Hey it’s Chase and Jimmy here!

Growing your eCommerce business isn't just about bringing in more customers—it's about building lasting relationships that encourage repeat purchases. And no, that doesn’t mean spamming them with random offers.

Smart cross-selling and upselling can boost your AOV (Average Order Value) while actually making the shopping experience better. When done right, it feels helpful, not salesy. So today we're digging into our favorite upsell and cross-sell strategies to give your bottom line a boost.

Plus, keep reading for Chase's 10 high-converting copywriting frameworks and how this one outdoor brand is going all in on adventure in hopes to bring a new generation outdoors.

Let’s get to it!

🥱 The most boringly reliable Customer Support in email marketing.

No drama. No side quests. Just answers.

At Omnisend, they believe email marketing shouldn’t feel like an adventure. That’s why their Customer Support team makes your marketing journey as predictable as a trip to the vacuum cleaner store.

Because in the middle of a big campaign, you don’t need surprises. You need support you can count on.

Someone who’s so boringly reliable they even received actual awards for it.

It's true: Omnisend’s Customer Support team just won a Bronze and TWO Silver Stevie® Awards for excellence in Sales & Customer Service.

✅ 24/7 support—even on their free plan
✅ Award-winning service recognized for reliability
✅ No mystery, no chaos—just solutions

Omnisend. So good, it’s boring.

💡 Knowledge Drop of The Week:

Chase lives by this one copywriting rule: Never write copy from scratch, always use a framework.

He shared his 10 favorite frameworks for high-converting copy so you never have to stare at a blank page again!

💸 The Secret to Higher AOV: Cross-Selling and Upselling with Email & SMS

Growing your eCommerce business isn't just about bringing in more customers—it's about building lasting relationships that encourage repeat purchases. And no, that doesn’t mean spamming them with random offers. Smart cross-selling and upselling can boost your AOV (Average Order Value) while actually making the shopping experience better. When done right, it feels helpful, not salesy.

Let’s break it down:

Cross-Selling vs. Upselling: What’s the Difference?

Before we dive into tactics, let’s get clear on these two key strategies:

• Cross-Selling: Recommending complementary products. Think: adding a screen protector when someone buys a phone.

• Upselling: Encouraging customers to go for the premium version. Think: nudging them toward the latest iPhone instead of last year’s model.

Both strategies work—when executed properly. Here’s how to do it right.

How to Make It Work:

• Use Data Wisely – Identify which products are frequently bought together.

• Make It Seamless – Suggest add-ons naturally, not forcefully.

• Keep It Reasonable – Don’t upsell something that’s 2x the original price.

• Leverage Psychology – Convenience plays a big role; an easy add-on makes sense when someone is already buying.

• Use Benefit-Driven Messaging – Instead of "Upgrade to Pro!", say "Get 2x the battery life with Pro!"

Picking the Right Products to Cross-Sell or Upsell

Not every product makes sense for an upsell or cross-sell. The best pairings feel intuitive:

• Bundled Products: Sell a coffee machine? Offer a pack of coffee pods. One study found that bundled deals can increase conversions by up to 30%.

• Upgraded Versions: If a customer is eyeing a basic backpack, show them a premium one with extra features.

• Post-Purchase Add-Ons: Once they buy something, hit them with an accessory recommendation.

This product and refill bundle from Laneige is a spot on example:

Best Practices:

• Offer bundles with a small discount to increase perceived value. "Buy 2, Get 1 Free" works better than "10% Off."

• Use AI-driven recommendations to personalize offers based on browsing history.

• Test different combinations to see what converts best. Sometimes, a $5 add-on drives more conversions than a $50 upgrade.

• Showcase social proof. Add customer reviews of the suggested product directly in the upsell offer.

Automating Cross-Sells and Upsells Like a Pro

You don’t have to manually suggest products. Remember, automation is your friend. Here’s where smart triggers come in:

• Before checkout: Show suggested add-ons on the product page and in-cart.

• After checkout: Use post-purchase emails to suggest related products.

• Later on: Hit them with a well-timed SMS for a refill or upgrade.

This is how Caraway provides timely offers at checkout with their “Complete your kitchen” recommendations:

Best practices:

• Set up email flows that suggest add-ons based on purchase history.

• Use SMS for fast, high-converting upsell offers. Open rates are 98%—way higher than email.

• Create urgency. "Only 5 left!" or "Exclusive deal for the next 24 hours."

• Test placement. Amazon does a great job with "Customers Also Bought" right before checkout.

Example Flow:

1. Customer buys sneakers → Post-purchase email suggests matching socks

2. One week later → Follow-up email offers a premium shoe cleaner

3. One month later → SMS reminder for a new pair of laces or a protective spray

Evergreen vs. Time-Sensitive Offers

Some upsells should always be running in the background, while others work best as limited-time promos.

• Evergreen: Recommendations in welcome flows, transactional emails, and post-purchase messages.

• Time-Sensitive: Flash sales, exclusive bundles, or limited stock warnings.

Bubbles “Build your routine” email is great evergreen content that fits perfectly into a welcome flow or could easily work into a post-puchase flow with a “Complete your routine” spin. 

Best practices:

• Regularly update your automated sequences with fresh offers.

• Use countdown timers in emails and SMS to create urgency.

• A/B test different approaches to see what works best.

• Leverage FOMO. "50 people bought this today!" can nudge hesitant buyers.

How to Measure Success (And Fix What’s Not Working)

You can’t improve what you don’t track. Key metrics to watch:

• AOV: Is it actually increasing?

• Attach Rate: How many people take the upsell offer? If only 1% do, you might need a better pairing or incentive.

• Conversion Rate: Are these recommendations leading to actual sales?

Optimization Tips:

• A/B test different product pairings and messaging.

• Check unsubscribe rates. Too many aggressive upsells can backfire.

• Ask customers for feedback on recommendations (simple post-purchase survey works great).

• Use heatmaps to see if people engage with your upsell offers before abandoning cart.

Common Mistakes to Avoid

Cross-selling and upselling should feel natural—not forced. Here’s what NOT to do:

• Overloading customers with too many suggestions at once. Limit upsell attempts to 1-2 per session or email.

• Recommending irrelevant products (don’t suggest dog food to someone who just bought a cat bed). Personalize recommendations using real customer data.

• Hiding costs. Be upfront about pricing and benefits. Focus on VALUE. Explain why the suggested item improves their purchase.

• Forgetting about timing. An upsell at checkout is smart, but pushing another big purchase 24 hours later can feel pushy.

When done right, cross-selling and upselling aren’t just revenue boosters—they actually make the shopping experience better. Customers get relevant, helpful recommendations, and you get a bigger AOV. Win-win.

Now go make that extra revenue happen!

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Answer these five critical questions:

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4. How much time does your finance team spend on tax compliance tasks?

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🔥 DTC wins:

After facing declining sales, Teva goes all in on adventure with their new campaign, "For Playground Earth." The spring/summer collection blends archival and new styles, spotlighted by real outdoor enthusiasts trekking through epic landscapes.

It’s not just about selling sandals—it’s about selling the adventure they take you on. Smart move for a legacy brand trying to keep its DTC game strong.

Annnnd that’s a wrap for this edition! 

Thanks for hanging with Chase and me—always a pleasure to have you here.

If you found this newsletter helpful (or even just a little fun), don’t keep it to yourself! Share ecomemailmarketer.com with your favorite DTC marketer. Let’s get them on board so they don’t miss next week’s drops.

Remember: Do shit you love.

🤘 Jimmy Kim & Chase Dimond

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