AI just predicted the future of retention marketing… but is it accurate?
In this episode, Jimmy Kim and Chase Dimond ask ChatGPT to generate bold 2026 predictions for ecommerce email and SMS marketers and then break down what they agree with, what’s BS, and what might already be happening.
From segmentation going predictive to retention teams owning margin and profit, this episode is packed with strategic insights and real-world examples from brands, agencies, and operators doing the work.
EP 61: Here's what AI says about retention marketing in 2026
Here's what we're diving into:
- Why your flows might be worth more than your campaigns
- What retention marketers will actually be judged on in 2026
- Predictive segmentation, emotional copywriting, and deliverability as a job requirement
- How SMS will get leaner and more profit-focused
- The rise of behavioral targeting over traditional KPIs
Thank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!
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eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://eemtrk.com/eec-sendit
Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox
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00:00 Welcome to the Show
04:26 Cohort Yield vs. Campaign Revenue
06:44 Flow Weight vs. Campaigns
10:32 Strategic Use of SMS
13:13 Importance of Deliverability
15:32 Predictive Segmentation
17:55 Creative Testing: Emotion vs. Design
18:13 Behavioral Copy Strategies for Marketers
20:40 The Future of Preference Centers
23:37 Profit Accountability for Marketers
25:27 Retention Marketers and Replenishment Control
29:13 Job Security Tied to Returning Customers
31:15 The Role of AI in Marketing
34:59 Conclusion and Final Thoughts
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Follow Chase Dimond at:
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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!