Podcast Summary: "How to Do Better Email Marketing"

The Dave Gerhardt Show | Exit Five
Episode Date: December 15, 2025

Overview

This episode, guest-hosted by Jess Lytle due to Dave Gerhardt recovering from surgery, is a deep dive into practical, up-to-date email marketing strategies. The panel features Jess (Head of Marketing, Exit Five), Gabby Kustner (Lifecycle Marketing, Customer IO), Alyssa Armstrong (Email/SMS Agency Owner), and Joe Cunningham (Email Marketing Consultant). Together, they address what's really working in email, SMS, and in-app messaging for 2025-2026, how AI is impacting the field, and actionable tactics for B2B and D2C brands.

Key Discussion Points & Insights

1. Email’s Enduring Value & Humanization of Messaging

• "Everybody, these days, every week, I feel like someone's popping up and declaring like, email is dead. It's not working...Meanwhile, I know for a fact marketers are still out there driving millions in revenue from email." – Dave Gerhardt [02:00]
• The panel unanimously rejects the "email is dead" narrative. Instead, they emphasize that strategy and execution—not the channel—determine results.
• Email remains the only channel where marketers truly own their audience and relationships.

Emergence of ‘Personal’ Sender Identities

• More companies are sending emails "from" individuals (team members) rather than the brand to humanize communications.
  • "I almost instinctively look for names in my inbox and not so much company names." – Joe Cunningham [08:22]
  • Adding a signature or photo increases open rates and builds connection.

Real Human Tone Cuts Through the Noise

• Stand out by making emails sound like genuine, individual communication—not robotic, templated marketing.
• "Filtering your emails through that [‘they invited you into their inbox’] perspective… treat them like an actual person." – Alyssa [11:54]
• Narrative, distinct voice, and occasional vulnerability (e.g., using an intern as a consistent 'sender') foster engagement.
• AI-generated content risks uniformity; personal touch is essential.
• "Pretend you're writing to your best friend." – Gabby [13:06]

2. Balancing Stakeholder Demands vs. Audience Value

• Challenge: Stakeholders often want to cram product updates and company news into every message.
  • "If we include the nine new product releases this month, literally no one will have read about any of them." – Gabby [14:24]
• Marketers must act as advocates for the reader: curate, segment, and provide only relevant, valuable information.
• Relevance over volume: It's better to send targeted, valuable info than mass "blasts." [16:19]

3. How AI is Changing Email Marketing

• AI is widely adopted for copywriting, personalization, and workflow automation, but has to be handled thoughtfully to avoid generic, forgettable copy.

• Personalization at Scale:

  • Example: Joe used Singulate AI to customize case studies and references for cold outreach, resulting in more revenue.
  • Gabby notes it's more effective for new/outbound prospects than for current users.
  • "Each email that every contact got was slightly different." – Joe [19:01]

• LLM (Large Language Model) Limitations:

  • AI-generated copy often defaults to generic tone and structure.
  • Human input is needed for high-quality, authentic final outputs.

• Tips for AI Workflow:

  • Treat your content as "data"—train AI on your best human-written content and use human editors for finishing.
  • Build modular workflows: create and review email/newsletter sections separately for better quality.
  • Add spontaneous, human touches (jokes, GIFs, anecdotes) for authenticity.

4. Cracking Subject Lines and Open Rates

• The three main factors influencing opens:
  1. Subject line quality
  2. Sender recognition
  3. Timing
• Alyssa recommends self-reflection: "What made me open this email?" [23:26]
• Consistency in sender identity and tone builds trust; don’t rely on gimmicky subject lines unless it matches your brand persona.

5. Tactical Successes: What Really Resonates

• Non-marketing content that taps into broader human themes (e.g., burnout, routines) can outperform traditional value props.
  • Jess: "It had nothing to do with marketing also, which is interesting. This is a marketing newsletter… but it was about, how are you managing your mornings?" [24:39]
• Diversifying content to address the whole person (not just their business needs) fosters connection and replies.

6. Deliverability, Cold Domains, and Channel Orchestration

• Deliverability: Always warm up new domains and avoid mass cold outreach without consent—otherwise, risk deliverability issues.
• Use email in conjunction with LinkedIn and other channels—don’t silo your efforts.
• Example: Email can be a "closing" or "assist" channel (reinforcing contacts made elsewhere).

7. Channel Mix: Email, SMS, and In-App Messaging

• B2B SaaS: Email and in-app are primary; SMS is rarely appropriate unless for urgent, transactional, opted-in communications (e.g., event reminders).
• D2C: SMS effective for urgent, promotional, or highly relevant touches—use sparingly and always add value (like event reminders with Google Maps links).
  • "If there's a time where they're specifically going to be on their phone, we might lean more towards SMS or in-app…" – Alyssa [34:28]
• In-app messaging should be driven by behavioral triggers and used thoughtfully to avoid notification fatigue.

