Upsell email examples that convert: How to woo your customers 

If you’re looking to drive more engagement from your customers, upsell emails are the perfect go-to. Of course, you’ll want to make sure that the upsell actually feels like a value-add to your customers—and that’s not always easy to do. By empowering customers to capitalize on what they’re already doing with your product, you’ll make your customers feel like the upsell is a logical choice.

Here, we’ve compiled our list of the best upsell email examples. You’ll see that each of these transactional emails thoughtfully moves customers into deeper levels of engagement. Each upselling example not only focuses on driving conversions in the moment but sets the stage for increased loyalty and customer lifetime value. Bonus? We’ve included a few of our own upselling strategies that you can borrow to build your own upsell email templates.

Upselling and cross-selling are related but different types of sales. Upselling encourages customers to buy a higher-end or higher-priced product, which is an upgrade. Cross-selling, on the other hand, sells related or complementary products—something along the lines of “You may also like.”

Once you understand the difference between cross-selling vs. upselling, you can spot the distinctions when you see them in the wild. Here are a couple of cross-sell email examples to highlight what makes them different from upselling techniques.

Purveyor of teas and tea-drinking accessories

Harney & Sons provides a classic cross-sell email example for a consumer product. You’ve purchased a product from the brand, likely something else in their Classics Collection. Based on your buying behavior, they suggest a related product you’ll enjoy.

Online learning platform for web developers

Here’s a less traditional example of a cross-sell. You’ve signed up for a targeted newsletter from SitePoint. Based on that behavior and what they know about you, they’re suggesting you check out a different newsletter! In this case, they’re not trying to get you to make a purchase, but instead vying for more of your attention.

You’re not replacing what you have; they’re simply offering you more value.

What’s the purpose of upselling emails, really? It might seem like a silly question—obviously, any business wants to increase revenue, and upselling does just that. But if you think about it from a bigger-picture perspective, upselling should serve a larger purpose: driving long-term customer loyalty and relationships.

With that in mind, here are five proven, effective upselling techniques to try.

1. Provide personalized recommendations. Your customer data is a gold mine of attribute and behavioral information you can use to personalize upgrade emails for each individual. For example, you might reference a specific feature the customer has clicked that isn’t currently available on their plan or even let them know when they’re about to hit plan limits. See how Musora combats churn with targeted Journeys campaigns >>
2. Get the timing right. When is the best time to ask people to upgrade? The answer is when it’s best for the customer. Usually, this happens toward the end of a series of trust-building messages, or based on user behavior, like product usage.
3. Use the power of loss aversion. Upgrade emails sent toward the end of a free trial are perfect examples of loss aversion in action. This is the perfect time to remind them of the value they’re getting—and what they’ll lose if they don’t upgrade.
4. Persuade with social proof. When someone else is vouching for your product, it builds a sense of authenticity. There are numerous ways to use this proof: testimonials, brand logos, badges from review sites, star ratings, and case studies.
5. Anticipate people’s needs. An effective upsell is time-appropriate based on the customer journey and behavioral data. Consider the signals that indicate someone would actually benefit from upgrading. That might mean they’re nearing the limit on certain features, incurring overage charges or growing their product usage.

Building your upsell email template is easier when you’ve had a peek at brands that have done it right. In these upselling examples, you’ll see a variety of successful approaches for connecting customers to the value of upgrading, expanding, and deepening their brand relationship.

SaaS graphic design platform for businesses and consumers

Why it works: Canva’s upsell email leverages a tactic familiar to anyone who’s used a freemium SaaS product: encouraging you to upgrade from a free to a paid plan. The messaging calls out what will be gained from upgrading. And they make the purchasing decision easier with a snapshot of their pricing plans right in the upsell email.

Online platform for train schedules and buying tickets across Europe

Why it works: Most of the time, when people buy a train ticket, they’ll need a return ticket too. Here, Trainline uses customer data (they haven’t booked a return ticket) to nudge the recipient to do something that’s genuinely helpful—save time at the station and ensure they have a seat.

