Use AI to Write Upsell Emails that Work (with Prompts)

marketer using AI to write upsell emails

In the fast-paced marketing world, crafting effective emails is crucial for boosting revenue and customer loyalty. Here is our expert guide with AI-powered prompts, FAQs, and best practices to help experienced marketing managers like you boost revenue and customer lifetime value through effective upsell email campaigns.

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First, Generate Your Marketing Overview

Paste the following prompt into ChatGPT or a similar AI tool:

Hello! I’m a busy marketing manager who wants to create a concise marketing overview for my business. I need your assistance in this process. Please ask the following ten questions, one at a time.– What is the name of your business?

– Please provide a link to your website.

– What industry does your business operate in?

– What products or services does your business offer?

– Who is your target audience or customer base?

– What is their pain point?

– What is the unique value proposition or key differentiator of your business?

– How long has your business been operating?

– What are the main goals and objectives of your business?

– Are there any specific marketing channels or strategies that you have used in the past?

Based on my answers, please generate a marketing overview to serve as a primer for future AI prompts. Leverage the 24 VIA character strengths where appropriate. Then, let’s check the marketing overview for accuracy, asking any clarifying follow-up questions if needed.

Then, Generate Your Upsell Emails

In the same chat session, paste the following prompt:

Based on this marketing overview, I want to create upsell emails for my business. Please ask the following questions, one at a time, allowing me to skip questions I don’t know.

  • Which specific products or services are you interested in upselling via email marketing?
  • What are the current product or service offerings that you want to use as a foundation for upselling?
  • What customer behaviors trigger upsell emails in your CRM system (purchases, membership milestones, etc.)?
  • How do these products offer increased customer value?
  • Could you provide data on your historical upselling efforts, including conversion rates or customer feedback?
  • Do you have any specific creative ideas or messaging themes for your upselling emails?

Based on my answers, please generate a draft upsell email. Leverage the 24 VIA character strengths where appropriate. Then, let’s check the upsell emails for accuracy, asking any clarifying follow-up questions if needed.

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More AI Prompts for Writing Upsell Email Examples

The best results in creating compelling and personalized upsell email messages come from combining AI expertise and human creativity. Here are some prompts you can use with a tool like ChatGPT to refine your upsell email examples:

  • Personalize product recommendations: “Suggest personalized product recommendations based on the customer’s <behavior>.”
  • Optimize subject lines: “Generate attention-grabbing subject lines to increase my <open rate/CTR/conversion rate>.”
  • Craft persuasive CTAs: “Create compelling calls to action that drive customers to explore upsell options.”
  • Explain value succinctly: “Write concise descriptions that convey the value of my upsell products or services.” [Insert product details]
  • Address objections: “Generate responses to common customer objections to address concerns preemptively.”
  • Highlight benefits: “Emphasize the benefits of bundling or persuasively adding complementary items.”
  • Leverage social proof: “Incorporate social proof, such as reviews or testimonials, to build trust and credibility.”
  • Create urgency: “Craft time-limited offers or incentives to motivate prompt action.”
  • Segment your audience: “Help segment my customer list based on [persona criteria] for targeted upsell campaigns based on [behaviors].”
  • A/B testing ideas: “Provide suggestions for A/B testing [design or content element].”

10 Best Practices for Writing Upsell Emails That Work

  • Segment Your Audience: Divide your customer list to tailor upsell emails to specific buyer personas.
  • Leverage Customer Data: Use purchase history and behavior to recommend relevant upsell products that speak to the needs of your customers.
  • Create Persuasive Subject Lines: Craft compelling subject lines to increase email open rates.
  • Highlight Value: Communicate the unique benefits of the upsell in concise terms that build from any original offers and customer pain points.
  • Showcase Social Proof: Incorporate reviews or testimonials to build trust and credibility for upsold products.
  • Craft Irresistible CTAs: Create compelling calls to action that encourage customers to take action.
  • Offer Time-Based Incentives: Provide upsell offers based on a time limit. This can increase urgency with customers, which might push them into making a more immediate decision.
  • Personalize and Humanize: Make emails feel personal and human, not overly automated. Address customers by name and use insights gained from research to speak directly to pain points and needs.
  • Optimize for Mobile: Ensure your emails are mobile-responsive for a seamless user experience.
  • Monitor and Iterate: Continuously track the success of your upsell emails and make improvements based on data and feedback.

Female marketer glad to work with AI for email writing

Frequently Asked Questions (FAQs) About Writing Upsell Emails


What are upsell emails, and why are they important for my business?

Upsell emails are messages designed to encourage existing customers to purchase additional or higher-value products or services. They're important as they can significantly boost revenue and customer lifetime value.


How can I effectively segment my email list for upsell campaigns?

Segment your list based on purchase history, behavior, or demographics to send targeted, relevant upsell offers.


What's the ideal frequency for sending upsell emails?

Upsell emails often coincide with customer actions, so your mileage may vary in frequency. Typically, it’s a good idea to send emails after a customer purchase, during a product launch, and when customers pass a particular milestone (such as member points earned or money spent on a single order).


What types of incentives work best for upselling emails?

Incentives like exclusive discounts, limited-time offers, or bundled savings are effective in driving upsell conversions.


How do I create compelling subject lines for upsell emails?

Craft subject lines that highlight the value or benefits of the upsell based on the behavior and persona of the customer. This subject should speak directly to that behavior and what they might respond to.


Is it a good idea to use social proof in upsell emails, and how?

Yes, social proof like customer reviews or testimonials can build trust and show the value of the upsell.


How can I make upsell emails more personal and relevant to customers?

Use customer data to recommend upsell products that align with their preferences and past behavior.


Should I automate my upsell email campaigns or send them manually?

A mix can work well; automate when appropriate, but personalize and manually craft some emails for a human touch.


How do I measure the success of my upsell email campaigns?

Track metrics like conversion rates, revenue generated, and customer feedback to evaluate the effectiveness of your upsell email strategy.


10 Protips for Writing Cross-Sell Email Examples

  1. Segment Customers: Know Your Audience. Segment your customer list to send cross-sell offers tailored to specific buyer personas.
  2. Bundle Products: Bundle Complementary Items. Create bundled offers to make cross-selling more appealing and valuable for customers.
  3. Create Urgency and Scarcity: Create FOMO. Use limited-time offers or limited stock notifications to encourage prompt action in your cross-sell emails.
  4. Showcase Trust: Show Trustworthiness. Incorporate customer reviews and testimonials to build trust and credibility in your cross-sell messages.
  5. Craft Clear CTAs: Guide Action. Craft clear and compelling calls to action that prompt customers to explore cross-sell options.
  6. Educate with Content: Inform and Engage. Provide informative content in your emails that helps customers understand the value of cross-selling items.
  7. Test and Refine: Refine Your Strategy. Regularly test elements like email design, copy, and product placement to optimize cross-sell email performance.
  8. Leverage Data Insights:  Leverage Analytics. Analyze data to understand customer behavior and preferences for better cross-selling.
  9. Observe Timing and Frequency: Be Strategic. Determine the best times to send cross-sell emails and strike the right balance in frequency.
  10. Optimize for Mobile: Go Responsive. Ensure your cross-sell emails are mobile-friendly for a seamless user experience, as many customers use mobile devices for email.

Unlock the full potential of your email marketing strategy – Media Shower’s AI and content specialists will take your upsell campaigns to the next level. Get started today for higher engagement and profits.