Send It!

The Legal Loophole Behind Non-Opt-In Email MarketingIs it actually legal to email people who never opted in? This week, Jimmy Kim sits down with Adam Robinson, founder of Retention.com and RB2B, to break down how identity resolution and non-opt-in email marketing actually work, and why it’s compliant under U.S. law even though most people assume it isn’t.Adam built Retention.com (formerly GetEmails) into the market leader in this space, and in this episode he explains exactly how the legality works, how deliverability actually gets protected, and what separates a smart list growth strategy from one that gets a brand blacklisted.What we cover:→ Why non-opt-in email marketing is legal under CAN-SPAM, and why so many people think it isn’t→ The 1-2% rule that keeps deliverability safe when adding non-opt-in contacts→ Who this strategy actually works for (hint: it’s not a brand new store)→ The difference between Retention.com’s two products: aggressive list growth vs. conservative cart recovery→ Why the biggest Shopify brands use multiple identity vendors at once, not just one→ How Adam priced RB2B at $79/month instead of a $12,000 sales-led deal, and why→ Why events and in-person relationships still drive most vendor decisions in ecommerceIf you’ve been skeptical about identity resolution tools or unsure whether they’re worth the risk, this episode answers the questions most people are too embarrassed to ask.Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom 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://www.ecomemailcertified.com/______00:00 Intro00:47 Welcoming our guest01:43 Is this legal? Breaking down CAN-SPAM02:48 Compliance Explained05:22 Deliverability Strategy: The 1-2% deliverability rule07:43 Who Should Use It10:40 Optimization Not Magic12:05 Real World Use Case14:00 Grow vs Reclaim15:46 Competitors Copycats17:50 Data Sources Providers21:28 Events, community, and how this market actually buys23:01 Pricing Shakeup: You lowered the price?26:21 Final questions and outro______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Everyone's copywriting "rules" are recycled from 1960s direct mail and copywriting Twitter . In this episode, Jimmy Kim and Chase Dimond go through 10 sacre copywriting rules and explain why most of them no longer hold up in 2026 inboxes and beyond.From why long-form email is quietly outperforming short copy, to why the "one CTA per email" rule is only half right, to why first name personalization barely moves the needle anymore, this episode breaks down what actually converts vs. what copywriters keep repeating because everyone else does.What they cover:- Why long-form email copy is winning (and how AI changed the math)- The real rule behind CTAs: one goal, not one button- Why personalization tokens are overrated and segment-level relevance wins- Statement hooks vs. question hooks- Why most brand storytelling in email is wasted space- The most under-optimized line in your email (hint: it's not the subject line)- Why the PS line still converts and nobody uses it- Why trying to be funny in email usually backfires- Why fake urgency has trained your customers to ignore you- Writing email copy like you're texting a friend, not presenting to a boardThank you our friends at Omnisend and Retention.com for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastLet's hang out IRL! Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom 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://www.ecomemailcertified.com/______02:59 Hot Take 1: Long Copy06:46 Hot Take 2: Goal12:09 Hot Take 3: Personalization15:24 Hot Take 4: Question Hooks18:15 Hot Take 5: Storytelling21:20 Hot Take 6:The first line matters more than your headline25:02 Hot Take 7: PS Line Comeback28:21 Hot Take 8: Stop Trying Humor31:38 Hot Take 9: Urgency Overuse Trap36:29 Hot Take 10: Write Like You Text38:21 AI Makes It Corporate39:57 TLDR Wrap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/#emailmarketing #copywriting #ecommerce #retentionmarketing #klaviyoSend It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing: email, SMS, and ecommerce growth.Subscribe for new episodes every week.______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

No matter how good your abandoned cart emails are, most of that lost revenue never comes back. What if an AI could just call and ask why?In this episode of Send It, Jimmy and Chase talk with Will Nauseda, founder of Outcraft about the retention channel almost no one is using: voice. Outcraft built an AI that calls abandoned-checkout shoppers and has real conversations, answering the questions email and SMS can't. They get into why AI voice finally sounds human, why a call often recovers the sale without a discount, where it fits in your flow, what it actually costs, and why the early-mover advantage looks a lot like SMS three years ago.Find Will and Outcraft:Outcraft: https://www.outcraft.ai/?utm_source=Podcast&utm_medium=SendItWill Nauseda: https://www.linkedin.com/in/will-vilius-nauseda-a10278b1/Here's what they get into:- Why voice is the overlooked fifth retention channel- How AI voice got good enough to feel human, while staying disclosed- Why a call often recovers the sale without a