How to Do Better Email Marketing

#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 Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more