About this episode (#406):

In this episode, Jack and Jeremy revisit the question: should AI be trusted to write and send first-line personalization in cold outreach? It’s late Q2 2025, and AI tools are smarter than ever. But are they smart enough to handle something as nuanced (and reputation-sensitive) as email intros without human review? The guys go deep on how far the tech has come, what’s still risky, and where it might actually make sense in your workflow.

Key topics discussed in this episode:

Why letting AI send unchecked intro lines is still a risky move
How the quality of personalization has improved and where it still breaks
Why buyer awareness of AI is making personalization harder, not easier
The evolving role of the first line (and why the PS line might be safer)
What makes a smart AI prompt and how to reduce hallucination risk
Testing AI-generated personalization vs. handcrafted lines
When AI might make sense for high-volume outbound vs. niche campaigns

This episode is a no-fluff look at what AI can and can’t do for outbound personalization in 2025. Jack and Jeremy break down the tradeoffs, the risks, and where smart filters and prompts can actually help without wrecking your reply rates.

About the hosts:

Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/

Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

#406 - Don’t Let AI Cripple Your Reply R...