The 30% Upselling Strategy That’s Hiding in Plain Sight

The most overlooked upselling strategy in sales might be the simplest one you’ve never fully embraced.

When I was writing my book, “The Sales Multiplier Formula”, something jumped out at me that I hadn’t really noticed before: You can increase your sales by 30% strictly by focusing on an upsell.

That’s not a typo. Thirty percent.

And here’s the kicker — Most salespeople are leaving this money on the table every single day because they’re not taking this simple proactive selling approach.

Why This Upselling Strategy Works Every Time

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Think about it. When was the last time you walked into a restaurant and the server didn’t mention appetizers, desserts, or premium drink options?

They do it because it works. Your prospects are no different — they’re curious about what else you offer, especially the premium options.

Here’s the fundamental three-step process that changes everything:

1. Identify your next-level offering — What’s the premium version of whatever you’re selling? Products, services, equipment, insurance policies — there’s always an upgrade.
2. Always mention that options exist — This is where most salespeople fail. They present one solution and stop talking. Don’t do that.
3. Present the premium choice with confidence — You’re not being pushy, you’re being helpful. You’re showing them what’s possible.

When you mention options during your conversation, you automatically position yourself as consultative rather than transactional. Your prospect thinks, “This person is showing me choices, not trying to ram one solution down my throat.”

How One Insurance Agent Mastered This Upsell Approach

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Let me tell you about Sarah, an insurance agent who was struggling to hit her numbers. She was great at selling basic coverage but never mentioned premium options because she assumed that her clients couldn’t afford them.

I challenged her to change her approach. Instead of saying, “Here’s your basic coverage,” she started saying, “I have a few coverage options for you. Let me show you the standard package first, and then I’ll walk you through the premium option that includes additional protection.”

Within 60 days, her average sale increased by 28%. Why?

Because 4 out of 10 prospects asked about the premium option. Half of those upgraded on the spot.

Sarah had been leaving thousands of dollars on the table every month simply because she wasn’t mentioning that options existed.

The Upselling Strategy Mistakes That Kill Your Close

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Here are the three mistakes that sabotage your upsell success:

• Assuming prospects can’t afford premium options — Stop being their financial advisor. Let them decide what fits their budget.
• Forgetting to mention options exist — If you don’t tell them, they’ll never know. It’s that simple.
• Treating upsells as afterthoughts — Present them with the same confidence as your main offering. If you sound apologetic or uncertain, they’ll pass.

The fix for all three? Practice your options language until it feels natural.

“I have a few different packages” or “Let me show you what’s available” should roll off your tongue.

Try This Upselling Strategy Today

Here’s your challenge:

1. Right now, identify your premium offering.
2. Write down exactly how you’ll mention that options exist in your next three sales conversations.
3. Practice it out loud.
4. Then go use it.

You’ll be shocked at how many prospects ask about the higher-value options.

This upselling strategy isn’t rocket science, but it works. Thirty percent growth is sitting there waiting for you.

The question is: are you ready to stop leaving money on the table?

© Shawn Casemore 2025. All Rights Reserved.