December 15, 2025

How to Do Better Email Marketing

1 hour 3 minutes

#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

(03:06) - — Why email and messaging aren’t dead… bad messaging is

(06:34) - — How AI changed the inbox and why standing out is harder than ever

(07:10) - — Why human senders beat brand senders in email

(10:39) - — Writing emails like you were invited into someone’s personal space

(12:54) - — Balancing stakeholder requests vs. what your audience actually wants

(16:04) - — Real talk on AI personalization, enrichment, and where it actually works

(22:09) - — Subject lines, preview text, and how people really decide what to open

(23:44) - — Email stories and empathy-driven content that outperform

(29:39) - — SMS, in-app, and email orchestration: what to use when

(37:08) - — Measuring impact when email is assist, not hero

(45:08) - — The future: AI-driven workflows, data challenges, and what’s coming

(53:48) - — 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. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing.

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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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By Exit Five

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