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11 Tips to Boost Your Revenue With Upsell Emails

Repeat customers are like the golden ticket to business success. They’re 50% more likely to try new products and, on average, spend 32% more. When you’ve got a fresh face as a customer, think of it as the start of something exciting. They’re just getting to know your offerings, and it’s your once-in-a-lifetime opportunity to build a relationship that keeps on giving. Your goal? Keep surprising them, always going the extra mile, and amp up the value you bring to their life in the long run.

Enter the scene: upsell emails, the trusty sidekicks in your marketing toolkit. They’re like your personal concierge, here to suggest the perfect solutions tailored to your customer needs, whether an upgrade, a little extra, or something that perfectly complements their previous purchase.

Are you ready to take your sales to the next level? If your answer is a resounding “Yes!” (and even if it’s a timid “Maybe”), you’re in the right place. In this blog post, we’re diving deep into the world of upsell email marketing and upsell emails and how they can turbocharge your sales.

The role of efficient upsell emails in driving more revenue 

Customer relationships are the lifeblood of your business. Happy, loyal customers buy more and bring in new business through referrals and reviews. 

Email marketing is like having a direct line to your customers, allowing you to share the latest products, sales, and updates with people on your email lists. Even better, these subscribers opt into these emails, making them more likely to convert.

Today’s email marketing isn’t about sending out generic messages. Instead, it’s all about slicing and dicing your list into segments and adding a personal touch to connect with your audience.

Now, you might think this all sounds like a lot of work, but here’s the cool part with emails: marketing automation and software do most of the heavy lifting for you. So, with a well-thought-out strategy, you can use that email audience to skilfully craft, customize, and build the perfect experience for your customers.

Email is like a trusty Swiss Army knife for marketers. It’s budget-friendly, can be easily automated, and consistently delivers the best bang for your buck in the marketing world. While cold email outreach platforms have value for achieving initial reach, upselling requires a different approach.

Let’s take a look at some tried and tested strategies that can take your email upselling game to the next level.

1. Divide your email audience into customer segments

Let’s start by organizing your email list into different segments. Not all your customers are the same and shouldn’t be treated as such. Segmentation allows you to send highly relevant and personalized content to each group. It’s like one-on-one conversation with each customer but without the massive workload.

Divide your users into segments based on factors such as:

  • Customer behavior: Are they active, regular, or just occasional shoppers?
  • Purchase history: What products or subscription plans have they bought before?
  • Demographics: Age, location, and other relevant data.

Email segmentation enables you to target upsell opportunities more effectively. You wouldn’t recommend a winter coat to someone living in a tropical paradise, right?

Imagine a B2B software company with clients worldwide. Your users are diverse — some are tech enthusiasts, while others are savvy business professionals. Naturally, they all come with their own distinct preferences and needs. How do you approach this varied crowd? You start by segmenting them based on their usage patterns, past interactions with your software, and their industry.

Extra reading: 8 B2B Marketing Automation Strategies or Tips to Keep Your Pipeline Full

To tech-savvy clients relying heavily on your software, you email them about the latest advanced features to enhance their experience. Meanwhile, for the businesses looking to expand, you offer an upsell to a premium version that can improve their operations. And for those users who’ve been quiet for a while, a friendly reminder with personalized tips to get the most out of your software is just the thing. 

Zapier sends a personalized upsell email to accounts with multiple team members:

Zapier upsell email for teams
Segment conditions in Encharge

2. Identify upsell opportunities for each segment

Now that your list is neatly segmented, it’s time to find the upsell opportunities. Consider what additional products, complementary items, or premium versions could enhance your customers’ experience.

Let’s say you work for a medical insurance provider, and you’ve gathered a fantastic list of customers thanks to your trusty medicare script. Now, what you want to do divide that audience into categories like “basic plan,” “mid-tier,” or “top tier.” This way, you can hone in on the perfect upsell prospects for each group.

To upsell effectively, it’s vital to understand customer needs. Demonstrate to your clients how the additional coverage you recommend fits their circumstances by giving scenarios where the extra protection would prove invaluable.

