How to Do Better Email Marketing — The Dave Gerhardt Show (from Exit Five)

#312 | Jess Lytle (Head of Marketing at Exit Five) hosts a roundtable with a group of email experts on what’s actually working in email, SMS, and in-app messaging right now. They dig into AI’s impact on the inbox, how to sound human when everyone’s using the same tools, and why relevance beats volume. The group also breaks down how to personalize without being creepy, what to do with “lurkers” who never click but still convert, and how to build messaging that survives the AI slop era. It’s a sharp look at how B2B marketers can cut through the noise, earn attention, and actually get people to respond.

Timestamps

(00:17) - — Jess welcomes everyone
(01:22) - — Why email and messaging aren’t dead… bad messaging is
(04:50) - — How AI changed the inbox and why standing out is harder than ever
(05:26) - — Why human senders beat brand senders in email
(08:55) - — Writing emails like you were invited into someone’s personal space
(11:10) - — Balancing stakeholder requests vs. what your audience actually wants
(14:20) - — Real talk on AI personalization, enrichment, and where it actually works
(20:25) - — Subject lines, preview text, and how people really decide what to open
(22:00) - — Email stories and empathy-driven content that outperform
(27:55) - — SMS, in-app, and email orchestration: what to use when
(34:00) - — Measuring impact when email is assist, not hero
(42:00) - — The future: AI-driven workflows, data challenges, and what’s coming
(50:40) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them

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Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.

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