30:55The Retention Roadshow
The Retention Roadshow
Email and SMS Retention Strategy with Jimmy Kim
Jimmy Kim lays out a practical retention framework covering customer journeys, segmentation, email and SMS, AI, and a 90-day plan for a healthier program.
Watch it. Put it to work.
ABOUT THIS SESSION
Build relationships that repeat.
Jimmy Kim lays out a practical retention framework covering customer journeys, segmentation, email and SMS, AI, and a 90-day plan for a healthier program.
For founders, retention leaders, and operators rebuilding an email and SMS strategy.
A re-recorded presentation from the June 2026 Retention Roadshow. The original live recording was unavailable; this version was published in July 2026.
- Speaker
- Jimmy Kim
Founder & CEO, eCom Email Marketer - Event edition
- The Retention Roadshow ↗
June 2026
Speaker roles and platform examples reflect the session’s original context. This is an archived conversation.
TAKE IT BACK TO YOUR DESK
Ideas to put to work.
- 01
Choose the outcomes first
Map each major message to a customer outcome rather than a slot on the calendar.
Read this part · 02:55 ↓ - 02
Move beyond engaged versus unengaged
Give prospects, one-time buyers, repeat customers, and subscribers different messages.
Read this part · 10:32 ↓ - 03
Give email and SMS different roles
Audit email and text together so the second touch adds something useful.
Read this part · 15:04 ↓ - 04
Use AI without losing the human layer
Use AI to analyze and vary your work while people own the original idea and customer relationship.
Read this part · 18:40 ↓ - 05
Measure the customer base you can reach
Track active subscribers and time to second purchase, then use the findings to prioritize the next 90 days.
Read this part · 28:23 ↓
READ THE SESSION
The edited transcript.
A condensed, edited reading version based on the YouTube captions and session chapters. Repetition and unclear audience audio have been removed; the discussion is paraphrased for clarity, rather than presented as a verbatim transcript. Timestamps refer to the original video.
Original recording on YouTube ↗Choose the outcomes first
Jimmy organizes retention around four outcomes: shorten the path to a first purchase, improve repeat purchasing, increase order value, and grow lifetime value. Those goals give campaigns and automations a purpose beyond keeping the sending calendar full.
The customer journey continues after checkout. Onboarding, first use, a second purchase, emotional connection, and advocacy each require a different conversation. Mapping those moments exposes gaps that a campaign revenue report alone may not show.
Move beyond engaged versus unengaged
Engagement and behavioral triggers are the first layers of segmentation. Jimmy then distinguishes prospects, one-time buyers, repeat buyers, and subscribers. A customer’s relationship with the brand changes what they need to hear, even when the product being promoted is the same.
Predictive signals and information customers provide can add more context, but they work better on top of a clear lifecycle structure. Segmentation should change timing, tone, or message. Creating another list without changing the experience is not the objective.
Give email and SMS different roles
SMS should not read like a shortened duplicate of the email. Jimmy describes email as a place to explain, tell stories, and build context, while a text can deliver a timely, concise reason to act. The two channels should work together across the journey.
Look at the total experience a customer receives. A campaign, triggered email, and text can all arrive close together. Coordinating those touches helps make the program feel like a conversation instead of several disconnected teams competing for attention.
Use AI without losing the human layer
The talk recommends AI for performance analysis, test variations, and tasks that consume time without requiring a new brand idea. Connecting an assistant to an email platform can make it easier to spot a trend and investigate what changed.
Jimmy still places the brand’s memory, voice, and relationship with the customer in human hands. He favors generating variations from a strong starting idea rather than treating the first AI draft as the creative strategy. Review the outputs for relevance before putting them into the program.
Measure the customer base you can reach
A large historical list can disguise a much smaller active audience. Jimmy suggests watching the number of reachable, engaged subscribers and the time between first and second purchase, alongside cohort value. The useful trend is whether those customers are becoming more valuable and responsive.
The closing 90-day plan turns the framework into staged work: establish the basics, improve the journey, and then optimize. Start with missing core flows and obvious experience problems before investing in increasingly elaborate personalization.
KEEP THE IDEAS COMING
Stay in the conversation.
3 SESSIONSPLAY IT BACK. PUT IT TO WORK.
30:55
1:13:26The Retention Roadshow
The 2026 Email Flow Playbook
46:21The Retention Roadshow
The Anatomy of The Golden Goose
YOUR NEXT STEP: IN THE ROOM
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