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April 26, 2017
E-commerce  |  7 min read

5 Ways Automation Helps you Supercharge Cross-Sells and Upsells

As a small business owner, you know that running a business is a creative venture. It requires innovation and experimentation—and continually dreaming up new ways to delight your customers. The good news is that with today’s smart tools, you can grow your e-commerce small business in incredibly sustainable ways. How? By bringing intelligence into your sales platform and turning your website itself into a genius salesperson.

An impressive 45 percent of small businesses expect to grow more than 25 percent in 2017—and many of them will be doing this via the fine art of cross-selling and upselling. We spoke with several business mavericks about how they are boosting cross-selling and upselling into the online shopping experience, and seeing real results:

But first, some definitions

Upselling is when you’re suggesting your customer increase their purchase by either adding additional items or shifting to a more premium version of their original choice—think of the classic McDonald’s line, “Would you like to supersize that?”

Cross-selling is its close cousin where you suggest related products that will go supremely well with the original purchase. For instance, if you’ve just added a sleeping bag to your online shopping cart, there’s a good chance you might also like a padded mat—and maybe even a tent. Amazon mastered the art of cross-selling with the “Customers Who Bought This Item Also Bought” window; in 2013, the goliath attributed 35 percent of its revenue to this form of cross-selling.

When done well, it’s a process that delights both the customer and the entrepreneur: you’re able to predict their needs without them having to ask, while generating more revenue from the purchase. But how can you start to automate these two income-boosting steps into the buyer journey?

1. Offer pricing incentives for leveling up 

Drew Sanocki, former CMO of, writes a compelling blog on BigCommerce about the power of cross-selling and upselling and its massive potential boosts to the bottom line. He explains savvy ways to use discounts to incentivize bigger purchases: On the BigCommerce platform, for example, customers can be incentivized all the way from the product to the checkout page, with offers such as "Free Shipping on orders over $100."

You can create a variety of packages to entice people to increase their order value with cross-selling options or opt for a more expensive version of the product. These suggestions, built into various pages along the buying journey, act like your digital sales assistant, bargaining with the customer—and luring them into a good deal.

2. Do the thinking for the customer

Put yourself in the buyer’s mind when deciding what to recommend. Cross-selling works best when it makes complete sense to the buyer. Robert Garcia runs the e-commerce site, and he says he was taking a run-of-the-mill approach to cross-selling until it dawned on him that he was missing a crucial opportunity. He wasn’t answering the potential pain points for the customer, fine-tuning recommendations that were intelligent and useful. He realized he needed to turn cross-selling into part of the discovery process itself.

“We were leaving too much money on the table,” he explains. “And customers were getting frustrated that they were not getting the benefit of the product availability on our site.” He started to think about what the customer would need alongside that specific umbrella. This meant both upselling and bundling together ancillary accessories that buyers wouldn’t realize they would need until actually unpacking the umbrella on their patio. These recommendations increased the company’s average order value by up to 50 percent. “Your customer is so focused on what they want, that they forget to ask what they need,” says Garcia.

3. Throw in freebies  

Paul Jarrett is the co-founder and CEO of Bulu Box, an e-commerce business built upon the gold of bundling products together. Bulu Box sells boxes of health supplements, allowing people to try out a variety of bite-sized samples all in one go. Jarrett says that offering a gift with a product proved to be a powerful tool to increase sales. “Sales of a $24.99 low calorie, sugar-free protein increased 30 percent during a promotion where the customer received their choice of a thermogenic pill or cleanse and detox product as a gift with purchase,” he explains. “We have combined this with an upsell—don't buy one of this product, buy two boxes and get a free gift. If the margins make sense, it can bring in high revenue and profit.”

4. Offer premium service upsells

What can you offer that’s more valuable than any product in your shop? Your own time. You, after all, are the expert, and your customers are likely to bite at an opportunity for a 1-on-1 consultation with you.

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Consider an example cited by Sinocki: A friend who ran a framing shop was looking for ways to expand revenue, but most customers wouldn’t spend more than a few hundred dollars at a time. He helped her develop a custom upsell to customers who were already buying framing services: A personalized art advisory service, in which she’d hold Skype consultations to review the customers’ style and provide customized artwork recommendations, for $1,000 each. Not all customers bought into the service, but many did.

This is the creative part of the business-building process, an ability to dream up new services and provide solutions to the pain points of your customers. Is there a related service you too could dream up?

5. Reach back out  

Finally, your upselling and cross-selling shouldn’t end the moment the customer leaves your site. Howie Zisser spends his days helping e-commerce fashion clients with the Chicago-based digital marketing agency Matchnode. His recommendation is to analyze your customer segments’ order sizes and frequency, looking back over historical data to understand your most valuable customers and what their average order size is. Then be strategic in touching base with them.

“Say they typically reorder every eight months,” says Zisser. “We will begin specifically retargeting this cohort about five months after their last purchase.” He says this brings two key benefits: reorder rates are shortened, and you can provide offerings based on their purchasing history. Zisser also emphasizes the need to have an “abandoned cart” reorder campaign automated into your site for all those souls who get distracted away. “These people are literally telling you what they're interested in, so a well-crafted retargeting campaign featuring that specific product can be very effective,” he says.  

By plotting some of these strategies into the buyer journey on your site, you will begin to tap into a bigger pool of potential sales. Focus on delivering natural offers, that feed organically into what your customers are likely to be interested in—and optimize your timing to catch your prospects when they’re most primed to make a purchase. By making these steps automated, using intelligent online tools that do the work for you, you’ll be allowing more sales opportunities to flow into the daily running of the business.

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