10 AI mistakes wrecking your retention

<p>Download our 4-part briefsheet for better AI prompts &gt;&gt; www.ecomemailmarketer.com/ai-prompt-brief</p><p><br></p><p>AI won’t fix a weak retention program. It’ll just help you break it faster.</p><p><br></p><p>In this episode of the Send It Podcast, Jimmy Kim and Chase Dimond get into the real AI conversation email and SMS marketers should be having: where AI actually helps, where it quietly hurts, and why the tool itself isn’t the advantage anymore.</p><p><br></p><p>From generic subject lines and fake-looking imagery to black-box segmentation and overhyped ESP features, this episode breaks down how ecommerce brands can use AI without losing the trust, voice, and strategic judgment that make retention marketing work.</p><p><br></p><p>EP 89: 10 AI mistakes wrecking your retention</p><p><br></p><p>Here&#39;s what we&#39;re diving into:</p><p>- Why AI-generated subject lines are making every brand sound the same</p><p>- How fake-looking AI imagery can erode customer trust</p><p>- Why “AI-powered” ESP features still need to prove their lift</p><p>- How to build AI workflows with prompts, brand context, and QA checks</p><p>- Why the future belongs to strategic, AI-native retention marketers</p><p><br></p><p>Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!</p><p><br></p><p>Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/</p><p><br></p><p>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 &amp; SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/</p><p><br></p><p>______</p><p><br></p><p>00:00 Welcome to the show</p><p>03:35 Hot take 1: AI subject lines make every brand sound the same</p><p>06:38 Hot take 2: AI imagery is quietly costing you trust</p><p>12:20 Hot take 3: If you&#39;re not using AI, you&#39;ll fall behind</p><p>16:16 Hot take 4: AI segmentation is a dangerous black box</p><p>20:13 Hot take 5: AI copy needs way more editing than anyone admits</p><p>25:05 Hot take 6: Your AI workflow is the real moat</p><p>29:49 Hot take 7: ESPs are massively overselling their AI</p><p>34:48 Hot take 8: Human in the loop is worth more than you think</p><p>38:19 Hot take 9: AI is about to make everyone sound the same</p><p>43:27 Hot take 10: The retention marketer&#39;s job is changing fast</p><p>46:43 Final thoughts and what to comment below</p><p><br></p><p>______</p><p><br></p><p>Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, &amp; exclusive industry news! http://ecomemailmarketer.com/</p><p><br></p><p>______</p><p><br></p><p>Follow Jimmy &amp; Chase on social!</p><p><br></p><p>Follow Jimmy Kim at: </p><p>https://x.com/yojimmykim</p><p>https://www.linkedin.com/in/yojimmykim/</p><p>https://www.instagram.com/yojimmykim/</p><p>https://www.tiktok.com/@yojimmykim </p><p><br></p><p>Follow Chase Dimond at: </p><p>https://x.com/ecomchasedimond</p><p>https://www.linkedin.com/in/chasedimond/</p><p>https://www.instagram.com/chasehunterdimond/</p><p>https://www.tiktok.com/@chasehunterdimond</p><p><br></p><p>Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!</p>