10 Upsell Email Examples That Drive Conversions [+ Best Practices to Learn from Them]

Upsell emails are one of the most powerful tools in your SaaS growth playbook. When done right, they don’t just boost company revenue, but also help customers unlock more value and grow with your product. So, how do you write emails that convert instead of getting buried in the inbox? One smart way to learn is by analyzing upsell email examples from successful brands.

In this article, I’ve handpicked 10 upsell emails that would’ve worked on me, broken down what makes each one effective, and pulled out best practices you can apply to your own campaigns.

What does a good upsell email look like?

Before we dive into specific examples, let’s take a moment to break down the anatomy of a strong upsell email. Here are a few key elements that successful emails tend to have:

• A compelling subject line that hooks users: The subject line is the first and often only chance to grab users’ attention. So make it enticing, giving a clear hint at the value waiting inside. I also like adding personal touches, like the recipient’s name or mentioning a recent purchase.
• Strong value proposition statement: Good upsell emails answer the “What’s in it for my user?” They skip the technical jargon and focus on the benefits for the user, whether it’s saved time, improved collaboration, or an advanced use case.
• Product visuals: High-converting upsell emails embrace the show, don’t tell rule, embedding GIFs and videos that visually highlight how the upgrade delivers more value.
• Clear and actionable CTA: Converting emails contain CTAs that are impossible to miss, using contrasting colors and strong verbs. You should also be clear about what happens next, whether it’s starting a trial, scheduling a call, or upgrading with one click.
• Special offer (optional): And finally, converting emails often have a discount or a limited-time offer that creates urgency and encourages customers to act immediately.

10 Real-life upsell email examples from brands that got it right

Now, let’s have a look at some of my favorite upsell email examples and discuss why they work.

Upsell email example #1: Buffer

Social media scheduling platform Buffer uses the launch of its post commenting feature as a strategic moment to upsell users on basic plans.

What I like about this email:

• Conversational hook: They open with a trending question about the LinkedIn algorithm. This approach makes the email feel like a discussion with a colleague rather than a sales pitch.
• Embedded interactive demo: I find it cool that you can get a feel of the feature right in the email before and experience it directly in the email before committing to an upgrade.
• Value-add P.S. The email wraps with a LinkedIn engagement tip that ties directly to the new feature, encouraging deeper usage.

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Upsell email example #2: Zapier

Zapier sends this email to nudge free-tier users toward its paid Business plan by summarizing the value they got during the trial and the benefits they’ll lose if they don’t upgrade.

What I like about this email:

• Personalization: They pull in your exact task count (“You’ve automated 229 tasks”), so the email feels custom-made for you. Then, Zapier goes a step further by recommending the Business Plan based on your activity, helping reduce decision fatigue and guiding you toward the best-fit upgrade.
• Minimal design: A simple header, concise copy, and one bold “Select a Premium Plan” button keep the focus on action without clutter.
• Human touch: The email is personally signed by CEO Wade Foster and includes his photo, adding a layer of authenticity. It feels like a genuine recommendation from a real person, not just an automated prompt.

Upsell email example #3: Canva

Canva sends a product-led email to its free users, encouraging them to purchase the Pro version. What’s inciting is that it positions the upgrade not as a hard sell, but as an enhancement of what the user already enjoys.

What I like about this email:

• Conversational, playful tone that builds brand affinity: Light, witty phrasing like “Static designs are so 2017” keeps the email engaging and human without sounding pushy or overly salesy.
• Benefit-led framing: Sections like Animator (“turn static designs into animated GIFs or MP4s”) and Magic Resize (“instantly adapt your work for any format”) focus on tangible outcomes: saving time and making better designs.
• Bold visuals: High-quality images and layouts mirror Canva’s aesthetic, so you instantly picture your next design in Pro.

Upsell email example #4: Strava

Strava uses this email to nudge users whose subscription preview just ended to re-activate Premium.

