GTM AI Podcast with Coach K and Jonathan Moss

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

Dec 19, 2025
Guest
Anastasiia Ivannikov
Anastasiia Ivannikov, CEO of Folderly and former sales leader at MacPaw, sheds light on the crucial shift in email deliverability following Google's May 2024 switch to AI-based spam detection. She explains how up to one-third of emails now land in spam, discussing the mechanics of spintax and sending velocity to enhance inbox placement. Anastasiia emphasizes the need for human strategy alongside AI tools, advising sales teams to use AI as a thinking partner rather than a crutch, while also advocating for a resurgence of offline outreach methods.
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ADVICE

Fix Reputation, Not Your ESP

  • Use Folderly as an add-on to your sending tool so you keep your current stack while fixing domain and mailbox reputation.
  • Do not switch sending platforms; instead address DNS, warming, and IP/domain health at the infrastructure layer.
INSIGHT

AI Now Judges Email Humanness

  • In May 2024 Google shifted to AI-based spam analysis that judges whether emails 'sound human.'
  • That means AI is now evaluating AI-generated outreach for humanness on the receiving side.
ADVICE

Humanize Copy And Sending Rhythm

  • Use Spintax and varied salutations to create copy variation so Google treats messages as distinct.
  • Space send times in human-like intervals instead of blasting at machine speeds to avoid detection.
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