Strategies For Upselling During Checkout

Our platform processed $225 million in upsell revenue last year, and 90% of it came from just TWO types of upsells. Most businesses are overcomplicating this, costing themselves millions. The highest-converting upsell types aren't complex: 1. MORE OF WHAT THEY JUST BOUGHT This is the Costco principle: • Selling dance classes? Upsell more classes • Selling supplements? Upsell more bottles • Selling monthly subscriptions? Upsell annual plans They've already made the psychological commitment to the product. You're not asking for a new decision, just extending the existing one. 2. FASTER/EASIER IMPLEMENTATION This removes friction between purchase and benefit: • IKEA sells furniture → Upsells assembly service • Course creator sells program → Upsells done-for-you templates • Software company sells platform → Upsells setup service Customers buy for the end result, not the product itself. This gets them there with less pain and time investment. The CRITICAL MISTAKE killing your upsell conversions is treating your new customer like they're not yet a customer. This looks like: "Hey, I also have this other thing you should buy..." Instead, acknowledge their purchase FIRST: "Congratulations on your decision! You're going to love [product they just bought]. Before you get started, many customers like you asked for [specific benefit], so I created this to help..." This subtle shift creates: → Validation of their initial purchase → A natural bridge to the next offer → A customer-centric reason for the upsell The biggest upsell danger is making customers feel their initial purchase was incomplete. Every upsell should enhance the core product, never make it feel insufficient. Master these two upsell types and the proper positioning, and you'll capture the revenue most businesses leave on the table.

A lot of brands' checkout flow kind of comes off like a used car salesman. "Buy more!" "Don't leave!" "Last chance!" I get it. You've worked hard (and spent a lot) to get that customer there. But here's what we learned at Obvi this year - your checkout flow should act more like a trusted advisor than a pushy sales rep. Think about it: The customer is already interested. They've added something to cart. Now they're looking for validation, education, and maybe a little reward for taking the plunge. At this moment, you have 2 paths: - You can hammer them with aggressive upsells and urgency... - Or you can guide them toward the best possible experience with your brand. We figured out how to build path 2, and it changed everything. Here's how we think about it →  First, we educate. Our checkout shows relevant reviews that speak to specific results and experiences. Not just "great product!" but real stories from our 250,000+ customers about their journey. Next, we validate.  Every product in-cart gets paired with our guarantee, FDA certification, and "Made in USA" badges. But we also explain WHY these matter for supplements. Trust isn't just about logos - it's about context. Then we reward smart choices.  Instead of just offering random bundles, we show volume discounts that actually make sense. "Get 3 months supply, save 20%" hits different when you've just read reviews from people talking about their 90-day transformations. The results have been eye-opening 👀 - Higher AOV (because people are choosing bundles that fit their goals) - Better retention (because they're starting with the right products) - Fewer support tickets (because we're answering key questions up front) But the biggest win? People are actually excited about spending more with us. The checkout isn't friction - it's part of their journey to better health. You CAN use scarcity and urgency and all that kind of stuff to up purchase intent. But you have to do it right. AfterSell by Rokt has been crucial for testing and optimizing all of this for us. Remember: Your checkout flow isn't just about moving product. It's about helping the customer buy the right stuff for them and building the foundation for a long-term relationship. Educate. Validate. Reward. Make it helpful, not pushy.  Guide, don't grind.

I said this in a webinar recently: The name of the game in DTC is  “whoever can afford the highest CAC will survive.” But to do that, you need a high AOV, a sticky subscription program, or a lot of cash in the bank. We went with focusing on increasing order value. Here are 4 of my favorite ways we’ve found to ⬆️AOV so far… 1. Upsell "more of the same" - Instead of upselling something new, we offer more of the same product the customer with a volume discount. This approach has increased our take rate SIGNIFICANTLY without hurting conversion. Why it works: The customer is already invested in the product - they’ve learned about it through ads, LPs, etc. So we just tap into their existing commitment, making the offer more enticing. 2. Urgency & Scarcity During the purchase flow, we highlight messages like "This product sells out fast" or "For best results, use for 8–12 weeks.” You can also try things like countdown timers and “low inventory” messaging to really drive this home. Why it works: Customers at the bottom of the funnel can be motivated by FOMO —they don’t want to miss out on getting the deal you’re offering, especially one they perceive as beneficial. If a product might sell out soon or if buying more now means they won’t run out later, they’re more likely to purchase right away or more of it. 3. Sequential Offers After someone buys from us, our post-purchase funnel begins immediately with our volume discount upsell. If they skip that, Obvi presents them our cross-sell and down-sell offers in a sequential funnel: First → Volume/bulk discount upsell Second → Complementary product offer Third → Smaller accessory or branded gear Why it works: This structured approach helps avoid overwhelming the customer with too many offers at once. Each step is designed to maximize potential revenue (highest-performing upsell shown first) while maintaining a logical flow. 4. Maximize the Thank You Page This is a simple one that a lot of brands miss.  Your thank you page has a bunch of valuable real estate that every one of your buyers look at it. At Obvi, we maximize this with post-purchase surveys and network offers. Network offers are a complete no-brainer for us. Big brands like Nike and Hulu pay to present offers to our customers on our Thank You page. If a customer opts in, we get some $. Why it works: It’s a win-win-win. The customer gets a good deal, the big brand gets another subscriber, and the seller gets incremental profit. For Obvi, it has resulted in about +$0.45 more per transaction so far. Post-purchase surveys won’t directly add $ to your bottom line, but they give you valuable insights about customer behavior and perceptions. Not to mention marketing attribution. That’s it, you know our ⬆️AOV secrets. BTW, AfterSell by Rokt is the tool we’ve used to test and execute these tactics. If you’re a Shopify brand looking to grow your AOV without hurting your conversion rate, they can help you get there.