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How to Upsell: 16 Best Upselling Techniques

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Upselling is a great way to increase your customers’ lifetime value, strengthen relationships, and even improve a customer’s experience with your business. 

And when implemented effectively, upselling doesn’t have to be awkward for the sales rep or annoying for the customer. In fact, upselling can be a key component of your company’s growth strategy.

Read on for tips on how to upsell and some of the best upselling techniques to keep handy.

What is upselling?  

Upselling is the process of persuading a customer to purchase an upgraded version of what they already want to buy. Sometimes upselling can also include selling a higher-priced product or service in addition to a customer’s purchase.

This practice is intended to increase the customer’s value and provide them with a solution better suited to their needs.

Upselling vs. cross-selling   

Upselling and cross-selling may be used at similar points in the sales process and for similar purposes, there are significant differences. 

Cross-selling is when a salesperson identifies two relevant products or services and sells them to the customer simultaneously, like a new cell phone and a drop-proof case. Cross-selling is all about increasing the value of a sale by adding more items to it like an add-on or similar product.

Upselling is focused on offering a more expensive version of something the customer already wants to buy, rather than convincing them to buy more. In the cell phone example, upselling is convincing the customer to buy a phone with 256GB instead of 128GB. At its core, upselling is about increasing the value of a sale by upgrading the product or service being purchased.    

Both of these techniques are useful for increasing a customer’s value, and they each have their place.

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The top 16 upselling techniques to drive revenue 

Want to help yourself and your sales team get better at upselling? The 16 upselling techniques below will give you a launchpad for nailing the upsell and generating more revenue 

Take a look at the upselling strategies below: 

1. Understand your customer’s needs 

Maybe the most important strategy for successful upselling is understanding your customers’ needs. Offering customers a more expensive product that doesn’t provide the features they’re looking for isn’t just aggravating—it could cost you their business altogether. 

Be sure you thoroughly understand the customer’s pain points. Then, you can communicate why the upgraded product is the best fit for their needs. 

For example:

I understand that your team uses different sales processes for customers in different industries. Our Enterprise plan offers unlimited sales pipelines, so you can design custom pipelines that fit each one of your processes.

2. Choose the right upsell 

Depending on your industry, offerings, and business goals, you may want to offer a different kind of upsell in different situations. Here are a few types of upsells you might want to use: 

  • The upgrade: The classic upsell, this strategy offers a premium version of the same product. Maybe it has more features, works faster, etc. 
  • Protection plan: A useful upsell for many kinds of products, extending a customer’s protection plan offers them the benefit of greater protection in case something goes wrong.
  • Extended service period: You can also offer extended onboarding, training, or product servicing for an upcharge. 
  • Customization: Offering product customization can result in a series of upsells if you charge for each type of customization requested. 
  • Bundling: Another popular upsell approach (that borders on cross-selling) is bundling, where you can sell customers on the value of buying multiple products together. 

3. Build trust

Trust is essential in sales, and especially in upselling. Many customers may be suspicious of upselling because they feel too much pressure or don’t feel that they really need the upgraded version. But when done right, upselling should feel more like a natural next step in a customer’s relationship with your company. 

The key is to focus on developing that relationship so your sales team can determine the best time to try upselling and frame the upsell as a solution to the customer’s needs. 

Developing good rapport with customers may take some time, but your team can use tools like text messaging, personal email sequences, and live chat to encourage stronger ties even when you’re not working face-to-face. 

4. Sell benefits, not features 

One of the best ways to sell, according to sales psychology, is to focus on benefits rather than features. Customers are frequently looking for a specific benefit rather than a specific solution—less stress at work, improved processes, or saving time and money. 

As a sales rep, it’s important that you sell your upgraded product or solution’s benefits, rather than just its features. Paint a picture of what life will look like with those benefits, and you’ll have your foot in the door on another upsell. 

5. Perfect your timing  

There are plenty of good upsell opportunities in a relationship with a customer (more on that later). And it’s critical to know when to bring out your upsell technique with different buyers. The timing of 

Never think of upselling as a shortcut that skips building the relationship and takes you right to higher revenue. Your client needs to be in the right position and state of mind to really hear your upsell as an opportunity to gain value rather than another sales tactic. 

It’s a good idea to give your product or service time to demonstrate its value before offering a higher-priced version. That way, the buyer is already sold on the value your product brings to their organization, and they’ll be more likely to pay for even greater value.  

6. Help customers upsell themselves 

Sometimes, you can even get customers to upsell themselves. How? By outlining all of their options and letting them see the difference in value for themselves. 

Do you offer multiple tiers of legal consulting services? Simply demonstrating that your highest tier offers the greatest level of involvement in a case could help clients decide whether to go for the premium offering. They know their own needs—sometimes they just need to see which solution fits them best.

Nutshell pricing plans for upselling

7. Avoid overselling

Similar to building trust with a buyer, you should also avoid overselling. If you push too hard, you (and your company) can come across as greedy and inconsiderate. You’re neither of those things—so demonstrate it by knowing when to stop selling. 

It’s important to accept your customer’s answer. You don’t want to risk their business entirely by pushing them to purchase something they aren’t ready for or don’t need. Give them some resources for further consideration, and then give them space. 

