Rome wasn’t built in a day. Historians estimate the Roman empire took 800 years to reach its peak.

For many teams, it can feel like a sales cycle is equally long. 75% of B2B companies take at least 4 months on average to win a new customer. Now if you have a B2C product, your time to acquire a customer is likely significantly less. However, your customer acquisition costs (CAC) may be anywhere from $80 to hundreds per customer. 

This is just one of the pivotal reasons businesses develop upselling strategies. After putting that much time and resources into closing customers, many brands rely on upselling to increase their bottom line.

In this guide, we’ll share everything you need to know about upselling and provide techniques your team can use to grow your sales-assisted revenue. 

Let's dive in.

Upselling Upselling

What is upselling

Upselling is a sales technique centered around increasing your customer's average sales value. With upselling, you convince your customers to buy a more premium version of your product or service to earn the most profit. SaaS companies and productized companies selling high-end items often use upselling. 

Let's say you have a SaaS product. During a sales demo, highlighting the premium features of your product such as integrations is one way you can upsell. 
Depending on your organization’s revenue model, you can bring up your annual recurring revenue or average sales order from a customer by upselling — while spending less than you would on CAC expenses.

It's a win/win for everybody. It doesn't require more emails, ad spend, or anything else,” said Kate McKibbin on her podcast, Doing It Online

One study found upselling existing customers is 68% more cost-effective than acquiring new customers. The average SaaS company generates 16% of new Annual Contract Value (ACV) via upselling existing customers.

Upselling vs Cross-selling

Cross-selling focuses on providing personalized and related product or service recommendations to capture more revenue. Like upselling, cross-selling aims to increase revenue by capitalizing on the customer’s active interest in your business.

One cross-selling technique is to show the product recommendations during check out, encouraging customers to purchase additional items related to their current purchase.

For example, think about the last item you purchased on Amazon. Directly below the main photos of that item, Amazon likely recommends other related items to bundle and purchase. So if you’re checking out kitchen pans, Amazon may also recommend buying spatulas. 

eCommerce brands often use a combination of upselling and cross-selling to drive more revenue. Cross-selling is also very popular with banks, insurance agencies, and EdTech companies. 

Upsell vs Cross-sell Upsell vs Cross-sell

When to upsell to a customer

Not sure what’s the best time to upsell a customer? Here are four approaches to help you identify existing customers who will be more likely to spend extra.

Proven customers

Your proven customers involve anyone that’s used your product for a while and are seeing success. As you test out upsell techniques, you can track how long a customer needs to be with you and how much success they need to see before they’re more likely to purchase more from you. Then iterate on your upsell techniques (keep reading as we share specific upselling techniques). 

Brand champions

If you see a customer who can give you a warm introduction, just ask. Build requesting referrals into your sales process. 

Consider also seeking out customers already referring other businesses to you. Most leads call out when they’re referred by someone else, so review the information captured in your CRM. 

Companies providing you with more business are the ones experiencing the most perceived value from your services. They are prime to sell to if you have a relevant offer.

Scaling teams

Another clear contender for upselling is customers you can see based on any number of growth factors. A team may expand quickly after they received an investment such as a Series A. Your company may even have an existing offering that provides more advanced solutions that help accelerate its growth.

Another clear sign that a customer is scaling: if the amount they’re spending on your product or service increases over time. For example, if the number of users subscribed to a SaaS product doubles in a year.

Using CAG framework

Consider also structuring your upselling strategy around the CAG framework.  This method involves analyzing:

  • How much (or how often) a customer consumes your product/service?

  • What features have they adopted?

  • Where can you fill the gap?

Over time, you’ll be able to see more clearly what successfully upsold customers have in common. Then you can finetune when to upsell further. You may find specific events need to happen first before you can upsell.

5 Upselling techniques with examples

Now that you have a better sense of whom you can upsell, let’s look at specific upselling techniques. 


1. Leverage data you have about your customers

Your CRM, helpdesk and any tools used by your customer success team contain quantitative data you can use to implement actionable insights.

