Business Texting Handbook for Upselling

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Without consistent growth, a business won’t last. And we can’t understate the importance of customer acquisition. But too many leaders focus entirely on finding new customers. According to a report by Forbes, only a third of business leaders consider focusing on existing customers a priority. This is a problem. Successful sales teams should know how to provide more value to their current customers, and turn this added value into new revenue. We’re talking, of course, about upselling.

For too long, upselling has been a dirty word. It conjures up mental images of snake oil salesmen and infomercial hosts shouting, “But wait! There’s more!” It’s time to take a more accurate look at upselling and consider how to do it right. When done correctly, upselling is good for both your bottom line and your customers.

What Is Upselling?

Upselling is a technique that lets you generate sales by getting your current customers to purchase more. We don’t need to tell you that it’s more expensive to get new customers than to retain existing ones. Upselling is just the practice of putting that age-old business wisdom into action.

3 Steps to Follow for Successful Upselling

In order for upselling to work, you need to add it to your sales strategy in a way that feels organic to you and your customers. You do this by speaking to your customer base, actively listening, and understanding their needs.

1. Help Customers Find Initial Value in Your Product or Service

Upselling should start the moment someone purchases your product or signs up for your service. Don’t just come right out and say, “Thanks for your purchase! Here are some other products you may like!” That feels pushy. Instead, help your customers get as much use as possible out of the product they just bought. Someone who’s happy with their current service is likely to invest more money in it later. At the minimum, do the following:

  • Have a support rep reach out and offer to answer questions
  • Provide free tutorials to get customers familiar with the product
  • Show customers how others have seen success with your product

2. Identify Opportunities to Provide More Value

This is where the active listening comes in. If you’ve done the first step correctly, you should have had a few productive conversations with your customers. During these conversations, you should consider what problems your customers need solved and how your product can help. At this stage, you can do the following:

  • Find common pain points your service or team can solve
  • Identify gaps in customer satisfaction
  • Ask what initiatives your customers have coming up

3. Take Action

It’s your turn to speak! You know what your customers need, now offer it to them. At this point, it shouldn’t even feel like selling anymore. If what you’re offering is truly valuable, your customers will feel like you’ve been proactively thinking about their needs. Now’s the time to:

  • Thank your customer for their loyalty and business
  • Offer additional services or larger packages
  • Explain how and why your customer should upgrade

What Text Messages You Should Send

Because you already have an established relationship, upselling should be easier than acquiring new customers or speaking to fresh leads. Especially if your product works well. Still, if you’re just starting to use texting to upsell, there’s some testing and learning you’ll have to do to iron out the kinks. Use these messages as a jumping off point:

Initial Offer to Help

Remember the first step, help customers find initial value? This is what that looks like. As soon as a new customer is acquired, have a member of your account management or customer service team reach out with a friendly welcome. This lets your customer know they’re cared about, and gives them an avenue through which to ask questions. When a customer can quickly troubleshoot any initial issues they experience with their service, they’re more likely to stick around.

Today 11:35 AM
Hi Will! This is Daniela from Commerce Labs. All of us here are excited for your online shop to launch.🙂
You should have received an email from us with a getting started guide. If you have any questions, feel free to shoot me a text and I’ll get back to you ASAP.

Two-Month Check In

Give your customers time to get familiar with your product before you start trying to sell them more. A one, two, or three-month check-in is a good chance to see how they’re doing. If they’re getting a lot out of your service already, consider telling them why it would be beneficial to upgrade. If the time isn’t right to upsell, use this as an opportunity to increase retention. Offer to help and show them how to take full advantage of your service.

Today 2:03 PM
Hey Will, Daniela again. 👋 Wanted to check in and see how things were going with your Commerce Labs account. Let me know a good time for a quick call.

Usage Limit Message

Many companies, especially those in the SaaS space, have different pricing plans. Each one with certain limits. Often times, there’s a free version for trial users that has limited functionality. When someone reaches one of these limits, tell them why and how to upgrade.

Today 1:15 PM
Hi, Will! It’s Daniela. I noticed you added the max number of products to your store 💪 Let me know if you’d like to upgrade to a higher package.

New Product Launch

Notice that none of the messages we’ve shown contain a “buy now” CTA or a payment link. They read more like ice breakers than sales messages. And that’s the point. The key to successful upselling lives in building relationships. Find opportunities to speak more frequently to your existing customers. One of these opportunities happens before you launch a new product. You’ll get valuable feedback from active customers, and they’ll feel like valued insiders. If they find your new product useful, they may even upgrade.

Today 2:00 PM
Will, we’d love your opinion. Are you interested in trying our AI-powered pricing calculator? It’s free for 2 weeks, and your feedback would be appreciated.

Better Pricing Plan

If you run a subscription-based business, most of your new sign-ups are probably monthly plans. But many customers sign up for a monthly plan without realizing down the line that they could benefit from a larger, annual plan. Improve cash flow and reduce churn by reminding customers why they should switch to an annual plan. They’ll appreciate the savings, and you’ll have more money upfront to go toward other growth initiatives.

Today 10:35 AM
Hi Will, happy 6-month shop-anniversary 🎉 Shops that are on the annual plan save 25%. Shoot me a text if you’d like to make the switch!

Seeing Results

Set benchmarks that allow you to quickly determine when a customer is seeing success with your product. If it’s an online school, it may be when they’ve enrolled in a second course. If it’s website building software, it could be when they’ve received a certain amount of visitors. These checkpoints are a good time to offer more service or products to customers.

Today 1:18 PM
Looks like you’ve really grown sales recently. 📈 Let’s chat about how you can keep up with our Commerce Labs Pro plan. Available today for a quick call?

Do’s and Don’ts of Upselling Using Text Messages

The messages above should help you grow your business naturally. But don’t confine your upselling texts to the messages we’ve listed. Connect with your sales, account management, and customer service team to talk about how you can better serve your users. Just be sure to keep the following in mind:


  • Apply a one-size-fits-all to customers
  • Go for quick, short-term wins
  • Be pushy or make customers feel pressured


  • Personalize your messages (even if you’re using templates)
  • Have patience and be friendly
  • Focus on starting conversations
  • Show your customers how to find more value in your product
  • Transition important sales conversations to phone calls

In Conclusion, Let’s Not Call It Upselling Anymore

Even if someone is ready to make a purchase, no one wants to feel like they’re being sold to. Your customers have challenges and problems. You have solutions. So let’s stop calling it “upselling” and start calling it “problem-solving.” (Yes, it’s a little corny 🌽) But remember, all of the steps in the process, even the ones where you’re not closing a sale, are important to growing your business and keeping your clients happy.

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