8. Use the right amount of pressure 

As mentioned above, it can be easy to overdo it when encouraging customers to buy a premium product or service. But you do need to apply some pressure. 

Develop the skill of being able to read a customer’s reaction to you and your product. If you run an eCommerce business, adding upsell popups right when a visitor lands on your page is likely to turn them away. But if you suggest an upsell during checkout or after they’ve added an item to their cart, they’re more likely to go for the upgrade. 

9. Be flexible  

You know you’re a great salesperson, and you have some winning upsell techniques under your belt. But don’t be stubborn if a strategy you’ve chosen doesn’t seem to be working. You need to master the ability to pivot and offer a different option quickly, before your customer loses interest. 

Keep the conversation educational rather than salesy to demonstrate that you have the buyer’s best interests at heart. And be flexible enough to change your offer when needed.

10. Make it easy to say “yes”  

Upgrading to a premium product is much easier under the right circumstances, and you can influence how easy it is for a customer to say “yes.” 

At strategic points in your conversation, ask questions like: 

  • Am I understanding your needs correctly? 
  • Was that example helpful? 
  • Does that solution sound beneficial?
  • Does that work for you? 

By getting customers on a loop of nodding and agreeing with you, you make it easier for them to continue responding the same way.  

11. Clearly compare your offerings 

A common pitfall in upselling is failing to clearly make the distinction between your offerings. After all, why would a buyer spend more money on a product that looks nearly identical to the one they already have? 

Whether you’re on a sales call or designing your company’s website, it’s important to clearly explain the differences between your products or service tiers. Use visual cues like comparison tables and highlighting to reduce decision fatigue and showcase the benefits of your higher-priced options.

iphone pricing comparison for upselling

12. Incentivize upselling 

Incentives can be a powerful way to encourage upselling. Offering incentives can help make it easier for customers to upgrade and even offer a good feeling when they do. Just use incentives strategically and make sure they deliver a sense of value rather than cheapening your offerings. 

Incentives for upgrading could include: 

  • Discounts 
  • Free shipping 
  • Buy two, get one free
  • Loyalty rewards
  • Free onboarding services 
  • Free support services
  • Reduced pricing if paying annually 

13. Optimize your customer service 

Upselling shouldn’t rest entirely on the shoulders of your sales team. Customer success and support teams are also in a great position to educate customers on your premium offerings, as they often work more closely with buyers over the long term. 

Your support and success teams should build on the relationships your sales team established and foster even stronger trust with customers. Look closely at your customer service team to identify areas of improvement and opportunities for implementing upsell strategies. Often, making upsell recommendations can be a natural part of these interactions.     

Is a customer struggling with an integration they currently have with your software platform? Their customer success representative can offer your company’s alternative. Has a buyer routinely expressed frustration with a lower-quality product? Customer support can point out the benefits of upgrading to the premium version. 

14. Value and leverage feedback  

Customer feedback is a valuable source of growth opportunities. When buyers share their feelings and opinions about your products or services, take note! That feedback could be an opportunity for suggesting an upgraded version or relevant product that meets the buyer’s needs. 

15. Bring out the social proof  

Social proof is a highly valuable tool in sales and marketing. Demonstrating that your solution has worked for others makes it easier for customers to imagine that it will work for them. And upselling is a great chance to bring out your testimonials, case studies, and reviews. 

Social proof frequently works because it appeals to emotion. People trust the opinions and experiences of others. Placing social proof at strategic places on your website or in email marketing campaigns can be the push people need to buy the upgraded product.

16. Follow up via email    

When it comes to keeping in touch with customers so you can seize every upsell opportunity, email marketing is a powerful tool. Many customers prefer to communicate with businesses using email, and with segmented audience lists and automated drip campaigns, email lets you stay connected with minimal effort. 

Use emails to offer upsells or even remind buyers of premium products after they’ve said no. You can also use emails to advertise new products or services that customers might be interested in.

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How to find opportunities for an upsell  

So when should you upsell? It might depend on your customer. Here are a few common times in a customer relationship where you might want to offer a premium option:

  • Before the sale: Before the buyer has even made their purchase, it’s a great time for an upsell. Present your offerings on a price and feature spectrum, which often encourages customers to pick something in the middle. Or if that option doesn’t provide the benefits they’re looking for, you can encourage a higher-priced alternative. 
  • During checkout: Whether you’re finalizing the sale in person or online, checkout is another good time to display your company’s other offerings. The customer has already demonstrated significant interest in your products, so they’re likely to take a second look at any other options you present to them.
  • After the purchase: Highly engaged customers are great candidates for upsells, as they’re already finding value in your product or service. 

Use upselling to strengthen customer relationships 

When done strategically, upselling is an effective way for your sales, success, and support teams to increase customer lifetime value and build better customer relationships. Buyers will get more value from your company and feel understood, and may even become advocates for your business. 

Another powerful way to fortify your customer relationships is with a CRM. The best CRM is the one that provides the features, tools, and support your team needs at the right price for your organization. 

Nutshell is the all-in-one CRM solution that hits the sweet spot for all of those essential needs. With critical CRM tools like pipeline management and sales automation, plus advanced features including email marketing, prospecting, and integrations with your tech stack, Nutshell empowers your team to sell better. 
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