But don’t forget qualitative data readily available from your team whether it’s a support rep or customer success manager. They can help confirm a customer’s current needs — and if a customer isn’t happy with the services provided.  

"The one thing that most companies don't leverage enough is the data we already have about them,” says Irit Eizips, Chief Customer Officer & CEO at CSM Practice.

Iris recommends using this data for upselling roughly a year from a sales handoff and implementation of your services.

Upselling - Leverage data you have about your customers Upselling - Leverage data you have about your customers

2. Nurture existing customers

Checking in with your current customers is one of the simplest ways you can strengthen relationships with them. Ask them questions via surveys to find out a customer’s experience with your product/service, what product improvements they would like to see, current challenges, and gauge how upgrading will help.

From your surveys, you may take those learnings and develop a more premium version of your offer you can upsell to include

  • In-depth product training delivered by a customer success rep
  • On-site implementation
  • Additional usage allowance for a specific feature

Showing you are making continual improvements to your services can also help engage existing customers. This includes email campaigns containing regular feature updates that highlight benefits using similar phrases to what your customers share in surveys. 

Nurture customers Nurture customers

As you re-engage customers through email, you’ll discover specific customers are more receptive to your campaigns. Segment your customers into different buckets. This can be based on their engagement level and interest. 

Are you seeing certain topics or emails that drive consistent click-throughs to your website for some customers you want to upsell? Run personalized campaigns using sales sequences containing the most relevant resources based on their browsing history and product usage.

3. Make your upsell relevant

Relevant upsells aren’t just a preference for specific personas. An Accenture study found 91% of consumers are more likely to shop with brands that provide relevant offers and recommendations.

This isn’t just a B2C-specific phenomenon; B2B brands can showcase relevant features based on the existing customer research. If your product targets sales, you can start with one layer of personalization based on their role and what features matter most to them. You could also display the features between different product versions in a side comparison, showcasing what they stand to gain by upgrading to a higher version.  

Then personalize the upsell experience based on the information you have in your CRM and other analytics. Go beyond their identified requirements. See what other problems they might be facing and how you can help. The most effective approach to selling will always be consultative. 

Upselling - Make your upsell relevant Upselling - Make your upsell relevant

4. Use urgency coupled with discounts and offers

Set limited-time offers, discounts, and incentives to push your customers forward on your upsell. In an online store, you can present this offer during checkout or after a customer purchases. 

For example, FlumeWater offers a home water monitoring system for usage and leaks. At checkout, they offer an annual subscription program that includes all their base features plus: 

  • 15% off leak repair services 
  • Custom budget and leak alerts 
  • Data on water usage indoor vs outdoor

Over 10,000 customers have taken advantage of the offer according to an interview with ​​Co-Founder of Flume, Eric Adler. At $200 per sale, that’s over $500K in extra revenue — just from one upsell. 

Upselling - Use urgency coupled with discounts and offers Upselling - Use urgency coupled with discounts and offers

In a more direct touch sales environment, this involves suggestive selling. Suggestive selling is a sales technique where a salesperson asks a customer if they'd like to include an additional product or service, along with their primary purchase. This could be add-on functionalities, extended warranty, product training, etc. 

The key to making this technique work is having in-depth knowledge of what you’re selling. That way, you are only offering an upsell where it makes sense for the customer and you can develop trust. One study found 82 percent of consumers are more likely to listen to the recommendations of an expert. 


5. Share social proof 

Showcase other customers who have used your more premium product or service — and most importantly, the results they’ve seen.

Gather testimonials and develop case studies from the brand champions you identify. Then incorporate these into your landing pages and email marketing to deliver relevant social proof.

Check out how Freshsales has gathered social proof from customers of different industries.  



By testing different upsell techniques and documenting your upselling strategy, your team can improve your business’s bottom line. Like any growth goals, all tests you run should tie back to KPIs you can track. 

The right CRM can help you not only track key sales metrics, but also visualize that information through analytics and visual reports—making it easier to find trends and identify opportunities for growth.

Freshsales can help you do all of that and more.

Sign up today to start your 21-day free trial.

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