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:Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.***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