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Sales - 11 min READ

How to upsell: 11 ways to do it without being pushy

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Author photo: Amy Copadis

Amy Copadis


Often, people associate upselling with an underhanded sales technique that tricks customers into spending more money than they want to (or need to).

Upselling has a bad rap, and it’s the sleazy salespeople of the world that have created it.

But upselling can do great things for your business without ruining your brand. In fact, one company’s upsell program enabled them to triple their revenue.

Even better, upselling can actually help you build better relationships with customers, and boost customer loyalty.

Let’s look at why learning how to upsell is so important, and some specific strategies you can use to upsell without being pushy.

What is upselling?

Upselling is when you sell a more expensive version of a product to a current customer.

For SaaS companies, this could mean selling an upgrade of your product that offers more features, allows for more users, or provides training on how to use your product. For physical product sales, upsells could include a more expensive version of the same product (e.g. the same car, but with heated seats and a sunroof), or an extended warranty.

Closely related to upselling is cross-selling, which involves selling an additional, different product to a current customer, but one that is probably related to their first purchase.

Here’s the catch: for your upsells to work (and not annoy your customers), you need to provide them with something that is genuinely valuable to them as an individual.

So, why is learning how to upsell so important for you and your sales team?

What are the benefits of upselling?

Upselling can help you build deeper (and more valuable) customer relationships.

When you upsell to customers, you’re not just trying to get more dollars tacked on their bill: you’re also trying to provide value to them.

When you offer upsells that are useful and relevant to each individual customer, they’ll appreciate these efforts rather than see them as a scheme to get them to cough up more cash.

Providing genuine value to your customers is one of the biggest factors in building customer loyalty.

Upselling is easier (and more profitable) than selling to new customers.

According to the book Marketing Metrics, the probability of selling to a new prospect is only 5-20%. However, the probability of selling to an existing customer can be up to 70%.

By upselling to existing customers, you’re also saving on marketing and selling costs. In fact, one study of SaaS companies found that it costs $1.18 to earn $1 from new customers, while it only costs $0.28 to earn $1 through upsells.

If you want to build customer loyalty, increase lifetime customer value, and sell easier, it’s time to learn how to upsell.

Here are 11 tips you can use to successfully upsell customers.

1. Align your upsells to the customer’s needs and goals.

All of your customers are unique. So, don’t try to fit them all into the same cookie-cutter upsell.

Let’s say you’re a SaaS company that offers three plans: the basic plan allows five users, the standard plan allows 20, and the pro plan allows 100. If you have a customer with 10 employees, don’t try to upsell them to the pro plan: they only need the standard plan.

To upsell right, you need to get into your customer’s head.

  • What are their company goals?
  • What are their current needs, and what do they foresee as future needs?
  • Where does your product or service fit into their goals?
  • How do their past purchases affect their future needs?

This kind of personalization in your upsells brings results: a study by Accenture found that 58% of customers are more likely to buy from a brand that recommends options based on their past purchases.

By aligning your upsells to the individual customer, you’ll show that you’re paying attention to their needs—not your own revenue goals. This, in turn, will build loyalty, and make them more likely to purchase the upsell.

2. Fully onboard customers before promoting big upsells.

How many upsells do your customers have to wade through in order to complete their first purchase?

If you bombard each new customer with tons of upsells before they’ve even made their first purchase, they may decide to leave without buying anything. This is especially annoying for the customer if the upsells aren’t 100% relevant to them and their needs.

That’s why it’s important to get through that first purchase before you offer any upsells. Or, if a relevant upsell must be presented during the purchase process, make sure you only offer one upsell, and that it is truly valuable to the customer.

For example, look at how ProFlowers provides a quick and valuable upsell right when you add flowers to your cart.

This is a great upsell, because people generally don’t want to wait at home from 9 AM to 8 PM in order to receive flowers. The upsell is relevant, but also just as easy to accept or reject.

3. Design upsells that solve specific customer problems.

Allow customers to choose relevant upsells by designing multiple upgrades that apply to real problems that they’re facing.

For example, Trello does this in the way it offers integrations (or “Power-Ups”). All users can select Power-Ups for their boards, but the free users can only choose one Power-Up at a time.

However, Trello Gold users can have up to three Power-Ups per board, while Business Class users get unlimited Power-Ups.

This enables Trello’s customers to pick the upgrade that solves their particular problem.

Other companies can apply the same principle by creating upsells that play to specific issues that your customers face.

For example, why not offer on-site training to teach customers how to use your product effectively? Or, you could offer set-up plans that are basic or advanced, depending on how much help the client needs to get your product integrated into their system.

To find your own relevant upsell ideas, just think about the problems or concerns that your customers have. Then, offer upgrades that solve those problems.

4. Segment your customers to find more relevant upsells.

While each customer is a unique individual, they probably fit into related segments. Creating relevant customer personas is a great way to segment your upsells to the right customers.

For example, let’s go back to the example of the SaaS company with three different plans depending on how many users are needed. You could segment customers based on how many users they have. Then, you’ll know immediately who you can offer an upsell to.

5. Make sure the price is right.

How do you know if the price is right for an upsell?

In reality, it depends on your customers and your products. How much are your customers willing (or able) to spend on an upsell? And how much is your upsell actually worth?

If your customers are on a tight budget (and really, who isn’t?), that upsell will have to provide some serious value for them to even consider it.

