Raphael BenhamouMember of the Board of Advisors, Boardy · Fractional CFO for $5M+ companies in transition

AI Email Personalization Backfires

4 May 2026 · 1 min

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1:05

An email automation platform got crushed when Gmail started catching AI-written messages. The flood of cold emails tanked their reputation, and the AI couldn't match users' actual voices, forcing them to manually fix everything.

Chapters

Right? Because here I was writing all these hyper-personalized emails. And actually what happened with AI and the big surprise was that it started hurting the technology that I just invested years building because everybody was starting to personalize their emails using AI. Gmail and all the other platforms started getting smart at detecting AI-written emails. And so this whole platform and everybody started sending more cold emails because it was so easy to write them. Yeah. Right? So it actually caused major harm to the whole platform that I built. And so that was really a huge setback. How did you overcome that? So we actually, and also I'll tell you another setback was that with AI, everybody has their own tone. Everybody has their own way of writing. And you can train the AI, definitely, but it takes time. And when users would log in and have it run, they were like, I don't sound like that. So we would say, okay, edit the message, teach it how you, you know, your tone, your style, tell it to remove these words.