Humanizing outreach with Spintax and spacing

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YouTube Description

Google's AI Is Judging Your AI: The Email Deliverability Wake-Up Call Every Sales Team Is Missing

Every third email you send lands in spam. That's 40-50% of your pipeline that never even sees your outreach.

In May 2024, Google quietly switched to AI-based spam detection. Not keyword filters. Not rule-based systems. Actual AI deciding whether your AI-written emails sound human enough to reach an inbox.

Most sales teams have no idea this happened. They're still running the same playbook while their domain reputation burns.

Anastasiia Ivannikov, CEO of Folderly and former sales leader at unicorn Macpaw, breaks down exactly what changed and what to do about it. We get into the mechanics—spintax, sending velocity, behavioral signals—and the bigger strategic problem: teams using AI as a brain replacement instead of a thinking partner.

If you're running outbound, managing SDRs, or building AI-powered GTM motions, this one's required listening.

TIMESTAMPS

0:00 - Intro 1:00 - Anastasiia's background (started in sales at 14, joined Folderly with a 3-week-old baby) 3:00 - The problem: every third email lands in spam 5:00 - Cold outreach vs email marketing—same problem, different mechanics 7:00 - How Folderly works with AI SDRs and automation tools 8:00 - Is email dead? (Spoiler: no, but it's changing) 10:00 - The data: what actually impacts deliverability 11:00 - Google's AI shift in May 2024—AI judging AI on humanness 12:00 - Spintax explained: why copy variation is now survival mechanics 13:00 - Sending velocity: why your sequencing tool's defaults are killing you 14:00 - Value-based email content vs lazy blasting 15:00 - AI as thinking partner vs AI as brain replacement 17:00 - Why single-LLM dependency creates strategic blind spots 18:00 - The future of Folderly and multichannel outreach 19:00 - The new math: 5 touches to convert → now 17 21:00 - Why offline and physical channels are making a comeback 22:00 - Detecting AI content (the M-dash and "fluff" triggers) 23:00 - What Anastasiia's excited about: smaller teams, faster MVPs 26:00 - The value of human oversight when AI does 95% of the work 28:00 - Prompting still matters even as models improve 29:00 - Anastasiia's AI tool stack: Gamma, Midjourney, Clay, n8n, Instantly, Descript

KEY TAKEAWAYS

→ Google switched to AI-based spam detection in May 2024 → Spintax variations are no longer optional—they're table stakes → Sending velocity matters as much as copy quality → Use multiple LLMs to avoid strategic blind spots → 17 touches to convert now vs 5 a few years ago

CONNECT

Anastasiia Ivannikov: https://www.linkedin.com/in/anastasiia-ivannikova/ Folderly: https://folderly.com

Coach K (Jonathan Kvarfordt): https://www.linkedin.com/in/jonathankvarfordt/

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Drop a comment: What's your current email deliverability rate? Most teams don't even know