What I like about this email:

• Copy taps into loss aversion to boost urgency: By highlighting that access to 30+ top features is now gone, the email leverages FOMO and makes the reactivation feel more compelling.
• Clean, modular layout that’s easy to scan: Concise benefit blurbs, eye-catching icons, and consistent “Explore” CTAs make the email visually engaging.
• Bold CTA: “Start My Subscription” uses first-person language to make the action feel user-initiated, while its bold design ensures it grabs attention instantly.

Upsell email example #5: Restream

Restream, a live-streaming distribution platform, sends this email in the final hours of a limited 20% discount on paid plans.

What I like about this email:

• Compelling offer: The 20% discount is stated upfront and bolded. There’s no ambiguity; users know exactly what they’re getting and why they should care.
• Countdown timer: The real-time countdown instantly grabs attention and drives urgency. It visually reinforces the message that the offer is limited, and time is ticking.
• Social proof: The “Trusted by” section with recognizable brand logos (Microsoft, Ubisoft, Cisco, etc.) adds authority and credibility, reinforcing the product’s value.

Upsell email example #6: Claude

Claude, Anthropic’s AI assistant, uses this email to introduce Claude 3.7 Sonnet (its newest hybrid reasoning model) and get users to upgrade to the Pro plan.

What I like about this email:

• Clear, informative subject and purpose: The email jumps right into the announcement; Claude 3.7 Sonnet is here. No fluff, no unnecessary intro. This directness respects the recipient’s time and aligns with a developer or tech-savvy reader’s expectations.
• Concise, benefit-focused copy: It does a good job of explaining the benefits of the Pro plan in coding, data analysis, and planning in just two sentences.
• Value-adding integration: Announcing GitHub support across all plans sweetens the deal and shows immediate ROI.

Upsell email example #7: Kickresume

Kickresume, the AI-driven resume builder, sends this email to encourage free users to purchase premium.

What I like about this email:

• Well-integrated social proof: Multiple user quotes, such as “Help my resumes stand out” from someone hired by Disney, and “Join 70,455 premium customers,” that build instant trust.
• Template showcase: Highlighting “50+ pixel-perfect, ATS-friendly templates” addresses the core need of standing out in applicant tracking systems.
• A risk-free CTA: “Get Premium from $4 per month,” paired with a money-back guarantee, helps readers overcome hesitation.
• Outcome-driven headline: “Go premium, get hired more easily” ties the premium membership to the reader’s ultimate goal: landing the job.

Upsell email example #8: Grammarly

Grammarly sends this personalized year-in-review email to free users, showing their total words written and mistakes corrected, then offers $100 off an annual Premium plan.

What I like about this email:

• Personalized usage recap: Displaying “74,044 words written” and “29 free mistakes corrected” gives users a sense of accomplishment and reinforces Grammarly’s impact.
• Good timing: A year-end summary can tap into users’ reflective mindset as they plan goals for the following year.
• Data-driven proof: Highlighting “12,286 advanced mistakes not corrected” shows the concrete impact Premium would have on your writing.
• Emotional touch: A congratulatory tone (“Nice job!”) warms you up before the upsell, making the offer feel like a next step in your progress.

Upsell email example #9: Veremark

Veremark, the background check platform, uses this email to nudge trial users to buy Credits before their free period expires.

What I like about this email:

• Urgency with a deadline: “You have only 3 days left on your free trial” to motivate the reader to act fast.
• Clear explanation of next steps: Laying out how credit bundles work and that larger bundles lower the cost per check removes any confusion.
• Data-driven benefits: Stating “complete background checks 33% faster” and “gain 60% more insight” gives solid reasons to upgrade.

Upsell email example #10: Freepik

Freepik, the go-to platform for stock photos, vectors, and design assets, sends this email to encourage free and monthly users to switch to its annual Premium plan at 40% off.

What I like about this email:

• Eye-catching hero design: A vibrant collage showcasing AI Suite previews and exclusive stock instantly demonstrates Premium’s creative power.
• Clear discount spotlight: The bold “40% OFF” overlay and an obvious “Get it” button focus attention on the deal.
• Quantified benefits: Points like “216,000 credits for AI tools,” “pause anytime,” and “priority support” make the upgrade’s value and flexibility clear.

