Episode Details

#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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Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Join the next cohort of Opal U, a live 5-day course designed for senior marketing leaders who are ready to ship more with AI, at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

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.

Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

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Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

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