Empathy-Driven Stories Win

#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
• (02:30) - — Why email and messaging aren’t dead… bad messaging is
• (05:58) - — How AI changed the inbox and why standing out is harder than ever
• (06:34) - — Why human senders beat brand senders in email
• (10:03) - — Writing emails like you were invited into someone’s personal space
• (12:18) - — Balancing stakeholder requests vs. what your audience actually wants
• (15:28) - — Real talk on AI personalization, enrichment, and where it actually works
• (21:33) - — Subject lines, preview text, and how people really decide what to open
• (23:08) - — Email stories and empathy-driven content that outperform
• (29:03) - — SMS, in-app, and email orchestration: what to use when
• (36:20) - — Measuring impact when email is assist, not hero
• (44:20) - — The future: AI-driven workflows, data challenges, and what’s coming
• (53:00) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. 

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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