AI-Powered Cross-Selling: How to Suggest the Right Cannabis Product Every Time

October 5, 2025 /

Cross-selling has always been one of the most powerful tools in retail. Think about when you’re at a coffee shop and they ask, “Would you like a muffin with that latte?” Or when you buy shoes online and the site suggests socks or a cleaner to go with them. These add-on recommendations don’t just increase sales; they also improve the customer experience by making sure people leave with exactly what they need.

In cannabis retail, cross-selling is even more important. Customers often enter dispensaries with limited knowledge, overwhelmed by menus filled with flower, edibles, vapes, tinctures, topical, and accessories. A smart, helpful suggestion can turn a single purchase into a complete experience—boosting both customer satisfaction and revenue.

The real hurdle lies in consistently delivering the most relevant recommendation. That’s where Artificial Intelligence (AI) comes in. AI-powered cross-selling is transforming cannabis marketing and sales by helping dispensaries suggest the perfect product at the perfect moment.

In this blog, we’ll explore what AI-powered cross-selling is, why it’s a game-changer for cannabis businesses, and how dispensaries can use it to drive sales and build customer loyalty.

What is Cross-Selling in Cannabis?

Cross-selling is the practice of suggesting complementary products to customers based on what they’re already buying. In cannabis, it looks like this:

  • Customer buys flower → Suggest rolling papers, lighters, or grinders.
  • Customer buys gummies → Suggest chocolates or drinks for variety.
  • Customer buys a vape pen → Suggest extra cartridges or cleaning tools.
  • Customer buys CBD tincture → Suggest topical creams for targeted relief.

Cross-selling works because it solves problems customers haven’t thought about yet. Instead of just selling a product, you’re creating a better experience.

Why AI Makes Cross-Selling Smarter

Traditional cross-selling relies on human budtenders or static “Frequently Bought Together” lists. But these methods are limited. Budtenders can’t memorize every possible pairing for every customer, and generic suggestions often miss the mark.

AI changes that by personalizing recommendations in real time. Here’s how:

  1. Data-Driven Insights

AI analyzes past purchases, browsing behavior, and customer preferences.

  • Example: If a customer usually buys sativas and carts, AI might recommend a new citrus-flavored vape cartridge instead of a random indica.
  1. Customer Segmentation

AI automatically groups customers into segments—like “edible enthusiasts,” “wellness-focused buyers,” or “flower purists.” Each group gets tailored cross-sell suggestions.

  1. Real-Time Recommendations

Instead of static product bundles, AI responds to customer behavior instantly.

  • Example: Someone adds a vape pen to their cart → AI instantly recommends the most popular cartridges that fit that pen.
  1. Omnichannel Consistency

AI-powered cross-selling works across in-store kiosks, websites, mobile apps, and even text or email campaigns. Wherever your customer shops, they see consistent, relevant suggestions.

  1. Continuous Learning

AI improves over time. The more customers interact with recommendations, the smarter the system gets at predicting what works.

Benefits of AI-Powered Cross-Selling in Cannabis

Implementing AI-powered cross-selling isn’t just about making more money (though it does that too). It’s about building better customer experiences. Here’s why it’s a win-win:

  1. Increased Sales per Customer

AI suggests products customers actually want—so they’re more likely to buy them. This increases average order value (AOV) without feeling pushy.

  1. Better Customer Satisfaction

When recommendations feel personalized, customers feel understood. Instead of generic upselling, they see relevant suggestions that enhance their purchase.

  1. Education through Suggestions

Cannabis is still confusing for many buyers. AI recommendations double as education.

  • Example: A first-time vape buyer might not know they need a cartridge. AI makes sure they don’t walk out with an incomplete purchase.
  1. Improved Inventory Turnover

AI can help move slow-selling items by suggesting them to the right audience. Instead of discounts, cross-selling gets products into the hands of customers most likely to enjoy them.

  1. Consistency across Channels

Unlike budtenders (who vary in skill), AI provides consistent, data-backed suggestions—whether a customer shops online or in person.

Examples of AI Cross-Selling in Cannabis

Let’s bring this to life with real-world cannabis scenarios.

