When done right, upselling and cross-selling can feel less like a sales tactic and more like helpful guidance. Customers don’t mind spending more if what they’re buying solves a real problem or enhances their purchase. The challenge is knowing how to offer more without sounding pushy or transactional.
Let’s look at how retailers can approach upselling and cross-selling in a way that actually improves the customer journey—and drives revenue as a result.
Understand the Difference First
Upselling means encouraging customers to purchase a higher-end version of the product they’re considering. Cross-selling, on the other hand, is suggesting complementary products. If someone’s buying a laptop, upselling might mean guiding them to a model with more memory. Cross-selling could be offering a laptop case or software bundle.
Both techniques rely on timing, relevance, and a deep understanding of your customer’s needs.
Make Recommendations Contextual and Specific
Nothing turns customers off faster than generic pitches. When your upsell or cross-sell feels like a blanket suggestion, it’s clear you’re more interested in the sale than the customer’s outcome.
Instead, use data to personalize recommendations. If a customer is buying athletic shoes, suggesting moisture-wicking socks or a gym bag feels natural. It makes sense in the context of their purchase.
If you’re online, this could be done through automated logic tied to product pages. If you’re in-store, train staff to ask open-ended questions that lead to more thoughtful suggestions.
Train Staff to Focus on the Outcome, Not the Sale
Rather than encouraging staff to push higher-priced items, train them to focus on helping customers solve their problem more effectively. For example, if someone is buying a skincare product for dry skin, the staff might suggest a hydrating serum as an add-on—not to hit a quota, but to improve the results.
That subtle shift in intent changes the entire interaction. The customer feels helped, not sold to.
Use Language That Adds Value, Not Pressure
The way you phrase your upsell makes a big difference. Instead of “Would you like to add this too?” try “Most people who choose this product also find this helpful because…”
This frames your suggestion as advice, not an upsell. It also taps into social proof, which can ciate when you save them time and mental effort by curating a logical set of products.
Leverage Timing in the Buyer Journey
Upsells don’t always need to happen pre-purchase. Post-purchase emails are a great place to suggest items that complement what the customer just bought. For instance, “Now that you’ve ordered your running shoes, here are a few items to keep you going strong.”
You’re catching the customer in a happy state—they’ve already committed—and offering value without disrupting the original purchase decision.
Test What Works and What Doesn’t
Not every upsell strategy will land. It’s worth testing different placements, bundles, copy variations, and timing. Use A/B tests online or track staff conversion rates in-store.
Your data will tell you which tactics are adding value and which ones are annoying customers. Over time, this will help you refine your approach and find your sweet spot.
Use Advertising to Reinforce Smart Product Pairings
If you’re running paid campaigns, don’t just promote single products—test ads that highlight bundles or value-driven product pairings. A retailer using LinkedIn to target business buyers (e.g., for corporate gifts or branded apparel) could work with an expert familiar with LinkedIn ads best practices to structure campaigns that highlight product combinations or case studies of successful partnerships.
Pairing the right creative with customer pain points—such as gifting solutions that make HR or procurement teams look good—can dramatically improve ROI. And good targeting ensures the ads show up for decision-makers, not just general browsers.
Make It Easy to Say Yes—or Noincrease conversions.
Avoid hard closes. Phrases like “You’ll need this” or “You should get this too” can make people feel cornered. Let the decision stay in the customer’s hands.
Offer Bundles That Actually Make Sense
Bundles can be a smart way to increase order value, but only when they’re relevant. A tech retailer might bundle a gaming console with an extra controller and a popular game. A clothing brand might offer a styled outfit with a small discount when purchased together.
The goal is to make the buying decision easier, not harder. Customers appre
Good upsells don’t add friction. They’re easy to accept and just as easy to decline. Make sure your checkout process doesn’t feel like a gauntlet of extra offers. If customers feel like they’re constantly clicking “no thanks,” it chips away at trust.
Keep the experience smooth. Show relevant options, provide a clear benefit, and let them move forward quickly—whether they say yes or no.
Final Thought
Upselling and cross-selling are less about squeezing more dollars from each customer and more about enhancing their experience. When you understand what they need and offer suggestions with care, those “extras” become part of a solution—not an unwanted sales pitch.
If you’re using paid promotion to amplify your efforts, studying LinkedIn ads best practices or working with an expert can help ensure your upsell and cross-sell strategies extend beyond your website and into the awareness phase of your customer journey. Done well, it’s a win for both your customer and your bottom line.
