How to Do Better Email Marketing
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
Email marketing is alive and thriving, but the playbook needs an urgent rewrite. (02:30) In this Exit Five live session, head of marketing Jess Lytle hosts a roundtable with email experts to decode what's actually working in email, SMS, and in-app messaging right now. The conversation tackles how AI has changed the inbox landscape, making it harder than ever to stand out, while revealing strategies that cut through the noise. (05:58) The discussion covers practical tactics from human-centric sender strategies to behavioral triggers, personalization without being creepy, and measuring success when email plays an assist role rather than hero.
- Core theme: Moving from spray-and-pray email blasts to behavior-driven, human-centered messaging that earns attention and drives genuine engagement
Speakers
Jess Lytle
Head of Marketing at Exit Five, stepping in as host for this session. Previously served as Director of Demand Generation at a PLG vertical SaaS organization where she extensively used Customer.io for 30-day trial onboarding flows.
Gabby Kussner
Lifecycle marketing and growth marketing expert at Customer.io for six years, based in New York City. She covers user onboarding and activation series, specializing in behavior-driven messaging workflows.
Alyssa Armstrong
Runs an email marketing agency helping both D2C and B2B brands with email and SMS marketing strategies. Based outside Seattle, she's known for her human-centered approach to email copywriting.
Joe Cunningham
Email marketing consultant and copywriter based in North Philadelphia. He has edited hundreds of emails and newsletter ads for Stack Marketer digital marketing newsletter and works with SaaS and tech brands on event emails and cold outbound campaigns.
Key Takeaways
Treat Email Like Personal Space, Not a Billboard
The inbox is fundamentally a personal space that requires respect and intentionality. (12:03) As Alyssa emphasized, "The inbox is like a personal space. Anytime I'm writing an email, if someone invited you into their inbox, I'm gonna treat that with respect." This mindset shift from broadcasting to conversing changes everything about how you craft messages. Instead of treating emails like advertisements, approach them as if you're writing to a friend who invited you into their home. This means understanding your role in their inbox, creating narrative continuity between emails, and always asking for replies to foster genuine engagement rather than one-way communication.
Human Senders Beat Brand Senders Every Time
The email inbox is becoming more like a social feed where people instinctively look for names instead of company logos. (08:34) Joe noted seeing "more companies sending emails from team members" with personal signatures, and how he naturally gravitates toward emails from specific people like "Mark Huber's emails from User Evidence" rather than generic company sends. The strategy goes deeper than just changing the sender name – successful companies are routing replies back to actual team members and creating authentic personal connections. This human-centric approach builds trust and engagement because recipients feel they're communicating with a real person rather than a faceless corporation.
Relevance Trumps Volume in the AI Era
With AI flooding inboxes with generic content, the bar for earning attention has never been higher. (15:48) The key differentiator isn't sending more emails – it's sending the right emails to the right segments with stories that actually connect to their specific circumstances. As the panel emphasized, "relevance over volume is critical right now." This means understanding your ICP deeply enough to craft messaging that doesn't feel like AI-generated weasel words. Successful marketers are investing time in genuine research, creating detailed audience segments, and connecting product updates to real workflow improvements rather than blasting feature announcements to everyone.
AI Personalization Works Best for Cold Outreach, Not Nurture
The panel revealed a fascinating insight about AI personalization effectiveness across different campaign types. (15:25) Joe's client saw significant revenue impact using AI personalization tools like Singulate for cold sponsor outreach, personalizing email sections based on industry, growth stage, and relevant case studies. However, Gabby found that for existing trial users, AI personalization drove high engagement but less free-to-paid conversion. The lesson: AI personalization excels when you need to break through noise with cold contacts who have zero context, but for warm audiences, authentic human connection and behavioral triggers often outperform AI-generated customization.
Measure Email Success Based on Its Actual Job
Stop using vanity metrics as your north star – instead, define what each email is actually supposed to accomplish and measure accordingly. (38:01) As Joe explained, "what really is the outcome that we want from this email?" For event follow-up emails, success might be who's reading and replying, not just open rates. For nurture campaigns, it might be sustained engagement over time rather than immediate clicks. The panel emphasized looking at contact frequency before conversion, understanding the full customer journey, and recognizing that many valuable subscribers are "lurkers" who read consistently but don't click – yet still convert when ready. Email attribution is never perfect, but measuring the right outcomes for each campaign's purpose provides much clearer strategic direction.
Statistics & Facts
- Customer.io has been serving as a data-driven messaging platform for over six years, with Gabby noting their extensive experience in B2B SaaS lifecycle marketing. (06:02)
- Exit Five's community has grown to nearly 5,000 members, as mentioned in the outro, demonstrating significant growth in their B2B marketing community. (61:15)
- Customer.io recently surveyed 600 marketers to understand current lifecycle marketing trends and challenges, indicating the scale of research being conducted in the email marketing space. (62:46)
