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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

KEY TAKEAWAYS

→ Google switched to AI-based spam detection in May 2024

CONNECT

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

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

SUBSCRIBE for weekly conversations with GTM leaders on AI, sales, and revenue operations.

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

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Ghost Team co-founder Elliot Garreffa breaks down why most companies struggle to see ROI from AI—and what to do about it. This conversation cuts through the hype to reveal the unglamorous truth: successful AI implementation isn’t about buying licenses or running proofs of concept. It’s about understanding your actual workflows, identifying where AI creates 10x (not 2x) improvements, and building systems that your teams will actually use. Elliot shares real examples of SEO systems that compress months of agency work into minutes, and explains why human-in-the-loop isn’t a compromise—it’s best practice.

“If you just go and prompt an LLM and try to create some content, it might make incremental improvements, but it’s actually not that good. Where we come in is building systems that create 10x, 100x improvements.”

“You have to really understand the problem before you tackle it. Any good technology implementation does that step upfront, and we’ve found it incredibly true for the AI space.”

“Don’t think about using AI to do this part of this process. You can just do an entirely different process. That gets far better results than just slapping things on top.”

“The kind of thing that would’ve taken months to get back from an agency—we’re doing it directly within the chat window. That obviously changes a lot in terms of a typical process.”

“When you add that human touch, it is significantly better. Regardless of how much training data you have, you can still really tell whether something has been AI-generated or not.”

“One of the best things you can do when first getting started: look at things you’re spending a huge amount of time on. Focus on automating those first. They save you time, which means you can focus on more valuable tasks.”

“People see these workflow automations on LinkedIn and they want them. But whether these systems work is all about the detail under the hood—the prompting, the training data, the customization to your brand.”

This conversation goes deep on MCPs, context engineering, and the technical stack that actually delivers results. Listen to the full episode to hear Elliot walk through a live demo of automated SEO research and strategy that would take traditional agencies weeks to produce and learn why starting with Lindy or n8n beats jumping straight to building custom SDR systems.

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www.yoodli.ai

Connect with Varun: https://www.linkedin.com/in/varun-puri001/

Why Communication Is THE New Competitive Advantage for GTM

Varun Puri, CEO of Yoodli, explains why AI role plays aren't just a feature—they're the future of how sales teams practice and win.

From his days running special projects at Google under Sergey Brin to building a platform used by Fortune 50 companies, Varun shares what most AI misses about communication, why information commoditization changes everything, and why the best sales coaches are partnering with (not competing against) AI.

If you're in GTM, enablement, or sales leadership, this is essential.

TIMESTAMPS:

00:00 — Intro

KEY QUOTES:

"Two out of three people struggle with communication confidence."

"You can use Excel, but there's a reason you use a CRM."

"When information becomes a commodity, the only thing that separates top performers is how they show up.

More on AI + GTM:

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www.evergrowth.io

https://www.linkedin.com/in/jbdaguene/

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www.chilipiper.com

Connect with Alina: https://www.linkedin.com/in/alinav/

In this conversation with Coach K, Alina—Co-CEO of Chili Piper—reveals the uncomfortable truth about AI that nobody's talking about: it won't replace your job, but it WILL force you to completely reinvent yourself.

She walks through her journey from communist Romania with a "CEO or bust" mentality, to a devastating realization that she couldn't save everyone, to now leading a company navigating the biggest technological shift of our lifetime. But here's the thing—she's not afraid anymore. And she explains exactly why you shouldn't be either.

WHAT YOU'LL LEARN:

How Alina went from paralyzed confusion about AI replacing her employees to genuinely excited about what's possible. She breaks down the one thing most companies get wrong when building AI infrastructure (hint: it's not about the tools—it's about alignment).

You'll hear the behind-the-scenes story of how Chili Piper unified their data across sales, marketing, and customer success into Snowflake, then used it to answer questions like "Why do buyers actually switch to us?" and "What messages actually move deals?" The answer? It took locking their team in a room and forcing executives to leave their egos at the door.

Then she shares the framework for automating soul-crushing tasks without destroying your team—and why the future of GTM is actually MORE human, not less.

THE MINDSET SHIFT:

The biggest insight isn't about technology. It's this: AI amplifies what makes YOU unique. It can't replace you. It can augment you. And everyone who's terrified right now is missing the most important opportunity of their career.

"We're all phoenixes in the ashes right now," Alina says. This is the conversation about what that actually means—and what you need to do about it.

PERFECT FOR: GTM leaders, founders, SDRs, marketers, anyone feeling overwhelmed by AI and wondering where to actually start.

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https://www.surepeople.com/

Russell-> https://www.linkedin.com/in/russell-mikowski-a349903/

GTM AI Podcast Episode: Russell Mikowski on AI-Powered Psychometrics and the Human Advantage

In this episode, Jonathan Kvarfordt interviews Russell Mikowski, CEO of SurePeople, about revolutionizing workplace psychometrics through AI integration. Russell shares his unconventional journey from DJ and poker player to CEO, and reveals why personality-driven collaboration becomes MORE critical as AI automates routine tasks. The conversation explores how organizations can optimize human interactions, the "desk drawer problem" with traditional assessments, and the future of AI agents that understand personality psychology.

Russell explains how traditional psychometric assessments fail to deliver ongoing value.

Key Quote: "The results of those assessments are often metaphorically stuffed into our desk drawers, sometimes literally in Manila folders and kind of die there. Right? So sure people is looking to completely disrupt the traditional psychometric world by democratizing access to psychometrics across organizations."

Discussion of SurePeople's approach to personality measurement and real-time application.

Key Quote: "Prism is the most accurate psychometric on the market today. So we're comfortable that our tool is the appropriate vehicle for powering interactions that matter in moments that matter on platforms that you already use."

Russell explains how personality insights drive tangible business outcomes.

Key Quote: "Should they be leading with the why? Because the group leans towards Big picture thinking... Or should they get straight to the details and the data? Because this group doesn't care at all about how your kids are, or even why the company has made this decision."

Key Quote: "Culture begets performance right. If people feel seen, heard, and understood, they're less likely to be flight risks, they're less likely to be quiet quitting, they're less likely to be negatively impacted by a slack message that they took the wrong way."

Exploring how personality data could enhance AI communications and reduce "robot speak."

Key Quote: "What if your personality, as determined by a psychometric, could be essentially fed into an agent to make the language that it uses sound more like you. And then there would be consistency, perhaps, between that initial automated outreach, and how you actually act when you get on a demo with someone."

Russell's core thesis on why human interactions become more valuable, not less, as AI advances.

Key Quote: "The expected output, and you know, in a related manner, the value of each human individual on teams is rising right?... So the optimization of the interaction, the communication, the collaboration between more valuable than ever human resources."

Key Quote: "As a big picture thinker... I'm bad with details. I'm horrible with lists... But where AI can stay on top of those for me make reminders and keep me informed... That's freeing up my time to think creatively about what the next great product might be."

Russell shares surprising findings about who adopts AI-powered personality tools.

Key Quote: "A pattern is starting to form that would show people who have more what we would call precise personality types. So those are like your architects, your scientists, your research... are more likely to use our tools more often."

Information on accessing the PRISM assessment and company contact details.

Key Quote: "Any company that wants to deploy the assessment between 50 and a thousand employees just simply schedule a demo via our site, and we'll give you the option to roll it out for free forever to all of your employees."