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Cross-Sell and Upsell Messaging

use this prompt when:

  • You need to create strategic follow-up messaging for existing customers who have already purchased your core product
  • You’re launching complementary products or premium tiers that enhance your customers’ initial purchase
  • You want to increase customer lifetime value without appearing pushy or solely transaction-focused
  • You need to optimize messaging across various customer touchpoints (email, in-app, packaging inserts, etc.)
  • You’re refining your post-purchase customer journey to incorporate relevant opportunities for additional value

The prompt

Develop cross-sell and upsell messaging for customers who have purchased <primary product/service> to encourage them to consider <complementary or premium offerings>. Create <number> message variations using different approaches (logical extension, enhanced value, problem expansion, etc.) that feel helpful rather than pushy. For each message, highlight the incremental benefit of <incremental benefit>, address the hesitation of <common hesitation>, and incorporate the relationship context. Include placement recommendations for these messages across <customer touchpoints> and timing guidance based on the customer lifecycle stage of <lifecycle stage>.

How to customize

Cross-Sell and Upsell Messaging
Variables
Description
Variables
primary product/service
Description
Specify the core product or service that customers have already purchased (e.g., "skincare starter kit," "basic subscription tier").
Variables
complementary or premium offerings
Description
List the specific products, services, or upgrades you want to promote to existing customers (e.g., "premium moisturizer," "annual membership," "personalized consultation").
Variables
number
Description
Determine how many message variations you need (typically 3-7 works well to test different approaches).
Variables
incremental benefit
Description
Identify the specific additional value customers will gain from the cross-sell/upsell (e.g., "30% more effective results," "save 4 hours weekly," "exclusive content access").
Variables
common hesitation
Description
Note the typical objection or concern customers have about purchasing additional items (e.g., "price sensitivity," "product overload," "commitment concerns").
Variables
customer touchpoints
Description
Specify where these messages will appear (e.g., "order confirmation emails, product packaging, account dashboard, SMS").
Variables
lifecycle stage
Description
Indicate when in the customer journey these messages should appear (e.g., "2 weeks post-purchase," "after 3rd use," "subscription renewal window").

Example Output

Cross-Sell and Upsell Message Strategy for GLOW Natural Skincare

 

Product Context:
Primary Product: GLOW Daily Essentials Kit (cleanser, toner, moisturizer)
Complementary Offerings: Weekly Enzyme Mask, Overnight Recovery Serum
Customer Segment: First-time purchasers, 25-45 age range

 

Message Variations:

  1. Problem Expansion Approach
    Message: “Loving your daily GLOW routine? Many customers tell us that while their everyday skin looks refreshed, they still struggle with occasional dullness. Our Weekly Enzyme Mask works with your Daily Essentials to gently remove buildup that regular cleansing can’t reach, revealing your skin’s natural radiance without harsh scrubbing. It’s like giving your skincare routine a power boost once a week.”
    Incremental Benefit Highlight: Addresses skin concerns that daily care alone can’t solve (40% brighter skin appearance after first use)
    Hesitation Addressed: “I already have enough products” → Positions as occasional supplement, not daily commitment
    Placement: Product insert card, 2 weeks post-purchase email
    Timing: After customer has established daily routine (approximately 14 days post-purchase)
  2. Enhanced Value Approach
    Message: “Your GLOW Daily Essentials are building a strong foundation for healthy skin. Ready to maximize those results? Our Overnight Recovery Serum works while you sleep – when skin does its best repair work – to enhance the effects of your daily routine by up to 60%. The potent antioxidants complement your moisturizer perfectly, for visibly refreshed skin each morning.”
    Incremental Benefit Highlight: Accelerated results from existing routine (60% enhanced effectiveness)
    Hesitation Addressed: “Is it worth the extra cost?” → Emphasizes amplifying value of current investment
    Placement: Follow-up email sequence, replenishment reminder
    Timing: 3-4 weeks after purchase, when customers are seeing initial results from daily routine
  3. Logical Extension Approach
    Message: “Did you know? 92% of GLOW customers who add our Overnight Recovery Serum to their Daily Essentials routine report seeing twice the improvement in skin texture in half the time. It’s the natural next step once you’ve established your daily basics. Plus, using them together means each product lasts longer – just 2-3 drops of serum boosts your moisturizer’s effectiveness significantly.”
    Incremental Benefit Highlight: Faster results, extended product life
    Hesitation Addressed: “My routine is already complicated enough” → Presents as simplified path to better results
    Placement: Account dashboard “recommended for you” section, bottom of digital receipt
    Timing: At first repurchase consideration point (approximately 6-7 weeks post-purchase)
  4. Social Proof Approach
    Message: “Welcome to the GLOW community! We noticed you’re loving your Daily Essentials Kit. 78% of customers like you enhance their routine with our Weekly Enzyme Mask after about a month of use. ‘It’s the perfect complement to my daily routine – gives my skin that extra boost when I need it most,’ says Maya, a GLOW customer since 2023. Ready to experience the full GLOW effect?”
    Incremental Benefit Highlight: Community-validated enhancement
    Hesitation Addressed: “Not sure if I’ll see additional benefits” → Uses peer experiences to build confidence
    Placement: SMS message, packaging insert with QR code to customer testimonials
    Timing: 30 days post-purchase, when seeking community validation becomes important

 

Placement Strategy Across Customer Journey:

  • Initial unboxing: Include small sample of complementary product with elegant card explaining how it enhances the routine
  • Post-purchase email sequence: Introduce complementary products gradually, starting with education before offering purchase options
  • Social channels: Share before/after content from customers using the complete system vs. basics only
  • Replenishment moment: Bundle offer with small discount when purchasing refills of original products

 

Recommendation: Start with the Problem Expansion approach during the 2-week post-purchase window, when customers have established their routine but may be noticing limitations. This timing acknowledges their commitment to the base product while naturally introducing how complementary offerings address needs the basic routine wasn’t designed to solve.

Pro tips

Cross-Sell and Upsell Messaging
  • Always lead with educational content about the complementary product benefits before presenting the sales message – this builds trust and demonstrates customer-centricity
  • Create visual content showing how products work together in a system for maximum effect (infographics or simple routine diagrams)
  • Test both timing and message approach variables separately to identify the ideal combination for your specific customer base
  • Consider creating tiered incentives that increase in value the longer a customer waits to purchase, which creates urgency without appearing desperate

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