An experiment in AI copywriting

Following Ross Simmonds' lead... Ross is a Canadian marketer and content agency owner who's making a name for himself (and his agency) in Eastern Canada. He freely shares insights and learnings online. Recently, he'd been sharing good/bad AI prompts.

The prompt: You're a blend between two of the best email copywriters ever, Joanna Wiebe and Luciano Viterale. You've been tasked with writing an email drip campaign that gets sent when someone downloads an ebook titled [TOPIC]. Use their first principles when crafting this sequence of emails and strive to convert website owners who downloaded it into a [COMPANY] customer.

- Ross Simmonds


Never one to shy away from a helpful tip, I did just that. I chose one of our most important offers, 12 Questions Your prospects are Asking, Whether They Know it or Not, and ran it through ChatGPT using his prompt. This is what it produced:


Unlock the Deeper Questions Your Prospects are Asking

Learn the 12 Questions Behind What Truly Drives Your Audience to Act or Not

Welcome to a new perspective in understanding your prospects. Beyond the surface-level "What's in it for me?" lies a realm of deeper, more impactful questions. In our ebook, "Unlock the Deeper Questions...," we uncover the psychology that truly influences their decision-making.

What Awaits Inside:

  1. Beyond the Surface: Learn to recognize the unspoken concerns and aspirations driving your audience.
  2. Trust and Integrity: How to build credibility and foster trust with your prospects.
  3. Understanding Needs: A dive into how perceptions, identity, and self-image shape customer decisions.
  4. Actionable Insights: Practical strategies to address these deeper questions and positively influence buyer behavior.

For Whom? Website owners, marketers, and entrepreneurs seeking to connect more profoundly with their audience and drive meaningful engagement.

Take the First Step: Download the ebook and begin the journey to truly understanding your prospects. Equip yourself with the knowledge to not just ask the right questions, but to provide the answers your audience seeks.

Why Kayak Marketing? We're not just about digital strategies; we're about understanding the human elements behind every click and conversion. With a blend of psychological insight and marketing expertise, we guide our clients to not just meet, but exceed their audience's deepest needs.

Ready to Deepen Your Marketing Approach?
[Download Now Button]


Images generated by ChatGPT's DALL-E based on the same prompt.


Email 1: Introduction to Deeper Insights

  • Subject Line: Going Beyond "What's in it for me?" Uncovering What Your Prospects Really Think
  • Content guidance: Introduce the deeper level of questions prospects ask, based on the ebook. Highlight how Kayak Marketing helps in understanding and addressing these complex queries.

Email 2: Delving into Prospect Psychology

  • Subject Line: The Psychology Behind Your Prospects' Choices
  • Content guidance: Discuss the importance of understanding the psychological aspects driving customer decisions, as outlined in the ebook. Relate this to how Kayak Marketing's approach is tailored to these insights.

Email 3: Trust and Credibility

  • Subject Line: Building Trust and Credibility with Your Audience
  • Content guidance: Focus on the importance of trust and integrity in customer relationships. Explain how Kayak Marketing's strategies help in fostering this trust.

Email 4: Addressing Deeper Concerns

  • Subject Line: Answering the Unasked Questions of Your Prospects
  • Content guidance: Discuss how Kayak Marketing helps in identifying and addressing the deeper, often unasked questions that prospects have, as mentioned in the ebook.

Email 5: Driving Decisions and Action

  • Subject Line: Guiding Prospects to Positive Decisions
  • Content guidance: Highlight how understanding deeper psychological triggers, as detailed in the ebook, can lead to more effective marketing strategies with Kayak Marketing.

Email 6: The Path to Enhanced Engagement

  • Subject Line: Transform Your Engagement with Deeper Insights
  • Content guidance: Conclude by emphasizing the importance of deeper customer understanding for effective engagement, inviting the reader to explore Kayak Marketing's services for achieving this.

What do you think?

Did ChatGPT live up to the prompt Ross created?

Landing Page rationale: In this copy, the focus is on encouraging website owners to delve deeper into understanding their prospects, positioning the ebook as a valuable resource for gaining this insight. The content aims to intrigue the reader, highlight the unique approach of Kayak Marketing, and prompt action through a clear call-to-action.

Email Series rationale: Each email in the series focuses on the psychological and deeper motivational aspects of customer behaviour, aligning closely with the content of the blog post and ebook. This approach aims to engage the reader on a more intellectual level, fostering a deeper understanding of the complex dynamics of customer engagement.

If you're curious about the eBook, check it out below.


unlock deeper questions