A marketing automation platform like Encharge allows you to create precise segments for your users using conditions like behavior events, email activity, company association, and more.

Encharge segment conditions interface
Segment conditions in Encharge

3. Craft attention-grabbing subject lines

Your upsell emails will only work their magic if they’re opened, right? That’s where the subject line comes in. A subject line should be like a trailer for a blockbuster movie — it needs to grab the reader’s attention and make them want to know more.

Get creative and playful with your subject lines. For example, consider a company providing cutting-edge software solutions for businesses. They’ve mastered the art of crafting attention-grabbing subject lines to boost email open rates:

This savvy business gets it: their emails are only as good as their open rates. So, they treat their subject lines like blockbuster movie trailers of the tech universe, carefully crafted to hook the recipients and make them super curious to see what’s tucked inside the email.

You can use an AI subject line generator to get inspiration.

Framer’s upsell email aims to convert free users to paid customers with a straightforward, attention-grabbing headline:

Framer upgrade email
Image sourced from

4. Create compelling email content 

Once your emails are opened, the content needs to dazzle your customers. Your upsell email template should be like a friendly chat with a real person, not a faceless corporation.

Here are some essentials to include in your upsell email template: 

  • Personalized subject lines and greetings: A personalized email greets the customer by name, setting the tone and initiating a friendly conversation. 
  • Showcase the recently purchased item: Introduce your email by first highlighting the item/s or subscriptions that your customer recently purchased. This catches their attention by showing that your email isn’t just a generic suggestion but a personalized message tailored just for them.
  • Present upsell products: Now that you’ve got their attention, it’s time to (hopefully) close the deal by presenting them with perfect upsell options. The success hinges on making sure your suggestions are relevant to what the customer bought before. This doesn’t just make them more likely to buy a complementary product but shows that you are paying attention to their needs and offering something of genuine value.  
  • Social sharing buttons: Include buttons and links for your recipients to share your product recommendations with their network. Don’t forget to include direct links to your own social media accounts to encourage them to follow your content.
  • Email preference options: Not every email will hit the mark. Give customers the option to update their buyer profile or adjust email frequency. You can also include a link for feedback, like downvoting a product they’re not interested in. Most email marketing tools offer a subscription preference center that allows this.
  • Provide contact information: Always include your business’s contact information in every email you send to customers, and avoid using no-reply email addresses.
  • Opt-out option: Nobody likes to see customers go, but they should have the choice. Your emails should make it easy for them to opt out whenever they want.

Trail guide and map hiking app AllTrails entices users to upgrade with its gorgeous presentation of their premium plan, impactful benefits, and clear footer:

5. Create urgency with time-limited deals or discounts

People love a good deal, and the fear of missing out is a potent motivator. Inject a sense of urgency into your emails by offering time-limited discounts or promotions. Let your customers know this amazing offer won’t last forever, and that they’d better act now to reap the benefits.

For example:

Restream countdown email
Image sourced from

6. Include a prominent, clear CTA button

Your Call to Action (CTA) is like a digital neon sign pointing your customers in the right direction. Make sure your CTA button is front and center so everything is clear about what you want the reader to do. Use persuasive language that tells them precisely what they’ll get when they click.

For example:

  • “Upgrade My [Product] Now and Save!”
  • “I Want the Best [Product] Experience – Upgrade Today!”
  • “Yes, I Want to Boost My [Product] – Take Me There!”

It’s hard to miss this CTA from bank holding company CapitalOne. The CTA would’ve been even more impactful if they included a benefit, like “Get your virtual card for a safer future”, but they have included them above the CTA, which compensates.

CapitalOne email with a good CTA
Image sourced from

7. Send upsell emails at strategic times

Timing is everything in upsell email marketing. Send your emails strategically when your customers are most likely to be receptive. 

