The DoubleEdged Sword of AI in Sales Outreach: A Critical Analysis by Will Aitkin


Will Aitkin, a prominent voice in the sales and marketing domain, delves into the growing trend of using generative AI for sales outreach at the AI Revenue Summit 2023. While the allure of automating mass emails is tempting, Aitkin critically examines the potential pitfalls and the importance of human touch in sales communications.

Key Points

1. The Detectability of AI Generated Content: Current AI generated content, especially in emails, is detectable both by AI tools and human readers, undermining its perceived authenticity.
2. The Risk of Spam Filters: Major players like Google and Microsoft, who own Gmail and Outlook respectively, are likely to use advanced tools to filter out AI generated emails, pushing them to spam folders.
3. Human Pattern Recognition: The human brain is adept at recognizing patterns, making it easier for recipients to spot AI generated content after encountering it a few times.
4. The Ethical Implications: Using AI to generate outreach emails can be perceived as deceptive, damaging trust and brand reputation.
5. The Value of Human Touch: Aitkin emphasizes the irreplaceable value of genuine human effort in sales outreach, advocating for a balanced use of AI.

The AI Detection Dilemma 

Aitkin begins by highlighting the ease with which AI generated content can be detected. Using tools like Chat GPT for email generation might seem efficient, but detection tools can often discern AI generated content from human written ones.

The Implications of AI Detection 

Beyond just detection tools, email clients like Gmail and Outlook are constantly evolving their spam filters. Aitkin raises concerns that these platforms might soon prioritize human written content over AI generated emails, affecting deliverability.

The Human Perspective 

While technology evolves, so does human intuition. Aitkin points out that recipients, especially those who receive numerous cold emails, can quickly identify and ignore AI generated content, rendering the outreach ineffective.

Ethics and Authenticity in Sales Outreach 

The ethical dimension of using AI for outreach is profound. Aitkin argues that attempting to automate genuine human interaction can be perceived as insincere, potentially alienating prospects.

The Future of Sales and AI 

While Aitkin acknowledges the potential benefits of AI in sales, such as summarizing lengthy documents or generating ideas, he firmly believes that replacing human effort entirely with AI diminishes the quality of outreach and jeopardizes job security.


Will Aitkin's insights serve as a cautionary tale for sales professionals eager to fully automate their outreach processes. While AI offers numerous advantages, its indiscriminate use, especially in areas requiring genuine human interaction, can be counterproductive. For a deeper understanding of the role of AI in sales and its potential pitfalls, download the event's ebook. Furthermore, consider how "Signals" can complement your outreach strategies, providing insights that can enhance genuine human interactions and drive conversions.