If you’re planning to ask your subscribers to purchase more from you through upselling, make it worth their while.
When used strategically in promotional messages or follow-up messages, upselling builds trust, increases satisfaction, and naturally increases revenue.
One of the most effective channels for this is email, especially if your campaigns are timed correctly and individualized to the customer's behavior.
Take a look at these 10 upsell email examples to understand what works, when to use them, and how to customize them for greatest impact.
What is An Upsell Email?
Upsell emails are marketing emails suitable for pitching shoppers your more premium product or service.
These emails are designed to invite customers to get more out of (and pay more for) what you offer. In essence, you’re deepening the relationship—or, for subscription-based businesses, prolonging it.
In addition to boosting customer lifetime value, this strategy also increases average order value. Upgrades add directly to your bottom line. They’re a simple way to maximize profits on every sale.
However, upselling isn’t the only way to strengthen your connection with current customers and keep them coming back for more. Cross-selling is another one, although this approach works differently.
In the next section, you'll discover where they differ, so you can use both effectively.
Upsell vs. Cross-Sell: What’s the Real Difference?
Chase Dimmond, a renowned email marketer, bundles upsell and cross-sell in his list of “8 types of emails brands need to send”. Basically, both “use purchase history and customer preferences to personalize these (product) suggestions.”
That’s absolutely true, but here’s where they differ:
- Upsell offers a better version of what your customers previously purchased or are planning to. Cross-sell offers related products that go hand-in-hand with the product they just bought or are looking forward to.
- Upsells tend to raise the overall quality or spend per item. Cross-sells often increase the total number of items in the cart.
- Upselling leans into “go bigger.” Cross-selling leans into “don’t forget this too.”
If you’re still not sure what upsell emails look like, that’s about to change. Below you’ll see real-life examples that show you what it's all about.
10 Smart Ways to Use Upsell Emails (with Examples to Steal)
These 10 brands brilliantly demonstrate how you can turn a simple email into a winning pitch:
1. Pendleton Whisky’s New Product Intro
I can’t blame you for wanting to show off your new product. It’s the result of your months of hard work and dedication after all. The good news is that this is what an upsell email is for. Look at this ecommerce upsell email example from Pendleton Whisky:
Source: Email Love
What you can borrow:
- The limited edition bundle strategy. Give your shoppers an incentive to make the purchase. If it’s not a limited edition, try offering free shipping, early access, or a small bonus product to sweeten the deal and make the upsell feel like an easy choice.
- Strategic CTA position. Pendleton Whisky strategically places the same call-to-action button three times: after introducing the product, after listing its features, and again after the bundle offer. Doing so reinforces the single action you want your reader to take: get them closer to checkout.
2. Linktree’s Upgrade Freebie
Upsells don’t only work for ecommerce brands. A generous incentive can give users more reason to click upgrade, no matter your industry. Linktree, a link-in-bio SaaS platform, encourages them with a free 30-day off when you upgrade to “Pro.” Check out this SaaS upsell email example:
Source: Really Good Emails
What you can borrow:
- Gift psychology. They designed the email like they’re giving you a present. The subject line, “Try Linktree Pro on us,” paired with an exclusive code, can make users feel like a personal reward has been given to them. This messaging can make recipients feel valued, not marketed to.
3. Frontman’s Best Sellers
Entice your customers to shop more with you by showing them what other people are getting. FOMO always works, especially on younger shoppers.
Plus, bestsellers make a strong case for their value. If other people are using them, then they must be worth the purchase. Use this technique to gain customer trust and remove decision fatigue.
This upsell email example by Frontman demonstrates one of the most clever ways to highlight your bestsellers:
Source: Really Good Emails
What you can borrow:
- Social stats. Instead of just saying “most popular,” Frontman throws in a real figure: 10,000+ men have used these anti-pimple products. Someone suffering from acne will be easily persuaded by this level of social proof. The more specific you can be, the better. But never exaggerate. Most modern shoppers are discerning, and they’ll see right through anything that doesn't feel right.
- Credible endorsements. In the subject line, Frontman mentions that GQ and Esquire love these products. If trusted publications or organizations recognize what your product or service does, you get instant authority and buyer confidence. The only thing I’d suggest to really sell this positioning is to bring it into the email body, too. Frontman could have easily added a seal from those publications or a quote blurb to support the claim.
4. Restream’s Upgrade Discount
Discounts are always welcome, especially when you’re encouraging customers to upgrade. Restream has the right idea, urging their customers to act on this upsell email offer.
Source: Really Good Emails
What you can borrow:
- The urgency element. Put the squeeze on your shoppers and get them to act now. Without a deadline, even interested customers will postpone decisions. Plus, you can't keep your prices low for a long time, because that could make your product or service seem less premium. Limiting its availability does the opposite, though, because scarcity can signal importance.
- Flexible offer. Restream doesn’t lock the discount to a specific plan, as it applies to any streaming plan of the user’s choice. This kind of flexibility gives people the freedom to choose what works for them. You can borrow this strategy, even when you’re in retail. For example, try offering discounts across categories or bundles rather than just select items.
5. Athletic Greens’ Subscription Invitation
Subscription upgrades aren’t just for SaaS brands. Athletic Greens provides a great example of how an upsell email can turn one-time buyers into longer-term customers through a quick and well-positioned offer.
Source: Really Good Emails
What you can borrow:
- A quick rundown of what's in store. Athletic Greens mentions what’s in it for the shopper when they sign up for a subscription plan. This is a great move. When you’re asking customers to commit to recurring purchases, you’re asking them to invest more in your brand. Explaining the added value (in Athletic Greens’ case, $20 monthly savings, exclusive access, and a welcome freebie) helps justify that leap.
