How to increase sales online by authentically upselling

7 min read
Ashliegh Gehl

Upselling is a strategic tactic that gently encourages the consumer to build upon their original purchase. If done well, it can increase sales while enhancing the customer’s experience, strengthening brand loyalty and fostering a community.

One of the most common upselling examples is the experience we’ve all had at restaurants. Upselling is an integral part of the restaurant culture. You might find yourself ordering items you never even thought you’d consider. The server’s mouth-watering description of scallops has you hankering for a plate before you even review the menu.

Remember, the server knows you’re there to eat. What you decide to eat can be swayed by strategic upselling.

Our response to upselling depends on three factors: Appetite, timing and curiosity.

3 ways to sell more

Increasing the order size of those who are already buying from you is a tried-and-true method of increasing revenue. Here a few of the most popular tactics.

  1. Make related recommendations.

  2. Tell stories.

  3. Target your offers.

Before we delve into our strategies, including upselling examples, let’s talk about the factors that affect how receptive your customer will be to a ‘buy more’ offer.


There’s a reason the adage ‘don’t shop on an empty stomach’ rings true. You’re likely to purchase more food when you’re hungry. And if you’re hungry enough, you’ll order appetizers simply because you’ve overestimated just how hungry you are.

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Restaurant staff are masters at upselling, getting diners to order things they didn’t intend to.
Photo: Vladimir Kudinov on Unsplash

Needless to say, the same holds true for people who are shopping for goods and services. In this case, appetite might be triggered more by economic factors than physical ones. While you can’t control this factor, you can be ready with an offer if the customer happens to be ready to buy.


Knowing when to upsell, with the intent to increase sales, is just as important as the offer itself. The server isn’t going to recommend scallops at 9 a.m. when the customer is ordering breakfast. That mouth-watering description quickly becomes unappetizing. That’s why it’s all about timing.

Timing is just as important for a product or service provider.

Retailers, for example, often feature seasonal products in their displays — both in-store and online — because they know people are actively looking for those products.

Another example might be the common practice among residential contractors of approaching people who’ve just purchased homes, since they're likely interested in kitchen or bathroom upgrades.


If you’re a regular at the restaurant, the server might know that your culinary tastes are fluid — that you’re up for new and exciting suggestions. Or, that you’re consistent: You always order beef and potatoes. But what kind of beef? Porterhouse? Filet Mignon? New York Strip?

A good server builds a relationship with returning customers and tailors suggestions to the guest’s interests without focusing on price. The upsell is focused on creating an enjoyable dining experience that is memorable.

The best upsells are personal.

Depending on the type of business you have, be it a brick-and-mortar store or an eShop, upselling tactics will differ. It isn’t a one-size-fits-all approach, especially for locally-owned businesses dedicated to building long-lasting relationships with their customers.

Pro tip: The No. 1 mistake companies make when upselling is underestimating the shopper’s awareness of what they’re up to.

Consumers know when they’re being targeted. If your upselling methods lack authenticity, your customer might not buy what they originally came to purchase. Or, if the approach is too aggressive, they could shy away from your business altogether and shop online with a competitor.

Upselling done right

Here are three upselling techniques that will enhance the relationship you have with your customers while increasing sales and building loyalty. We’ve included upselling examples to illustrate each one.

Being a reliable source of information puts business owners and their passionate staff in a position to provide recommendations.

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Amazon increases sales by suggesting products related to the customer’s choice.

An example of this is a clothing store that carries both brand name and no-name items. If the customer is shopping for a black dress, don’t recommend the priciest item in the store. Choose a variety, with different price points, and casually share your knowledge about them.

The dress that is $50 more might be wrinkle-free, a feature that could be appealing. Let the customer decide. And once the customer is happy, you can build upon the upsell by cross-selling. Does the customer also need:

  • Tights or nylons?
  • Heels or flats?
  • Costume jewelry or diamonds?

Every layer is helping your customer reach the look they’re trying to achieve.

2. Tell stories

Sometimes the upsell has more to do with the story and less to do with what you’re actually selling.

When it comes to buying insurance, there’s always a reluctance to pay more for additional coverage. A new homeowner could think, ‘It’ll never happen to me.’ It’s a common thought that holds some weight. The worst-case scenario might never happen to them, but this is where the power of story comes into play.

Share stories and details about what you sell.

As the seller of insurance, you know it’s not enough to have a basic plan. Perhaps the area where the homeowners purchased is prone to flooding. Or it’s located in tornado alley. You know what has happened to people who live there and you know what’s possible.

By sharing these stories with your clients, you’re informing them of the risks. The intentions of the upsell are in the best interest of your client because you sincerely wish that they never find themselves in a compromising position.

3. Target your offers

Imagine you’re online shopping for flowers. It’s a friend’s birthday and you forgot to send a gift. The website knows the flowers are for someone’s birthday, because you selected the flowers from the birthday category.

Increase Sales Umbrellas
A client shopping for bikinis might not be interested in an upsell offer for umbrellas.
Photo: A. Zuhri on Unsplash

As you navigate the payment process, you receive a prompt to upgrade your order. An additional 12 roses will only cost $10 more. The arrangement will double in size. The florist knows that flowers don’t last forever. By offering more, and charging less, the florist is able to increase the sale.

Another way to enhance this sale is through offers for:

  • A birthday card
  • Balloons
  • Teddy bears
  • Chocolates

By automatically bundling these items, the customer is put in a position to consider whether or not they wish to enrich their gift.

Targeted advertisements can also save sales. Let’s say you made your way to the end of your flower purchase, but decided at the last minute that you really don’t have the money for it. The moment you leave the website to check Facebook, you’re served ads reflective of your potential purchase. A reminder email is waiting for you in your inbox.

Reminders like these can encourage your customer to return to complete their purchase. This is called retargeting because you’re bringing them back to a product they’ve already expressed an interest in.

Editor’s note: Online Store from GoDaddy automatically emails shoppers who leave before checkout, reminding them to complete their purchases. This increases sales for Online Store owners.

Win-win: Increase sales and build loyalty

Upselling is the art of taking a purchase to the next level. It’s threaded through every successful sales strategy. Sales staff are encouraged to be mindful of their attitudes and their approach. A hard upsell can turn customers away.

Make the buying experience personal by offering related recommendations and by telling meaningful stories the customer can relate to.

There could be a sales quota you want to achieve for the week and an ultimate business goal to increase sales, but the client should never feel as if they’re being pressured to consume in order to meet your target. At the end of the day, a loyal customer base is what matters.