Product Recommendation Emails for Cross-Selling and Upselling

“Hey, you bought this. Maybe you’d like that!” But the truth? My emails flopped. Barely any clicks, let alone conversions.

Wanna know why?

Because I was sending the same generic recommendations to everyone—no personalization, no logic, and definitely no strategy. It wasn’t cross-selling. It was throwing spaghetti at the inbox.

Fast forward a few years (and a whole lot of A/B testing later), and I’ve learned how powerful product recommendation emails can be, when done right. If you’re in eCommerce or SaaS and want to boost revenue without hard-selling, this strategy’s for you.

Why Cross-Sell and Upsell Emails Work? (When You Nail the Timing)

Cross-sell and upsell emails aren’t just about making more money (though yeah, they do that). They’re about enhancing the customer experience.

When someone buys from you, they’ve already made a decision to trust you. That post-purchase window is gold—because they’re still paying attention.

Here’s the trick though: the recommendation has to make sense.

No one wants to buy a toaster and then get an email suggesting a bicycle.

Instead, think:

• Bought a phone? Recommend a case or screen protector.

• Subscribed to a SaaS tool? Offer a template pack or upgraded analytics.

• Ordered skincare? Suggest a bundle that includes the product they just bought.

The best cross-sell emails feel like a helpful suggestion, not a sales pitch.

The First Time I Got It Right

One of my clients sold planners and productivity tools. We added a simple automation: after someone bought a dated planner, they got an email three days later with a personalized bundle offer—stickers, pens, and a habit tracker.

Conversion rate? 18%. Just from a single email.

Even better? People replied saying, “This is exactly what I was looking for.” That’s when it clicked—smart recommendations aren’t annoying, they’re appreciated.

The Anatomy of a High-Converting Recommendation Email

Here’s what I include every time:

1. Clear Subject Line
   Something simple like: “You might also love these” or “Complete your setup.”

2. Relevant Product Recommendations
   Based on behavior, not just a random upsell. Use purchase history, browsing behavior, or even quiz results.

3. Social Proof
   Add a quick testimonial, review, or “bestseller” badge to boost trust.

4. Time-Sensitive Offer (Optional)
   Not always needed, but a “bundle discount valid for 48 hours” can give a gentle push.

5. Strong CTA
   One button. One click. Don’t make them think.

My Favorite Tools for Setting These Up

If you’re not doing this manually (please don’t), here are a few tools that make it easy:

• Klaviyo – Segment customers and automate based on past behavior. Works great for Shopify stores.

• ActiveCampaign – Smart automations, especially for SaaS.

• Mailchimp + Shopify – Basic but decent if you’re just getting started.

• ReConvert – Great for post-purchase upsell emails.

Pro tip: use dynamic blocks in your email templates. That way, each customer gets personalized product suggestions without you lifting a finger.

Common Mistakes I’ve Made (So You Don’t Have To)

• Sending too soon. Give people a minute to enjoy their first purchase before pitching more.

• Overdoing it. Stick to 2–3 product suggestions max. More than that? You’re overwhelming them.

• Forgetting the “why.” Always explain why a recommendation makes sense. “Pairs perfectly with…” goes a long way.

• Ignoring mobile. More than half of your users will open on a phone. Design accordingly.

Final Thoughts: Help First, Sell Second

Product recommendation emails are powerful not because they sell more but because they serve better. When you take the time to offer relevant, timely suggestions, customers feel like you get them. And when people feel seen, they buy.

So yeah, cross-sell and upsell emails are more than just marketing tricks—they’re relationship-builders. And with the right tools and timing, they can quietly become your highest-converting emails.