How to Upsell and make Customers even Happier…

Do you know what could really make a difference in a small business’s revenue? Upselling.

Upselling is when businesses try to convince their customers to buy an upgraded version of a product or service. For example, let’s say you go into a restaurant and ask for water. When the waiter lets you know it’s happy hour and drinks are half off, that’s upselling.

Upselling shouldn’t be confused with cross-selling, which is selling related items to shoppers. Both are valuable tactics but the approach can be different for each. Before we offer tips on how to upsell effectively, let’s look at how small businesses can benefit from it.

The Benefits of Incorporating Upselling into Your Marketing Strategy

Small businesses can benefit in several ways when they incorporate upselling into their marketing strategies. One of the main benefits is boosted revenue. Upselling prompts customers to spend more money with each purchase, which increases sales and a customer’s lifetime value.

Upselling is also good for product awareness. Instead of stopping at the product your customer purchased, you can bring additional products to their attention that will help elevate their experience.

Finally, customer retention improves with effective upselling. When you suggest an upgrade to your customers, and they have an exceptional experience with it, they’ll be more likely to become loyal, repeat customers.

How Small Businesses Can Practice Upselling Effectively

Small business owners approach upselling in various ways. What works for one business may not work for the next. But here are a handful of general best practices for upselling. 

Understand your target audience

First, you can’t effectively upsell to someone you don’t know and understand. In other words, identifying and marketing specifically to your target audience is critical to upselling.

You don’t want to approach every customer with a generic upsell offer. It won’t come across as authentic, nor will your customers be receptive to it. Instead, determine the upsell offers and marketing techniques most appealing to your unique audience.

It might also be a good idea to segment the pool you’re upselling to so that you can niche down your offers and how you present them based on things like what was purchased, their last marketing touchpoint, and genuine interests.

In addition to understanding your customers, you must also build trust with them for upselling to be successful.

Focus on building trust

Just because someone purchases from your business, it doesn’t mean they trust you. But trust is critical to effective upselling. This is because when someone trusts you, they trust your recommendations for how to make their experience better.

So, it’s essential to focus on building trust with your customers. One way to do this is through personalization. Every interaction a customer has with your business should be tailored to them. That way, they’ll feel like you genuinely know and care about them.

Collecting data on your customers through your marketing channels will fuel your personalization strategy. Just be sure you’re transparent about how you collect, use, and store customer data and how you will ensure their privacy.

Leverage multiple marketing channels

You’re probably already using multiple marketing channels to connect with potential customers and promote your products and services. If you aren’t, this is your sign to do so. You can use all or some of your marketing channels to upsell too.

Upselling doesn’t have to be limited solely to email marketing.

Start with an upsell email suggesting a valuable product or service upgrade for their recent purchase. Next, direct your customer to your website for more information on the upgrade. Then, share social proof with them featuring customers loving their original purchase with the upgrade. And finally, reach out to your customer via text or phone to continue the process.

Be sure to choose the best marketing channels for your target audience and strategize how to weave them together in your upselling strategy.

In addition to leveraging multiple marketing channels to upsell, it’s essential to perfect your copy.

Perfect your copy

Your words matter in your attempts to upsell. As you use multiple marketing channels, it’s essential to perfect your copy to ensure it prompts your customers to take action.

Determine the messaging and tone that would resonate best with your customers. Find keywords and phrases that make them want to do something. How can you guide your customers into their decision to purchase your upgrade rather than attempting to pressure them into it?

Be mindful of the words you use, how you structure sentences, and the visuals, layout, and links you use.

Make sure your upsells are worth it

A significant reason why upsells don’t work is that they aren’t worth it to the customer.

It’s vital to treat every customer as an individual and recommend things that make sense for them and the purchase they made. What upgrade can you offer to take their experience to the next level?

Your upsell should help your customer in some way. Be sure it’s a bargain too. Attach a discount to your upsell and make it a no-brainer value and price-wise.

Upsell after the initial purchase

Many small businesses decide to upsell while a customer is making their original purchase, whether that be while customers are browsing or directly on the checkout page. And this approach works for some. But for many others, it doesn’t.

Upselling after the initial purchase is a safer approach. You give the customer time to enjoy their initial purchase. Then, you take their customer experience up a notch by sharing a valuable upgrade available a week or so later.

Work on your after-purchase experience

If you’re looking to upsell after the initial purchase, you must work on your entire after-purchase experience. Some small-business owners don’t continue the customer experience after the purchase. Customers get a confirmation email, and that’s about it.

You don’t want to do the above, and the next time your customer hears from you is in an email where you’re trying to upsell them. It’ll turn your customers off and probably lead them to sever the relationship.

Your customer experience shouldn’t end with a purchase. Instead, it should evolve. Your customer should have an onboarding experience, showing them how to get the most from the product they just purchased and check-ins over the first week.

This ongoing communication with your customers will help them be more receptive to an upsell when that time comes.


Upselling is a smart business move. When done right, upselling can increase product awareness, improve customer retention efforts, and make your business more profitable. Use the suggestions above to ensure your upselling techniques produce positive results for your small business.

Jori Hamilton is an experienced writer residing in the Northwestern U.S. She covers a wide range of subjects but takes a particular interest in covering topics related to business productivity, marketing strategies, and HR solutions. To learn more about Jori, you can follow her on Twitter and LinkedIn.

Shawn Kinkade Kansas City Business Coach