- A short testimonial. When upselling, why not throw in a customer quote to back it up? As mentioned earlier, people love hearing what others think. It doesn’t have to be much. A single, short testimonial can convince them that the upgrade is worth the extra dollars in the long run.
6. Hanni’s Seasonal Offers
As the seasons change, assist your customers in their shopping journey by showcasing your season-appropriate product recommendations. Seasonal upsell emails help you tap into buyer mindset shifts. In this way, you can satisfy current needs and stay relevant in their inbox.
Take it from Hanni. This summer-essential upsell email example has plenty of takeaways to copy:
Source: Really Good Emails
What you can borrow:
- Excellent imagery. Hanni uses both a lifestyle shot and a product-in-use photo, which is especially effective for seasonal upsells. These images are likely to tempt shoppers to treat themselves to this upgrade because they help shoppers visualize the product in their current context. Sometimes that’s all it takes to make an interested audience convert.
- Cross-sell opportunity. Okay, okay, this isn’t about upselling—but if you have a chance to increase order value, take it. Hanni sneaks in a small cross-sell near the end of the email, featuring their shower scarf. It doesn’t steal focus from the hero product. In fact, it complements it.
7. Graza’s Replenishment Reminder
Replenishment reminders are essential—they keep your product top-of-mind just when the customer needs more. But they’re also perfect upsell opportunities. Here's how Graza does it:
Source: Really Good Emails
What you can borrow:
- Simple, clear messaging. Graza is banking on their customers’ first positive experience with their olive oil. And they’re right to. If customers loved it, they're likely to reorder. Instead of having to go over to your website to make a purchase, they can do it immediately upon reading the email. That’s how upsell emails should feel: easy, natural, and frictionless.
8. Mr. Porter’s Product Suggestions
Why not put your favorite products—I’m sure you and your team have some—front and center? Including top picks makes your email feel like a friendly recommendation. That’s exactly what Mr Porter, a luxury fashion marketplace, nails in this upsell email.
Source: Really Good Emails
What you can borrow:
- Personalized curation. Product recommendations should feel like advice. These picks come from a named editor at Mr Porter, giving the email a sense of care and expertise. Readers feel like they’re being let in on insider favorites, which builds trust and adds a soft-sell emotional layer.
9. DocuSign’s Free Trial Over
Has your customer’s free trial come to an end? You might want to give them a nudge. This simple upsell email example from DocuSign proves you don’t need fancy designs or lengthy copy to make the message clear.
What you can borrow:
- Shortness and succinctness. DocuSign uses barely 50 words, yet the message lands: If your customers liked their experience with the platform, they can check out what plan suits them best. My favorite part is how they frame the next step—”view plans”—which feels light and approachable. They’re simply asking their customers to explore more. No one’s asking them to open their wallets just yet.
10. LinkedIn’s Hit Your Limits
If your user has already taken advantage of their free credits, it’s the perfect time to offer an upsell. You've already proven the product works. So, offering more of what they already use is just something natural (and helpful). LinkedIn uses this strategy by highlighting a pain point. Here’s the upsell email example:
What you can borrow:
- An explanation of the limit. If you’re offering usage caps like LinkedIn, which is a free social media platform, explaining why those limits exist can reduce frustration and build trust. In this case, search restrictions are in place to ensure a quality experience for all LinkedIn users.
- Feature highlights. LinkedIn mentions a key upgrade: advanced search, which lets users filter by company, title, and more. This quickly shows what paying makes possible. A single well-placed feature based on what your user needs is more convincing than a long list.
- Free offer. Just because the free tier has limits doesn’t mean your upsell has to be hard-edged. Depending on your business model, try softening the message, like LinkedIn did. They offer a free one-month trial of Premium, lowering the barrier to entry.
When to Send Upsell Emails
You’ve nailed the messaging and approach. The other thing you should consider when sending upsell emails is timing. The right moment makes your offer feel helpful, not salesy.
Find strategic moments to send your next one using the timing suggestions below:
- Right After Purchase: It’s easier to get another “yes” when they’ve just given it to you. Customers are already in buying mode, so take advantage while their interests are still high.
- Pre-Renewal or Upgrade Point: Get your customers' attention before renewal to remind them of the better features your premium tiers offer. Done right, you can lock them in before they reconsider.
- When Product Use Peaks: If your customer is (constantly) hitting limits or showing high engagement, it's a signal that they're ready for more of what you offer. Offering an upgrade feels like a helpful assist here, since they already recognize the need themselves.
- Seasonal or Special Events or Milestones: Events like holidays, birthdays, or even brand anniversaries are perfect opportunities to offer limited-time premium upgrades (bonus if you throw in discounts or freebies).
Upsell, Upsell, and Profit Away
It's easy to set up well-timed upsell emails, and they're incredibly effective at turning one-time buyers into loyal, higher-value customers. Don’t be afraid to experiment and A/B test to see what resonates best with your audience.
If automating campaigns feels overwhelming, don’t fret. Here are some solid guides for leveling up your automation game so your upsell (and cross-sell) emails always land at the perfect moment.
- Email Automation Software: What’s The Best Choice For Your Business?
- Ecommerce Marketing Automation Guide: Get Started in 5 Step
- Marketing Automation Strategy: Getting it Right in 6 Steps
- Automated Email Examples: 13 Quick-Win Ideas for Boosting Engagement
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