How to Upsell Existing Students with Bundles (Without Being Pushy)

You’ve put in the work—created an amazing course, built a loyal student base, and now you’re seeing steady enrollments. But here’s the thing: your existing students are your most valuable asset. They already trust you, love your content, and are primed to buy more from you.
So, how do you upsell them without feeling salesy?
The answer: Course Bundles.
Bundling isn’t just about slapping two courses together and calling it a deal. It’s about delivering more value, solving bigger problems, and making it a no-brainer for your students.
In this post, we’ll break down:
✅ Why bundling works (hint: it’s not just about making more money)
✅ How to segment your students so your offers feel personalized
✅ The best types of bundles that actually convert
✅ Real-world examples from entrepreneurs who’ve done it successfully
Plus, we’ll show you how to turn this into a passive income stream—because who doesn’t love making money while they sleep?
Let’s dive in.

Why Course Bundling is a Game-Changer for Online Entrepreneurs

Think about the last time you bought something online. Did you go for the single product or the bundle that gave you more for less?
Most people choose bundles because:
✔ They feel like they’re getting a deal (even if they were only planning to buy one thing).
✔ It solves multiple problems at once (instead of piecing together solutions).
✔ It removes decision fatigue (fewer choices = faster purchases).
For you, bundling means:
🔥 Higher revenue per student (instead of a one-time $50 sale, you could make $150+).
🔥 Better student results (when they buy multiple courses, they get better outcomes).
🔥 Stronger loyalty (students who invest more stick around longer).
But here’s the key: You can’t just throw random courses together and expect magic.
Let’s talk strategy.

Step 1: Segment Your Students for Laser-Targeted Offers

Not all students are the same. Some are just starting, while others are ready to level up. The right bundle for one group could be irrelevant for another.
Here’s how to segment your audience:

1. By Skill Level

• Beginners: Bundle an intro course with a quick-win mini-course.
  (Example: “Social Media Basics” + “5-Day Instagram Growth Challenge”)
• Intermediate: Pair a core course with an advanced module.
  (Example: “Email Marketing 101” + “Automated Sales Funnels”)
• Advanced: Offer a high-ticket mastermind add-on.
  (Example: “6-Figure Copywriting” + “1:1 Coaching Session”)

2. By Engagement

• Active students: Offer a “next step” bundle based on their progress.
• Lapsed students: Re-engage them with a “catch-up” bundle at a discount.

3. By Goals

• Want more clients? Bundle a lead-gen course with a sales script template.
• Want passive income? Pair a course with a done-for-you affiliate setup.
  Pro Tip: Use your email marketing tool (like ConvertKit or ActiveCampaign) to tag students based on their behavior. Then, send hyper-relevant offers.

Step 2: Choose the Right Type of Bundle

Not all bundles are created equal. Here are the 3 most effective types (with examples):

1. The “Complete Solution” Bundle

Combine courses that solve one big problem from start to finish.
✅ Example:
– Course 1: “YouTube Growth Secrets”
– Course 2: “Video Editing Mastery”
– Bonus: “30 Viral Video Ideas”
Why it works: Students don’t just want knowledge—they want done-for-you results.

2. The “Time-Saver” Bundle

Package courses that help students achieve results faster.
✅ Example:
– Course 1: “Pinterest Traffic Blueprint”
– Course 2: “Canva Templates for Bloggers”
– Bonus: “30-Day Content Calendar”
Why it works: Busy students love shortcuts.

3. The “Exclusive Access” Bundle

Offer a limited-time bundle with bonuses they can’t get anywhere else.
✅ Example:
– Course 1: “Freelance Writing Foundations”
– Course 2: “High-Pitching Clients”
– Bonus: “Live Q&A with Top Freelancers” (only available in the bundle)
Why it works: Scarcity = urgency.

Step 3: Price It Right (So It’s a No-Brainer)

Pricing can make or break your bundle. Here’s the formula:
Original Price of Course 1 ($97) + Course 2 ($97) = $194
Bundle Price = $147 (25% discount)
But don’t stop there. Add a bonus (like a cheat sheet or live call) to make it irresistible.
Pro Tip: Test different price points. Some students prefer a payment plan ($49 x 3) over a lump sum.

Step 4: Promote Your Bundle the Right Way

You could have the best bundle ever, but if no one knows about it, it won’t sell. Here’s how to get it in front of the right people:

1. Email Your Existing Students

• Subject line: “Your Exclusive Upgrade is Ready”
• Body: “Hey [Name], since you loved [Course 1], I thought you’d love this…”

2. Use In-Course Upsells

Add a “Recommended Next Step” module at the end of your course with a CTA to the bundle.

3. Offer a Limited-Time Discount

• “Only available until Friday!”
• “First 50 students get a bonus coaching call.”

4. Leverage Your Community

If you have a Facebook group or membership site, share student success stories from those who bought the bundle.

How to Turn This Into a Passive Income Stream

Once you set up your bundles, they can sell on autopilot. Here’s how:
✅ Use a course platform (like Kajabi, Teachable, or Podia) to automate delivery.
✅ Create evergreen sales pages so students can upgrade anytime.
✅ Set up email sequences to promote bundles after course completion.
Real-World Example:
One BizWiz Academy member bundled her “Instagram Growth” course with a “Reels Masterclass” and made an extra $8,000 in 30 days—just by emailing existing students.

Final Thoughts: Start Small, Scale Fast

You don’t need 10 courses to start bundling. Even if you only have two courses or a course + a workbook, you can create a high-value offer.
Action Steps:
1. Pick 2 related courses (or a course + bonus).
2. Price it at a discount (but still profitable).
3. Promote to your warm audience first (email, community, in-course upsells).
4. Track results & optimize (try different bundles and pricing).
Remember: Your students WANT to succeed. By bundling, you’re not just making more money—you’re helping them get better results, faster.
🚀 Ready to bundle your way to higher revenue? Start today—your students (and your bank account) will thank you.

P.S. Want more strategies like this? Join The Biz Wiz Academy and get access to 10+ courses, templates, and a community of 1000+ entrepreneurs—all for less than your daily coffee. 👉

What’s your favorite bundling strategy? Drop a comment below! 🚀

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