How to Train Your Staff to Spot Upselling Opportunities

If the word "upsell" makes your staff cringe, you are not alone. Tennis club employees, academy staff, and even coaches often think of upselling as pushy or awkward. But when done right, upselling is not sleazy—it is service.

The key? Training your team to recognize upselling as a value-add, not a sales gimmick.

In this guide, we will walk through a complete strategy for training your staff to confidently and authentically recommend upgrades, add-ons, and services that improve your customers experience—and boost your bottom line.

Why Upselling Matters in the Tennis Industry

Tennis is not just a sport—it is an experience. When someone signs up for a lesson, buys a product, or joins your club, they are looking for more than court time. They want results. They want community. They want to improve.

That means they are open to buying more—if it helps them get there.

Effective upselling:

• Increases average customer value
• Improves customer satisfaction (yes, really)
• Builds loyalty by providing customized solutions
• Strengthens the financial health of your business

If your staff avoids upselling, you are likely leaving money—and customer value—on the table.

Step 1: Redefine What “Upselling” Means

Before you can train your team, you need to reframe the concept of upselling.

Most people associate upselling with annoying sales tactics. Think fast food chains asking, "Do you want to super-size that?" or stores pushing extended warranties.

That is not what you are doing.

At your tennis business, upselling means offering something that genuinely benefits the client—whether it is a private session, a racquet upgrade, or early access to a popular clinic.

Train your team to think of it this way:

• You are not “selling” something extra.
• You are recommending something better.

Your job is to educate, not pressure.

Step 2: Teach Your Staff to Recognize Triggers

Your staff will never upsell if they do not know when the opportunity presents itself. This is where real training comes in.

Here are some common upselling triggers they should listen for:

🎾 For Front Desk Staff:

• A parent says: “He really wants to improve his serve before tryouts.”
  → Recommend: private lesson package or serve-specific clinic
• A new visitor asks: “Do you offer anything beyond group classes?”
  → Recommend: tiered memberships or small group training
• Someone is checking out at the pro shop and mentions: “My hand is getting blisters."
  → Recommend: getting some new grips from the pro shop and you'll be happy to put it on their racket

🎾 For Coaches:

• A student seems frustrated or bored in group class
  → Recommend: 1-on-1 lesson or a challenge match session
• A player has plateaued
  → Recommend: video analysis or custom drills
• A parent asks: “Do you think she is ready for tournaments?”
  → Recommend: competitive prep training package

Give your team real examples and even scripts to help them practice listening and responding naturally.

Step 3: Roleplay Regularly (Yes, Really)

This is the part most managers skip—and it is also the part that works. If you want your team to feel confident recommending something, they need to practice it. During your next team meeting or training session, try this:

• Split into pairs.
• One person is the customer, the other is staff.
• Give the “customer” a scenario (for example: “You just finished a free intro class and want to keep learning”).
• The “staff” member has to recognize the opportunity and respond with a helpful recommendation.

Debrief as a group. What felt natural? What sounded awkward? How could the suggestion be more helpful?

Do this often. The more your staff practices, the more comfortable it becomes.

Step 4: Build a Menu of “Easy Wins”

Make it easy for your team to remember what to recommend.

Create a cheat sheet with 5–10 upsell opportunities that feel natural, useful, and non-pushy. Post it at the front desk, include it in staff onboarding, and talk about it in team huddles.

Here is an example menu:

Situation	Easy Upsell
Parent of beginner	Private starter lesson bundle
Student in group class	Add 1 private per month
Someone buying a racquet	Add a stringing package or overgrip bundle
Tournament player	Offer a video review session

Having these options in writing removes the guesswork and increases consistency across your team.

Step 5: Position Upsells as Service, Not Sales

This is where many businesses mess it up. They tell their staff to “push memberships” or “sell more packages”—and then wonder why customers feel annoyed.

Instead, use language that emphasizes benefit.

For example:

• “A lot of players like you have found that adding one private lesson per month helps them progress faster.”
• “You might like this prep clinic—it is designed specifically for players getting ready for USTA events.”

None of that sounds salesy. It sounds like you are paying attention and offering a smart next step.

Train your staff to use suggestive, benefit-driven language, not pushy tactics.

Step 6: Tie Upselling to a Bigger Vision

Upselling should not feel random. It should be baked into your culture.

Frame it like this:

• We are in the business of helping players grow and perform.
• Our job is to guide them to the right tools, services, and experiences.
• When we upsell the right way, we are helping—not selling.

This is not about hitting quotas. It is about matching people with what they need next.

Step 7: Reward and Recognize the Right Way

Your team will prioritize what you measure. If you only reward sales volume, staff might get pushy or weird. Instead, reward helpfulness, listening skills, and customer outcomes.

Ideas:

• Monthly “Customer Hero” award for best upsell story (staff explains how their recommendation helped a client succeed)
• Shoutouts in staff meetings for thoughtful recommendations
• Commission or small bonus on meaningful upgrades (like a $25 bonus for every private lesson package sold or new membership signed—not for pushing merch no one asked for)

Recognition makes it fun. Incentives make it stick.

Bonus Tip: Use Your Marketing to Set It Up

Your upselling strategy does not start at the front desk—it starts with your marketing.

If your website, emails, and social media posts explain your offerings clearly and show the value of premium services, it makes the staff’s job easier.

When a customer already knows about your tiered memberships or video analysis sessions, the staff is just helping them follow through.

Make sure your marketing content:

• Describes upsell options in benefit-focused terms
• Uses real success stories and testimonials
• Includes visuals (graphics, videos, charts) that show how different packages compare
• Promotes your most common upgrades ahead of time

Think of it as pre-selling. Your staff just finishes the conversation.

Conclusion: Upselling It Is Not Sleazy—It Is Smart

When your team knows how to spot the right moments and recommend the right upgrades, everyone wins.

Customers get a better experience.
Your staff feels more confident.
Your business becomes more profitable and professional.

So train your team. Practice often. Keep the focus on service.

And remember—upselling is not about selling more. It is about helping more.

Need help mapping out your upsell strategy or training your team?
That is what we do at Resourcely® Marketing. We help tennis businesses grow smarter—with marketing, systems, and training that work in the real world.

👉 Reach out at resourcelymarketing.com.