Upselling sometimes gets a bad rap, but when it's done right, it shouldn't feel like a pushy sales pitch. You're not selling your customer something they don’t need; you're offering more value to people who already trust you.
Whether you sell digital products or event tickets, upselling is one of the simplest and most effective sales techniques for increasing revenue without chasing new customers.
Great upselling strategies guide customers toward the smartest option, so they get more from their purchase, and you boost your average order value in the process.
So, how do you offer better options without sounding pushy? This Checkout Page guide examines 13 effective upselling strategies you should consider implementing.
What is upselling?
Upselling is a sales technique where you recommend a higher-value version of what a customer is already buying. This could look like:
- Upgrading (e.g., VIP ticket instead of general admission)
- Adding on (e.g., a workbook with a course)
- Extending (e.g., annual vs. monthly subscription)
The goal is to boost customer engagement and help them get more value, not just spend more money.
What is the difference between upselling and cross-selling?
Cross-selling involves recommending complementary products or services alongside the original purchase. Instead of encouraging a customer to upgrade, you're helping them expand their experience. For example:
- Buying a course and being offered a 1-on-1 coaching session
- Purchasing design software and adding stock image access
- Signing up for a subscription and getting a deal on a related tool
The key difference? Upselling enhances the original item, while cross-selling adds something new that works with it.
Both aim to increase value for the customer, but from different angles.
💡 Tip: Learn more by reading our guide on upselling and cross-selling
13 Upselling strategies (with examples)
1. Get to know your customer first
Before offering someone more, it’s essential to understand what they want. The best upsells come from insight, not pushing products and hoping for the best.
Start by asking yourself:
- Who is this person, and what are they trying to achieve?
- Are they a first-time buyer looking for a quick win?
- Are they a loyal customer who’s ready for more depth?
- Are they a price-sensitive browser or someone focused on quality?
You can gather this insight through conversation, surveys, site behavior, or purchase history.
Even a simple question like “What brought you here today?” can lead to a more relevant offer.
Why it works: People are far more likely to respond to offers that feel personal and relevant. It builds trust, shows you’re paying attention, and positions you as a guide, not a pushy seller.
Real-world examples:
Event ticketing: “I see you’re attending our marketing conference. Would you like VIP access to the speaker meet-and-greet? It’s perfect for networking.”
This works because it aligns the upsell (VIP access) with the buyer’s likely goal (connecting with speakers or peers).
Digital products: “You downloaded our free SEO guide. Want the full video course with step-by-step case studies and templates?”
In this case, the upsell builds naturally on the user’s interest and offers to take them deeper into the topic they’re already curious about.
2. Personalize the offer
If your upsell sounds like it could be meant for anyone, people are unlikely to feel it is for them. When an offer feels hand-picked, though, it grabs attention.
Personalization doesn’t need to be complex. Use what you know already: their name, plan level, purchase history, or even the page they’re viewing to suggest the next best step. The goal is to make the upsell feel like a logical continuation, not an interruption.
Why it works: Our brains are naturally wired to notice things that feel personally relevant. A “this is for me” moment creates an emotional connection, which drives action.
Real-world examples:
Subscriptions: “Hey [Name], since you’re on our Starter plan, we think you’ll love Pro—unlimited downloads, priority support, and 30+ premium templates.”
You’re acknowledging where they are now and guiding them toward a better version of what they already use.
Event tickets: “You bought a single-day pass. Why not upgrade to the full event and save $50. That way, you won’t miss any of the headline sessions.”
This works because it frames the upsell as a savings and a value boost, plus it reduces regret about missing out.
3. Show clear value (don’t just list features)
When you upsell, don’t just list more features. Explain what those features do for the customer.
“10 extra downloads” doesn’t mean much on its own. “Never run out of content again” paints a picture of ease, speed, or success. Always lead with the outcome, the real-life benefit your customer gets if they say yes to your offer.
Why it works: People make buying decisions based on emotion and justify them with logic. Features are logical, but value is emotional. Customers don’t want products; they want progress, convenience, savings, status, or peace of mind.
Real-world examples:
Digital products: “Upgrade to Pro and cut your editing time in half—most users save 5+ hours a week.”
This connects the dots: what sounds like a feature (advanced tools) is a time-saving mechanism.
Subscriptions: “Go annual and save 20%—that’s like getting 2 months free.”
Framing a percentage as a tangible bonus makes it easier to grasp and say yes to.
4. Justify the price (don’t try and hide it)
Price objections are common, but easier to overcome when you’re upfront and confident. If your upsell costs more, you must show why it’s worth it. Don’t dance around the number; break it down and put it in context.
You can frame the price for cost-per-use, long-term savings, bonuses, or time saved. This helps customers see beyond the number to the value it represents.