But sometimes, even the perfect upsell is just too expensive for your customers. At this point, you may want to think about offering a discount.

As we mentioned above, it’s much cheaper and easier to sell to existing customers than to new customers. So, count the cost: see how much of a discount you can reasonably offer while still holding on to your profit. This is another way to build loyalty, since you’re offering genuine value with every offer.

Check out how GoDaddy does this when you purchase one of their hosting plans:

Obviously, it’s better for GoDaddy when their customers stick around longer. So, by offering big discounts for longer hosting plans, GoDaddy provides real value to their customers while winning more upsells.

6. Use milestones to promote upsell offers.

Once customers are using your product and are happy with it, they’ll be more likely to see the value of an upgrade.

For SaaS companies, in-app milestones can be great trigger points for upsells. For example, you could offer upsells when the customer:

  • Has been a customer for a few months or a year.
  • Has accomplished a certain number of tasks within your product.
  • Has spent a certain amount of time using your product.
  • Has seen significant ROI from your product.

These are great moments to offer upsells, because each moment is a sign that your customer is convinced of the value of your product.

That’s exactly how Asana slips in appropriate upsells. When you create an account with Asana and add a few tasks, they send an email that shows you just how much better it could be if you upgraded to Asana Premium.

This same idea could apply when your customers hit company milestones.

Continuing with our SaaS example above, let’s say a customer using the standard plan has recently acquired another small company. Now, their workforce has more than doubled, and their plan doesn’t allow enough users.

This would be an excellent time for a sales rep to reach out, congratulate them on the recent acquisition, and offer them an upsell to the pro plan that fits the number of people they have working for them. This is a relevant upsell that makes sense for their business.

Building and maintaining open communication with your current customers can help you spot the best moments for an upsell.

7. Include social proof.

Just like a first purchase, social proof is an important motivator in an upsell purchase.

Make sure the social proof is specifically relevant to the upsell you’re offering. For example, if you want a customer to upgrade to a more expensive plan, show them how other customers have improved an important metric (like productivity, revenue, or ROI) by purchasing the same upgrade.

Having the data to back up your statements will help customers see the value in the upsell you’re offering.

Again, Asana is a great example of upselling the right way. Check out the social proof that they include when upselling customers to their Premium plan:

Even just showing a star rating for the item can prove that other people found this purchase worthwhile.

8. Offer upsell bundles.

This combination of upselling and cross-selling can work very well for different types of businesses. Obviously, a brand that sells physical products can easily offer bundles that create savings for customers—but ultimately increase total purchase value.

Likewise, brands that sell services or SaaS companies can offer relevant bundles to their customers as well.

For example, why not bundle together certain add-ons that are frequently used together? A company that sells WordPress plugins could offer a bundle of three plugins that function well together.

Adobe uses this upsell method by offering major discounts on a bundle of all of their 20+ apps:

This upsell works because many people who use Adobe’s apps are likely using more than one. And if you’re already purchasing licenses for two apps, you might as well spend a little more and get the entire bundle!

Bundling products and services that are related is a great way to increase purchase value. To spice this up a bit, the discounted bundle could be offered only for a certain amount of time, combining a lower price with the fear of missing out.

9. Focus on what your upsell does for them.

When offering an upsell to a current customer, it’s important to start by focusing on what this upsell can do for them.

So, what kind of value can your upsell provide?

If you’re offering add-ons, don’t start by talking about what they are and what they do. Instead, talk about what they’ll help your customer to accomplish. What kind of problems would your upsell help them to solve? How can this upsell improve the business or workflow of your customers?

Focusing on these points will help convince your customers of the value of the upsell you’re offering.

Dropbox does a great job of this when upselling free customers to Dropbox Plus:

The message is clear: if you’re suffering from a lack of space for your files, Dropbox Plus is the way to go.

10. Add valuable upsells directly into the workflow.

Right inside the workflow of your product, you could provide opportunities for upsells. That way, customers are able to convince themselves that they need an upsell.

For example, look at how Canva does this with their Canva for Work upsell. When designing in the free version of Canva, there are options that trigger an upsell pop-up.

Each of these options has a symbol that shows it’s something you can only do when you’re paying for their premium plan.

While some users may never need to resize their designs, others absolutely need this upgrade.

Since the option to resize appears right in the workflow of the web app, users can clearly see the value that Canva for Work would provide to them, and may eventually convince themselves of the need to purchase the upgrade.

11. Know when to stop pushing.

There comes a point when upselling is no longer a loyalty-building strategy and turns into an ugly tactic that burns current customers.

Don’t be that salesperson who just won’t quit. Once a customer has said no to an upsell, don’t try to force it on them. Remember, down the road you can always offer it again at an appropriate time.

When you space out your upsells and know when to stop pitching (e.g. before the customer gets annoyed), you maintain healthy relationships with your current customers and leave the door open to future upsells.

Learn how to upsell the right way and you’ll win more loyal (and more valuable) customers.

Upselling, when done right, is a great way to increase revenue for your brand. Your current customers are the lifeblood of your company, and creating personalized, well-timed upsells that are relevant to their needs is a great way to increase their value to you.

Remember, relevancy is key. Make sure your upsells always solve a problem, and focus your pitch on how this upsell will benefit this customer.

When you learn how to upsell successfully, you’ll build lasting relationships that leave a good impression on your customers—and bring more revenue to your company.

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