8. Measuring Success & Attribution

• Opens and clicks matter, but ultimate success varies by email purpose.

  • Nurture/educational = engagement over time
  • Closing = conversions (demos, signups)
  • Event follow-up = replies and continued conversation

• "Measure it fairly based on the job you had it do." – Jess [39:34]

• Analyze contact frequency before conversion, watch for "lurkers" who don't click but read, and track unsubscribe narratives.

• Unsubscribers can signal over-messaging or irrelevant content.

9. Advanced Tactics, AI Applications, & The Future

• AI’s role is expanding into:
  • Lead magnet creation
  • Customer support for lead capture (e.g., via chat tools like ManyChat)
  • Testing messaging on mock personas (using LLMs like Claude, ChatGPT, NotebookLM)
• LLM models can be used to analyze ICPs and suggest campaign optimizations, but still need human oversight.
• Best-in-class example: NotebookLM—AI drawing only from your uploaded company documents (removes hallucination, integrates with Google Drive).

Forward-looking: Adaptive Messaging via LLMs

• Gabby wonders about the future: AI models that "just spit out in a timely manner the action they need… if they've done 1, 7, and 9, what the next best thing is." [45:54]
• The panel agrees this is coming soon (especially for D2C); B2B is catching up as data integration matures.

10. Best Practices for In-App Messaging & User Journeys

• Avoid overloading users with in-app prompts; coordinate across teams to not overwhelm new users.
• Behavioral triggers and segmented user journeys work best.
• Use "micro wins" (Zapier example) to guide users step-by-step toward activation and deeper usage.

11. Reputation & List Hygiene

• Actively segment by engagement—monitor, attempt to re-engage, and sunset unengaged contacts to protect sender reputation and deliverability.
  • "Have that policy in place... It doesn't make sense to keep emailing people who are not engaging." – Joe [59:48]
• Use phased re-engagement nudges, then prune aggressively if no response.

Notable Quotes & Memorable Moments

• "Messaging isn't dead, bad messaging is." – Jess [03:13]
• "At some point all the LLMs will sound the same… what each individual person can contribute is their tone of voice." – Gabby [13:06]
• "Death to blasting, as they say in the chats. That is the thing that does need to be dead." – Jess [16:19]
• "Sometimes, just reminding people to do things is good marketing if it's really helpful and useful." – Jess [41:34]
• "Treat your content as data. Train your LLMs on your best human content, and always have a human editor in the loop." – Joe [19:01–23:00]
• "People are opening all these emails but they're not taking the action I want them to take. So why is that?" – Gabby [33:04]

Important Timestamps

• [08:22] Humanizing sender identity in emails
• [11:54] Treating the inbox as a personal, invited space
• [16:19] Focusing on relevance, not volume—the end of blasting
• [19:01–23:00] Deep dive on AI personalization & workflow tips
• [23:26] Factors influencing email opens: subject, sender, timing
• [24:39] Example: Story-driven, non-marketing content driving engagement
• [29:17] Email as a closing or assist channel, multi-channel strategy
• [34:28] When to use SMS vs. email or in-app messaging
• [39:34] Measuring email by its assigned "job," not vanity metrics
• [45:54] The role of AI/LLMs in future customer journey orchestration
• [53:02] In-app journeys and use case storytelling for user onboarding

Resource Recommendations

• AI Tools: Singulate AI, Claude, ChatGPT, NotebookLM
• Lead Capture Automation: ManyChat
• Customer Data-Driven Messaging Platforms: Customer IO
• Newsletter Promotion: Use multiple channels, avoid intrusive pop-ups (slide-outs, footers, resource links)

Final Takeaways

• Email remains unrivaled for direct, owned communication—if used with respect for the audience and sharp segmentation.
• Personal tone, narrative, and sender authenticity beat AI-generated generic messaging every time.
• AI should supercharge, not replace, human creativity—use it for personalization, workflow, and segmentation, but always keep a “human in the loop”.
• Tactical orchestration of email, SMS, and in-app messaging depends on audience, context, and behavioral triggers.
• Your measurement of success must align with the specific job of each message, not just default to open rates or clicks.

Panelists

• Jess Lytle (Host): Head of Marketing, Exit Five
• Gabby Kustner: Lifecycle/Growth Marketing, Customer IO
• Alyssa Armstrong: Owner, Email/SMS Agency (B2B + D2C)
• Joe Cunningham: Consultant & Copywriter for B2B/SaaS/newsletters

Sponsors: Customer IO

For more actionable discussions and resources, check out exitfive.com and the Exit Five community.