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My best practices for designing upsell emails

Now we’ve looked at upsell email examples. Here are my tips for crafting the best ones that connect with potential customers at the right moment, address their individual needs, and drive your free-to-paid conversion strategy.

Segment your audience to send personalized emails

Email personalization goes beyond using the user’s name. It means crafting the content and flow based on clear user segments. Here’s how you can do it in Userpilot:

• Create segments based on user behavior, such as feature interactions, milestones reached, or past purchases.
• Group by job-to-be-done (JTBD). For example, product marketing managers track upsell email campaign metrics, or product managers monitor feature adoption.
• Create distinct email flows for each segment so that every customer receives personalized content. They should include triggers for the emails to send so users see the right upsell email at the right time.

Userpilot also allows you to create custom event triggers and conditions based on customer data inside your app. This way, you can refine your upsell strategy by tailoring delivery to send the right message at the right time.

Get the timing right

If you send upsell emails too soon, you may come across as pushy. Send them too late, and you can miss the moment.

I recommend you start by scheduling your emails.

Establish regular cadences, such as a 30-day trial check-in or a monthly feature roundup. In our tool’s engagement dashboard, you can schedule when to publish emails by the exact date and time.

Lead with the added value, not features

It’s tempting to list everything your premium plan includes: unlimited projects, advanced analytics, and priority support. But users don’t care about the features; rather, what they gain from those features.

Let’s illustrate this with an example. You are a product marketer using an email marketing tool. Think to yourself, which upsell message from the 2 below will prompt you to upgrade:

“Upgrade to Premium for unlimited projects and advanced analytics.

Or

“Unlock Premium to manage all your projects in one place and uncover growth insights in real time.

The answer is obvious. The second version doesn’t just describe capabilities, it promises outcomes, so that’s what would work on most data-driven professionals.

Include social proof

People trust other people more than brands. So when your existing customers see that others are achieving results from upgrading, it eases their doubts and increases the likelihood of upgrading.

Here are some ways I incorporate social proof into my emails:

• Showcase a brief customer quote that highlights the outcomes: Select a line where a user explains how the upgraded version addressed their pain point.
• Display recognizable client logos: Seeing familiar names can build credibility.
• Share key metrics for tangible proof: For example, “120 teams boosted productivity by 40%” grabs customers’ attention and helps them see tangible results.
• Embed short video testimonials: A quick clip of a happy customer

Consistently monitor email performance and improve

Don’t treat upsell emails as “set it and forget it.” The best emails come from constant measuring and optimizing based on what works best.

Here are some of the metrics I track and insights I gather:

• Delivery and open rates: Ensure that your emails reach inboxes and are opened by users.
• Click-through and click-to-open rates: Identify which CTAs resonate with readers and motivate them to take the next step. Whether that’s a purchase or registration.
• Conversion rates: Track the number of recipients who upgrade after clicking on a link.
• Unsubscribe rates: Flag fatigue or deliverability issues before they escalate.

Wonder how tracking these will help? Let’s have a look at a possible scenario. Let’s say your initial upsell email has a CTA like “Upgrade Now for 20% Off.” But you notice a 40% open rate but only a 4% click-to-open rate. You can A/B test a shorter CTA, such as “Get 20% Savings Now!” You may notice that clicks jump to 6.5%, which translates into a 12% increase in conversions.

Monitoring these metrics is a breeze with our dedicated email analytics dashboard. Besides viewing all the data in one place, you can also filter by segment, plan, or user behavior for granular analysis.

Supercharge your upselling strategy with Userpilot

Userpilot provides all the tools you need to launch and deliver effective upsell messages across different channels.

We offer a library of upsell emails that you can quickly customize with our no-code editor. Once the email is ready, you can configure targeting and set it to trigger based on real-time user behavior.

Want to see Userpilot in action? Book a demo with our team today and see how we can help you.

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