple of more CTAs to increase the number of conversions.

6. Offer a Free Trial Period

27% of US citizens say that a free trial period is what would motivate them to try a new brand. At the same time, the average conversion rate for opt-in trials (when users don’t share their payment details) is more than 18%. 

A free trial period lowers the risk for the customer. They can experience the benefits of the premium plan without an immediate financial commitment. If the customer finds value in the premium plan during the trial, they are more likely to convert to a paying subscriber.

Try Linktree Pro on us!

This upsell email by Linktree hints at the possibility of a free trial right in the subject line. And the email copy does its best to underline the message: from the “Upgrade today and save” headline to the “Start free 30-day trial” buttons. 

1 tip to make this upsell email even better: although Linktree mentions some of the premium features, they’re not easy to notice. That’s why I’d probably turn this section into a bulleted list to make the content more skimmable.

7. Use FOMO (Fear of Missing Out)

When you highlight exclusive features or early access benefits that are only available to premium members, that’s an illustrative example of FOMO. It encourages customers to upgrade quickly to avoid feeling left out, intensifying their desire to be part of a special group.

Unlock the top 3 premium Canva features 🔓

Another great upsell example is this top-notch email from Canva. The headline “Try everyone’s favorite premium Canva features” uses FOMO to grab subscribers’ attention and urge them to learn more.  

One extra great detail is the free trial offer, serving as a compelling incentive to convert users to premium subscribers.

1 tip to make this upsell email even better: personalized email subject lines are 26% more likely to get opened. At the same time, marketers notice a 20% increase in sales when they send personalized email campaigns. That’s why I’d suggest Canva use some simple personalization methods (e.g. address the recipient by name) in the campaign. 

8. Advertise a Limited-Time Offer

Limited-time offers (especially completed with countdown timers) create a sense of urgency and scarcity. They motivate customers to act quickly and take advantage of the deal before it expires. Combine the limited-time aspect with a discount or special offer, and you’ll make the upgrade even more attractive.

FINAL HOURS: Get 20% Off a Restream Upgrade

The first thing Restream’s subscribers see when they open the email is a bold black countdown timer against a bright yellow background. 

The email copy is pretty short and playful, and there’s nothing that would distract the reader from the main offer. I really like the “Trusted by” section, which showcases plenty of famous brands that use Restream’s services. 

And if that’s not enough to convince the most doubting readers, Restream mentions a 7-day money-back guarantee for first-time buyers. Very smart move when you’re confident about the quality of your product. 

1 tip to make this upsell email even better: I love this email a lot, but what I would definitely add is a small section describing the features customers will get when they buy the premium version. 

9. Offer a Relevant Gift in Exchange for an Upgrade

Gifts add immediate, tangible value to the upgrade. Customers feel like they are getting something extra for their investment, which can make the decision to upgrade feel more rewarding. So if you can think of a relevant gift you might offer, grab this opportunity!

It’s not too late: Free camera with Vimeo Premium

Vimeo uses an upsell email to promote the benefits of its premium version. The things that grabbed my attention are the “free Mevo” image along with the “Reminder” section that provide a strong incentive for potential customers. 

I like that Vimeo offers an alternative option (a 25% discount) for those who are not ready to purchase a Premium subscription yet. All in all, the email is visually appealing and easy to read. Good job, Vimeo!

1 tip to make this upsell email even better: Vimeo uses phrases like “it’s not too late” or “for a limited time only” to create a sense of FOMO, but I’d probably go a little bit further and include a countdown timer (or mention the exact deadline, at least) to make the offer more urging.

10. Advertise the New Top Features Available on the Paid Plan

When you’ve been using a product (especially a complex one) for quite a while and you’re satisfied with the results, you probably won’t go for a new one only because it looks more modern and has a couple of more features. 

However, when you search for a new tool, you’re likely to choose something that feels fresh and exciting. Your customers think the same way.

So, if you added some new features that would benefit your users, tell them about it! Customers are more likely to upgrade if they see that your product is continually evolving and adding valuable features.

Become a member to upgrade your apps

Our next great upsell email example is by Glitch. It’s relatively short but communicates the story behind the new features along with the benefits of upgrading. What makes the difference is that the email feels very approachable and community-oriented, as if you were reading a story from your close friend.

1 tip to make this upsell email even better: I love the simple email design, but it feels a little bit messy because all the text sections are of different sizes. So my recommendation here would be to use one font size for headings and another one for the main text. 

Key Takeaways to Remember

Upselling and cross-selling aim at increasing revenue, but they’re very different. Upselling is about selling more expensive products or services, while cross-selling is about selling additional goods. 

To maximize the effectiveness of your upsell campaigns, send them wisely:

• at post-purchase
• during subscription renewals
• on special occasions and milestones
• when a new feature launches
• after positive customer support interactions

No matter what upsell strategy you choose (highlighting value, creating urgency, appealing to emotions, etc.), Blocks is ready to assist you every step of the way! Start your journey towards top-notch emails today.