Freemium SaaS online form builder

Why it works: This is a great example of a SaaS upgrade email using loss aversion to drive customers to action. You’re currently getting form views, but failure to upgrade might interrupt your service this month. A cool bit of psychology comes into play here: getting close to the view limit means the customer is succeeding, so upgrading unlocks more success!

B2B social listening SaaS platform

Why it works: In this example, Mention takes advantage of a new feature announcement to prompt people toward moving into a higher-tier plan. The messaging here is all about the benefits of the new LinkedIn keyword monitoring feature. Only at the end does the upgrade nudge come in.

Social media scheduling SaaS platform

Why it works: Like Mention, Buffer positions their upgrade email in the context of a feature announcement. For customers who already use Buffer to schedule posts on LinkedIn, the new feature amplifies the value they can get from the platform—and the upgrade CTA comes in after the reader has seen exactly how and why they’d want to try the new feature. The postscript on this upsell email is a nice touch: it offers another way people could leverage Buffer’s LinkedIn scheduling tools, even if they don’t upgrade to get the new feature.

SaaS landing page builder for paid ad campaigns

Why it works: Instapage brings another powerful psychological tactic to their upsell email: exclusivity. In addition to announcing new features available on an upgraded plan, they invite customers to get special early access to future updates. And there are no sales-ey “upgrade now” CTAs here—instead of asking customers to buy, Instapage encourages customers to try the new features. It’s a gentler way to ease people into an upgraded experience that will benefit them.

Accessibility and compliance SaaS platform

Why it works: Stark’s email does a great job of using stats to convey the value of an upgrade. All the above-the-fold content is laser-focused on the benefits of their premium plan. This is a great upselling example because it offers a compelling result—who wouldn’t want to be 10x faster and reduce issues by 50%?

Training, tracking, and networking platform for athletes

Why it works: Loss aversion is front and center in this upgrade email example from Strava. The recipient's free trial is over, and this message offers them the chance to get back what they’ve lost. By highlighting its most popular features, Strava reminds people of why they signed up for a trial in the first place.

Here at Customer.io, we take different approaches to upsell emails depending on a customer’s product use. Here is an example you can use as the basis for your own upsell strategy.

The approach: Our philosophy is that building mutually beneficial relationships is crucial to success—for our business as well as our customers. This upgrade template puts that into practice by offering an upsell at the exact time a customer has demonstrated that upgrading would be in their best interests. Here’s how we do it:

• Celebration: The customer is exceeding the limits of their current plan—and that means they’re growing! By congratulating them right off the bat, we reinforce that their Journeys use is producing the results they want.
• Personalization: We use customer data and dynamic content to reflect exactly what’s been happening with their billing in the last two months, so the email content is clearly relevant and timely.
• Value proposition: When people on our entry-level Essentials plan start spending more than the cost of the next-level tier, they’ll actually spend less and get more by upgrading—we specifically mention the most popular features of our Premium plan. This isn’t just an upsell; it’s a way we put our service philosophy into action.
• Service: Our CTA asks people to schedule a call with our upgrade team because they’ll be moving from self-service to a model with more customized options—and we’re here to help them align their particular needs and budget. Of course, if scheduling a call causes friction, we offer the option to email us instead.

By using elements like these for your upsell email template, you can create a customer experience that’s about solving their problems, not peddling your product. That’s the way to align your business objectives with your customers’ needs to build more trust and loyalty.

Your upsell emails can strengthen customer relationships, boost revenue, and improve customer experiences. Once you’ve nailed down acquisition and onboarding, it’s time to bring people further into the fold. Upselling emails live in the long lifestyle stage of retention—and when done well, they give people the added value that turns them into long-term loyalists.

Of course, ongoing experimentation is crucial for discovering the exact upselling techniques that drive conversion for your unique audience. To guide your test-and-learn strategy, grab our growth marketing playbook.