For instance:

  • After a purchase: When a customer buys one product, that’s the perfect time to suggest relevant add-ons.
  • Milestone emails: Celebrate customer milestones like anniversaries or achievements with personalized upsell suggestions.
  • Post-purchase emails: Slip a gentle upsell nudge in confirmation emails, shipping notifications, or order updates. (Please remember that once you include a promotional message in your transactional emails, they are no longer considered transactional, and people should be able to unsubscribe from them).

Mac software company MacPaw offers a 30% discount for buying more of their products: 

MacPaw upsell email for new customers
Image sourced from

8. Employ email marketing automation

Managing individual emails can be daunting as your customer base grows. That’s where email marketing automation comes to the rescue. Automation allows you to schedule emails, trigger them based on customer actions, and keep the upsell process running smoothly. Automation is like having a dedicated assistant that never sleeps, always delivering the right message to the right customer at the right time.

Your Next Box product upsells
Image sourced from

Let’s take the example of a B2B software company. They’ve mastered the art of generating leads using content and run a successful blog where they regularly publish insightful articles and industry updates to keep their audience engaged.

Now, imagine you’re a potential customer speaking with one of their reps and interested in the software suite you’ve read about online. Following a successful sales call, their system springs into action. You receive a warm and appreciative automated follow-up email, along with a friendly nudge to schedule a personalized software demo.

Fast forward a few weeks post-purchase, and their trusty predictive auto dialer knows precisely when to ring you up for a chat when you’ve got a moment to spare.

Now, what is an auto dialer, you ask? It’s a handy tool that streamlines business by weeding out busy signals, voicemails, and disconnected lines. Instead, it automatically dials numbers from a list and connects you with real people when they pick up.

So, when you pick up the call, it’s that same friendly rep you chatted with earlier, just catching up to see how you’re liking the software. And guess what?  They’ve also got some exciting upsell opportunities for you. This could mean adding a robust analytics module or expanding your user licenses for a productivity boost. 

This call is swiftly followed by a tailored automated email with their latest offers, including tempting options to take their software to the next level. It’s like they’ve personalized these emails just for you, taking into account the specifics of your conversation. 

9. Utilize A/B testing to find the most effective approach

Don’t rely on guesswork; let data guide your strategy. A/B testing involves sending two versions of an email to a small portion of your list to see which one performs better. Test different subject lines, email templates, and CTA buttons to optimize your upsell email game.

Remember, what works for one segment may not work for another, so keep testing and refining your approach.

Spotify A/b test example
Image created by writer

10. Continuously monitor and analyze key metrics

Your upsell journey doesn’t end once the emails are sent. Keep an eye on key metrics such as open rates, click-through rates, conversion rates, and revenue generated from upsell emails. This data provides valuable insights into what’s working and what’s not.

Regularly analyze the results and adjust your strategy accordingly. Customer satisfaction, revenue, and lifetime value are the ultimate indicators of your upsell success.

11. Respond promptly to customer inquiries

You know, there might be times when customers have questions or uncertainties about your upsell offer. So, it’s crucial to be on the ball with customer service and get back to them quickly. A friendly and helpful response can make all the difference, turning a potential sale into a won opportunity.

Crafting a dynamic upsell email marketing approach

There you have it – a comprehensive guide on supercharging your sales with upsell email marketing. By harnessing the power of email, understanding your customer segments, and offering personalized, compelling upsell opportunities, you’re poised to revolutionize your sales strategy. It’s all about creating an email marketing approach that feels like a one-on-one conversation rather than a generic corporate pitch.

Ultimately, your upsell email marketing strategy should be a dynamic and evolving part of your business model. It’s your secret weapon to boost sales, increase customer lifetime value, and delight your customers with products or services that perfectly complement their needs. 

So, go ahead, personalize those emails, send them at just the right time, and watch your sales soar while your customers revel in an even better, more fulfilling experience. They’ll appreciate the thoughtful touch, and your business will thrive.

If you need help setting up your automated upsell emails, feel free to book a call with us. We have helped hundreds of product companies automate their email marketing, generating better engagement and more revenue.

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