How to Offer Exclusive VIP Upgrades Using Cross-Selling and Upselling?

I’d just wrapped up creating a 4-week productivity course and was honestly just proud to get it out the door. But about a week after launching, I had a few people reach out saying, “Do you have anything more advanced?” and “I wish this came with 1:1 feedback.” My gut reaction? Mild panic. I didn’t want to rebuild the whole thing from scratch.

That’s when I realized… I didn’t need to.

I just needed to create a VIP version and use cross-selling and upselling to offer it at the right time.

Why VIP Upgrades Work So Well? (And Feel Premium)

First off, people love to feel special — we all do.

A VIP upgrade doesn’t just mean more content. It means more access, more support, more transformation. That’s what people are really paying for.

And when you position it correctly, it doesn’t feel like a hard sell. It feels like a natural next step.

Here’s what I included in my VIP version:

• The core course (obviously)

• 2 live Q&A sessions via Zoom

• A private Notion dashboard with bonus templates

• Voxer support for 2 weeks

I priced it at 3x the regular course — and still had people choosing it without hesitation.

If you’re curious about how to write persuasive upgrade offers, check out how to write high-converting upsell copy to see exactly what language actually moves people to buy more.

Where Cross-Selling and Upselling Come In?

So, let’s break this down a bit.

Cross-selling is when you offer complementary products (like “add these templates to your course”).

Upselling is when you offer an upgrade or premium version of the product they’re looking at (like “go VIP for live coaching and bonus resources”).

To create a seamless upgrade path, I added:

• A “Go VIP” section right under the buy button

• An email follow-up for buyers of the regular course

• A cart bump offer (literally a checkbox that said “Add VIP coaching for $147”)

This wasn’t fancy — just intentional.

Want help coming up with your own ideas? Here are 15 best cross-sell products for digital creators from real experience to help you brainstorm what extras make sense for your audience.

Lessons I Learned (the Hard Way)

• Timing is everything.
  Don’t push the VIP upgrade immediately. Let the regular offer breathe, then present the upgrade.

• Clarity beats hype.
  My first version had fluffy language like “unlock your highest potential.” Meh. The better version said: “Get two live Zoom calls, bonus Notion templates, and 2 weeks of Voxer coaching.”

• Make it feel exclusive.
  I capped the VIP spots at 15 people. That wasn’t just a sales tactic — I literally couldn’t handle more calls. But it worked wonders. People love limited offers. Need help framing urgency the right way? These limited-time upsell offers that convert are a goldmine of ideas.

• Use automation.
  I used ConvertKit to send a time-limited VIP offer email 48 hours after purchase. No spam, just a “Hey, want more support?” nudge.

A Few VIP Upgrade Ideas You Can Steal

Whether you sell digital products, services, or courses — here’s how you can cross-sell or upsell into VIP upgrades:

• For a course: Add a VIP tier with coaching, templates, or live feedback

• For a service: Add premium turnaround time, extra deliverables, or bonus calls

• For digital downloads: Bundle extra resources, swipe files, or tutorials

• For memberships: Add private Slack/Discord access or behind-the-scenes content

You can present these:

• On your product page as an upgrade option

• At checkout with a cart bump

• Post-purchase with a thank-you page offer

• In an email funnel after someone buys the basic offer

Not sure when or how to present these offers? Here are 9 best upselling techniques for online stores that work across many business models — especially digital ones.

What Actually Converts?

I tested a lot of stuff — here’s what worked best for me:

• Short, bullet-style feature lists (people don’t read long paragraphs)

• Urgency without pressure (“VIP access closes in 3 days” works better than “Buy now or lose everything”)

• Testimonials from VIP clients (even 1 or 2 makes a big difference)

• One-click add-to-cart buttons — the less friction, the better

And honestly? Keep it simple. One mistake I made early on was offering 3–4 different VIP options. That overwhelmed people. Now, I keep it to just one clear upgrade.

If you want to take your strategy to the next level, don’t miss these 11 case studies of successful upsell strategies that actually worked. It’s one of the best ways to learn what converts without guessing.

Final Thoughts

Offering a VIP upgrade doesn’t have to be complicated. Start with your current offer. Then ask: What would make this feel 10x more valuable to someone who really wants results faster or with more support?

That’s your VIP offer. From there, it’s just a matter of smart cross-selling and upselling — making sure people see the offer at the right moment in their journey.

Don’t overthink it. Make it clear. Make it real. And remember, some of your best customers want to pay more. You just need to show them how.