Why it works: People don’t mind spending more if they feel they’re getting more. Transparency builds trust, and when the value outweighs the price, it makes much more sense for them to say ‘yes.’
Real-world examples:
Event tickets: “VIP access costs $100 more, including a $150 workshop, complimentary drinks, and front-row seating. You’re saving money while upgrading your experience.”
This reframes the higher price as a net gain, not an extra cost.
Digital products: “The full bundle is $9, but buying everything separately would cost $149. That’s $52 saved, plus bonus templates we don’t sell anywhere else.”
With the upsell, the offer becomes a smarter deal rather than a needless sales push.
5. Add urgency (without being pushy)
Most people will put off a decision until “later,” which often means never.
That’s why giving them a reason to act now is one of the simplest and most effective upselling tools you can use.
Urgency doesn’t have to feel aggressive. It’s about gently reminding customers that the opportunity won’t last forever. You can add pressure respectfully and honestly by using time-limited discounts, expiring bonuses, or low-stock notices.
Why it works: FOMO (fear of missing out) is a powerful psychological trigger. When people feel they might lose access to a better deal or unique benefit, they’re more likely to make a quick decision.
Real-world examples:
Subscriptions: “Prices go up next week! Lock in your current rate before Sunday.”
This gives them a deadline and a clear incentive to act.
Event tickets: “Only 5 VIP spots left—once they’re gone, they’re gone.”
This taps into scarcity and creates immediate motivation, without needing to hard-sell.
6. Bundle related products
Sometimes the best upsell isn’t about upgrading but combining. A well-crafted bundle offers customers more value.
Bundle items that naturally go together. Think tools + training, tickets + recordings, or a main product + support. Offer a small discount on the bundle so it feels like a reward for buying more.
Why it works: People love a good deal, and when you show them they’re getting more for their money, they feel like they’re winning. Bundles also reduce the number of decisions a customer has to make, making it easier for them to say yes.
Real-world examples:
Digital products: “Grab the full creator toolkit: online course + editable templates + 1:1 coaching call. Save 30% when you buy them together.”
This positions the offer as a complete solution, not just more stuff.
Event tickets: “Add a replay pass to your ticket for just $20. You can watch the sessions anytime, even if you miss them live.”
It’s a logical and low-friction add-on that increases value with minimal effort needed from the customer.
7. Make it easy to say yes
Even the most compelling upsell can fall flat on its face if it feels like a hassle.
Complexity kills conversions.
Most people will walk away if there are too many steps, too much risk, or a high upfront cost.
You need to make saying “yes” feel easy and low-stakes. That might mean offering a trial, allowing split payments, or enabling one-click upgrades for returning customers. The fewer barriers between curiosity and commitment, the better.
Why it works: People are more likely to take action when there’s as little friction as possible. You get more conversions when you reduce the mental and financial load of saying yes.
Real-world examples:
Subscriptions: “Try Premium free for 7 days—no credit card required.”
This eliminates the most significant friction points: money and commitment.
Digital products: “Prefer to spread it out? Pay in 3 installments of just $33/month.”
Breaking the price into smaller chunks makes it feel more manageable, especially for higher-ticket items.
8. Let satisfied customers sell for you
Sometimes the best upsell pitch doesn’t come from you but from other customers. When people see others benefiting from the upgrade, their hesitation significantly reduces.
To reinforce trust, use testimonials, star ratings, case studies, or small labels like “most popular” or “best value.”
Why it works: Social proof is one of the strongest psychological motivators. We trust what others say, especially if they’re in our shoes.
Real-world examples:
Event tickets: “92% of VIPs said the upgrade was worth it, especially for the exclusive networking.”
This shows satisfaction and reinforces the specific benefit (networking) the customer likely wants.
Subscriptions: “Over 10,000 users upgraded last month. Why not join the creators who’ve unlocked full access?”
The message? This is the smart move because it’s working for others like you.
9. Use visuals to show the upgrade
Words can tell, but visuals sell. Sometimes, convincing customers of what they're missing is all it takes.
Use simple tools like comparison tables, screenshots, explainer videos, or even before-and-after mockups. Visuals help customers instantly understand the difference between what they have now and what they could get.
Why it works: Our brains process visuals many times faster than text. Showing the value makes it feel more real, which leads to quicker decisions and fewer doubts.
Real-world examples:
Digital products: The “Basic vs. Pro” side-by-side chart shows features like download limits, support levels, and bonus content.
This format makes the upgrade’s value clear at a glance.
Event tickets: Here are photos comparing the VIP lounge (spacious seating, drinks, exclusive access) with the general admission area (standard rows, longer lines).
It turns the upgrade from an abstract benefit into something the buyer can see themselves experiencing.
10. Optimize your checkout flow for upsells
The checkout page isn’t just the finish line. It’s one of the best places in your sales funnel to offer a well-timed upsell because your customer is already in buying mode.