Example 1: The Edible Explorer

  • Customer adds a 10mg THC gummy pack to their cart.
  • AI suggests:
    • A CBD tincture for balance
    • A chocolate edible for variety
    • A “snack bundle” deal with drinks and gummies

Result: Customer walks away with 3 products instead of 1.

Example 2: The Vape Enthusiast

  • Customer buys a vape battery.
  • AI suggests:
    • Top-selling cartridges compatible with the battery
    • A cleaning kit for maintenance
    • A disposable pen for on-the-go use

Result: Customer discovers accessories they didn’t know they needed.

Example 3: The Wellness Seeker

  • Customer buys CBD capsules.
  • AI suggests:
    • A topical balm for sore muscles
    • A CBN tincture for sleep support
    • A loyalty program sign-up for wellness-focused deals

Result: The brand becomes a trusted wellness partner, not just a store.

How AI Cross-Selling Works Step by Step

Let’s break down the process:

  1. Data Collection
    • AI gathers customer data: past purchases, browsing history, demographic info.
  2. Pattern Recognition
    • AI identifies relationships between products customers often buy together.
  3. Segmentation
    • Customers are grouped into segments based on behavior.
  4. Real-Time Decisioning
    • When a customer adds an item to their cart (online or in-store), AI instantly analyzes what else they might want.
  5. Recommendation Delivery
    • Suggestions appear on:
      • In-store tablets
      • Online product pages
      • Checkout screens
      • Post-purchase emails
  6. Feedback Loop
    • AI measures which suggestions customers accept or ignore, improving future accuracy.

Overcoming Challenges in AI Cross-Selling

Like any technology, AI-powered cross-selling comes with challenges. Here’s how to handle them:

  1. Regulatory Compliance
    • Cannabis advertising rules vary by state. AI must filter recommendations to stay compliant.
  2. Data Privacy
    • Customers may worry about data use. Be transparent about how their data improves their shopping experience.
  3. Integration Costs
    • AI platforms require investment. Start small—many affordable AI plugins exist for e-commerce and POS systems.
  4. Maintaining the Human Touch
    • AI should assist, not replace, budtenders. The best cross-selling combines AI recommendations with human interaction.

The Future of AI in Cannabis Cross-Selling

The potential of AI goes beyond today’s recommendation engines. Here’s what’s next:

  • Voice-Powered Recommendations
    • Customers using Alexa or Siri could hear product suggestions instantly.
  • Augmented Reality Shopping
    • Imagine customers scanning a product with their phone and seeing AI-driven “pair it with this” suggestions in AR.
  • Predictive Reordering
    • AI could predict when customers will run out of a product and send reminders or offers before they do.
  • Emotion AI
    • Recommendations could adapt to customer mood, using tone of voice or facial recognition.

Why AI Cross-Selling is a Must for Cannabis Brands

Cannabis is a unique market. Customers want education, variety, and convenience—but they don’t always know where to start. AI-powered cross-selling bridges that gap.

For dispensaries, this means:

  • Higher revenue per transaction
  • Smarter inventory management
  • Better customer loyalty
  • Differentiation in a competitive market

For customers, it means:

  • No forgotten accessories
  • Personalized, educational shopping
  • A smoother, more enjoyable buying experience

It’s not just about selling more—it’s about selling smarter.

How Highly Marketable Helps You Cross-Sell Smarter

At Highly Marketable, we specialize in helping cannabis businesses harness AI for growth. Our AI-powered cross-selling strategies help you:

  • Build personalized product recommendations
  • Automate cross-sell suggestions across channels
  • Stay compliant with cannabis advertising rules
  • Improve customer satisfaction and loyalty
  • Turn one-time sales into long-term relationships

We don’t just increase your average order value—we help you create smarter shopping journeys that keep customers coming back.

Final Thoughts

Cross-selling is one of the oldest tricks in retail, but AI makes it smarter, faster, and more effective than ever before. For cannabis businesses, this means more than boosting sales—it means becoming a trusted guide for customers navigating an often overwhelming industry.

By suggesting the right product at the right time, AI ensures your customers leave happy and come back for more. And in a competitive cannabis market, that’s the kind of edge you can’t afford to ignore.

If you’re ready to take your cannabis sales strategy to the next level, it’s time to embrace AI-powered cross-selling. Because the right suggestion, delivered at the right moment, can make all the difference.