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How To Upsell Any Customer

BY: Nguyen-Ngoan  |   July 31, 2018
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Upselling is the lifeblood of many business models. Some companies are even willing to sell some items or services at a loss, banking on the hope of a future upsell.

As a leader of several SaaS companies, I’ve discovered through trial and error some techniques that will guarantee upsells. Every business is different, and every customer is unique, but these tactics are sure to generate more upsells for your business.

First off, what is upselling? Upselling is getting your customer to make a higher cost purchase than he or she originally planned.

The goal is compounding profit by using the momentum of purchase. My model in upselling is to earn 30% or more of the business’s profit from upsells. Since upselling current customers is 5-10 times cheaper than acquiring new ones, it makes pure business sense. Build upsells into your business from the very beginning, and design your marketing approach around an upsell strategy.

1. Make the upsell relevant to the customer’s original purchase.

If you’ve ever ordered at a McDonald’s, the cashier may have asked you, “Do you want fries with that?” Fries go with burgers. Their upsell is relevant to your original purchase.

Bluehost does the same thing with their hosting. They throw in a lot of upsell pitches, but they are all generally related — extended hosting, domain security, additional domain endings, etc.

Relevance is the key to successful upselling. A customer becomes a customer by buying one product. Make sure that you either augment or improve that product with your upsell.

Here are some examples:

  • You sell a knife. Sell a knife sharpener.
  • You sell software. Sell premium support.
  • You sell sunglasses. Sell a microfiber cleaning cloth.

2. Make your customers sell themselves.

One of the best SaaS upsellers is Salesforce. Here’s how they do it: storage limits.

Built-in limitations are a brilliant upsell for SaaS providers whose process includes storage or bandwidth. If a user wants more data or more storage, they have to pay for it.

By using this approach, you aren’t making a huge or obvious effort to upsell them. The customers themselves realize the need and make the prudent decision to upsell.

Joel York calls this “design for discovery,” and explains,

Your customer naturally discovers and digests new capabilities just-in-time as its needs grow.

The most successful and complaint-free upsells are those in which the customer realizes his or her own need and makes a willing purchase.

3. Make your upsell discounted.

Customers can smell an upsell. They are going to think about the upsell from one main perspective: How much does it cost?

If your upsell is too expensive, they won’t bite. If, however, it’s a discounted upsell, they will be more interested.

Here’s a rule of thumb: The upsell should be half the cost of the original purchase (or less). The customer is trying to rationalize the price. They’ll think, “Well, I’m already buying this, which costs $100. I might as well buy this, too. What’s another $50 anyway?”

If you want to make a higher upsell, be sure to break it down into a payment plan — e.g., only $29/month for six months — to create the illusion of a lower price.

4. Make the upsell after the original purchase.

One mistake I’ve noticed in some SaaS upsells is the way that they crush you with upsells before you’ve even completed your checkout.

For some customers, this is a pure, salesy turnoff. The number one reason that customers abandon shopping carts is because of added or increased prices. Upsells before checkout are risky at best.

As a simple alternative, I suggest upselling customers after they’ve made the purchase. To make it even easier, don't require customers to input their payment information again in order to complete their second transaction.

5. Sell something that solves a problem.

Here’s the interesting thing about most purchases. Even though they are intended to solve a problem, they also introduce additional problems.

  • You buy a burger. You want something salty and crispy. You want fries.
  • You buy a knife. It gets dull. You need a sharpener.
  • You buy software. You need to learn it. You buy training.
  • You buy sunglasses. They get fingerprints on them. You need a cloth to clean them.

Think carefully about the product you sell, and try to understand the new challenges or problems that it introduces. Then, upsell the customer on the solution to that new problem.

If nothing comes to mind, you can always introduce similar items. For example, Amazon offers customers a whole series of upsells and cross-sells.

  • “Frequently Bought Together”
  • “Customers Who Bought This Item Also Bought”
  • “Sponsored Products Related to This Item”
  • “Compare to Similar Items”
  • “Special Offers and Product Promotions”

You can always sell something. I suggest selecting a benefit-focused product that solves a real problem.

6. Eliminate risk.

Any successful selling process involves guarantees. With an upsell, this is more important than ever.

Customers are naturally on guard when they sense an upsell. If you can gain their trust through a bend-over-backwards guarantee, then your upsell will have a higher chance of success.


The great thing about upsells is not higher profit margins. Through an upsell, you also retain the customer longer.

Customers who buy more, stay longer. Not only do you earn more profits from superior sales, but you retain customers and combat churn. As long as you’re adding value with your superior product and strategic upsells, you’re going to have some very pleased customers.


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