Use in-checkout add-ons, post-purchase one-click offers, or subtle cross-sells that complement their original decision. Keep it simple, relevant, and low-friction.
Why it works: Customers at checkout are mentally prepared to spend. Many will say yes again when you give them a compelling offer with one extra click (and no new form).
Real-world examples:
Digital products: “Before you go, add lifetime access for 50% off. No monthly fees, ever.”
This turns a small upsell into a long-term benefit that feels smart and final.
Subscriptions: “Upgrade to annual now and save $60, plus get a bonus onboarding session.”
You’re bundling savings and value while the customer’s wallet remains open.
11. Follow up after purchase
The sales process doesn’t end at checkout. When someone makes a purchase, they’re in a positive, trusting, and engaged mindset. A thoughtful post-purchase email or thank-you page with a limited-time upsell can turn one sale into another, without the hard sell.
Why it works: People are more open to additional value after buying, especially if it feels exclusive or time-sensitive. This is known as the “buying momentum effect.”
Real-world example:
Digital products: “Thanks for enrolling in the course! Want to go deeper? We are offering the advanced module for 50% off until the end of this month only.”
It rewards the buyer’s action and keeps the momentum going.
12. Reward loyalty
Your most loyal customers are also your warmest leads, so offering them exclusive upsells is a way to say thanks.
Give returning customers something special: early access, loyalty discounts, or invite-only upgrades that feel personal.
Why it works: People love to feel recognized and rewarded. It creates a sense of belonging and boosts lifetime value.
Real-world example:
Subscriptions: “As one of our longtime subscribers, you get 40% off our new productivity add-on—available to members only.”
This upsell is a way of saying thank you to your loyal customers.
13. Use one-click upsells
One of the most effective upselling strategies today is the one-click post-purchase upsell. Right after someone completes their purchase, before they leave the page, offer an irresistible add-on that can be added with a single click.
Platforms like Checkout Page make this easy to implement. It’s seamless, fast, and requires zero re-entry of payment info for your customers.
Why it works: This moment is a psychological ‘sweet spot’ because the initial sale establishes trust, and the customer is in a ‘yes’ mode. If your offer adds value, saying yes to it is as simple as possible.
Real-world example:
Event tickets: “Thanks for grabbing your ticket! Want the full event recordings for just $19? Click once to add it to your order.”
It’s low-risk, high-reward for both the buyer and your business.
How Checkout Page powers upselling
Checkout Page is a no-code checkout builder that helps you turn your checkout into a revenue booster without adding complexity.
Built on Stripe, our platform is designed to help you convert by making it a breeze to upsell, customize pages to match branding, bundle products, offer multiple payment methods, and more.
Here’s how Checkout Page helps you increase sales with upsells, order bumps and more:
✅ Unlimited order bumps at checkout: Offer add-ons like bonus content, recordings, or coaching sessions directly on the checkout page before the customer completes their purchase.
✅ One-click upsells post-purchase: Present relevant upsells after checkout with just one click—the customer does not need to re-enter their card details. This is perfect for offering upgrades, digital bundles, or extended access when conversion likelihood is highest.
✅ Split payments and payment plans: With payment plans and installment options built into the same flow, higher-priced upsells are easier to accept.
✅ Free and paid trials: Let customers try your premium subscription or service before committing, perfect for nurturing upgrades from a basic plan.
✅ Custom billing models: You can design the exact upsell path that fits your business, from one-time payments to subscriptions and tiered pricing.
✅ Dynamic, embedded checkout pages: Place checkout pages anywhere in your sales funnel—on your site, as pop-ups, or embedded in landing pages—so you can upsell in context.
✅ Mobile-optimized and lightning-fast loading: Every upsell experience works seamlessly on any device, making it easy for users to accept offers wherever they are.
✅ Coupon codes, bulk discounts, and time-limited deals: Create urgency with discounts that expire or apply only to bundle deals—ideal for pushing upsells on the spot.
✅ Advanced analytics and conversion tracking: Track how your upsells perform with real-time conversion data, view counts, and UTM tracking.
✅ Custom confirmation pages and redirects: After purchase, show a custom message or send users to an upsell offer with query parameters for personalization.
✅ Supports all major payment methods: Built on Stripe, Checkout Page gives your customers more ways to say yes, including Apple Pay, Google Pay, Klarna, Afterpay, and more.
✅ Integrates with your favorite tools: Sync your upsell offers and customer data with Zapier, Google Sheets, and Rewardful platforms.
With features like these baked into the platform, the Checkout Page doesn’t just process payments; it actively helps you sell more with high-converting pages that can be set up in minutes.
Want to try it out? Start a 7-day free trial—no credit card required—and see how much more your checkout can do for you.