discount- Where voice fits in your abandoned-checkout flow, and the quiet-hours rules- What it actually costs, priced per profile instead of per callThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comUpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616 ______00:00 Welcome to the show02:14 Meet Will Nauseda and the Outcraft story07:17 The abandoned cart intent email misses12:23 Breaking down a real AI voice call18:33 Where voice fits in your flow24:45 Why aggressive cart recovery wins26:31 The risks and guardrails of voice32:24 The low-risk way to test it35:10 The omni-channel, conversation-first philosophy38:33 Wrapping up and the future of voice40:16 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Ready Made Demand: The Retention Marketer's Guide to Cashing in on The Calendar - https://ecomemailmarketer.com/ready-made-demandRight now your customers are rebuilding their whole routine, and almost no brand is marketing to it.In this episode of Send It, Jimmy and Chase break down how to own a seasonal moment even if you've never sold a school supply in your life. Using back to school as the case study, a $147 billion season and the second biggest of the year, they lay out what actually makes a "moment," the framework for attaching your brand to one without it feeling forced, and the five plays that turn it into revenue. EP 94: The $147B season you're ignoringHere's what they get into:- Why back to school is a mindset, not a date, and the second New Year for your list- The three things that make a moment worth stealing- The stretch test for attaching your brand without it feeling forced- The five plays: bundles, routine stories, segmentation, urgency, and offers- The timing calendar, and why the moment already started back in JulyThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comUpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616______00:00 Welcome to the show03:14 Why this $147B moment matters right now04:22 What actually makes something a moment06:40 How any brand plays the routine reset11:27 The three-question framework for any moment12:58 The five plays that turn a moment into revenue18:31 Why the moment beats a discount19:32 The timing calendar, and why July already started it23:58 The metrics that tell you it actually worked24:47 Key takeaways and your low-risk first move26:13 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Patrick's team is just 12 people, but it outputs like a team of 100. That gap is the whole story of where marketing is going.In this episode of Send It, Jimmy talks with Patrick Haede, co-founder and CEO of Superscale AI, about how AI is changing what a marketer actually does. Having studied thousands of ad creatives, his case is simple: once building a product gets this easy, distribution becomes the moat and creative is the lever inside it.They get into why only about 5% of ads ever win, why the human moves up the stack to brand, judgment, and taste, and the meme with no logo that became a brand's best ad, plus why Patrick runs a 12-person company with the output of 100 agents.Here's what they get into:- The creative machine that beats guessing which ad will win- Why only about 5% of ads are ever real winners- How the marketer's job shifts from doing the work to orchestrating AI agents- The meme with no logo that became a brand's best-performing ad- What separates a 10x marketer from everyone else nowThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show01:59 Meet Patrick Haede and his founder journey04:48 The ecommerce family business behind the lens06:09 Why distribution is the new moat12:06 What actually makes an ad win16:49 The AI creative arms race is here21:30 How marketers become orchestrators of AI agents28:37 Inside Superscale AI34:00 Why verticalized AI tools are winning37:19 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Access our Black Friday & Cyber Monday cheat sheet: https://ecomemailmarketer.com/send-it/bfcm-2026The real question isn't what Black Friday makes you. It's what it costs you afterward.In this episode of Send It, Jimmy and Chase run 10 hot takes on Black Friday and Cyber Monday, and why most of the advice retention marketers have followed for five years is now outdated or actively working against them. They get into how extended sale windows killed urgency, how the send-more playbook torches your deliverability into January, and what to actually do differently before the season hits.EP 92: We're calling Black Friday 2026 right nowHere's what they get into:- Tighter sale windows, Thanksgiving sends, and the Cyber Monday profit brands overlook- Offer creativity that beats racing everyone to the deepest discount- Sending fewer, smarter emails and texts so BFCM doesn't torch your deliverability- The worst-LTV customers BFCM brings in, and running it as a retention play instead- Beating the self-inflicted post-BFCM slump and spreading revenue across the whole yearThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show02:59 Hot Take #1: Why Starting BFCM Earlier Is Hurting Sales05:59 Hot Take #2: Bigger Discounts Don't Win Anymore09:02 Hot Take #3: More Emails = More Damage During BFCM13:46 Hot Take #4: BFCM Customers Are Your Lowest-LTV Cohort16:49 Hot Take #5: Why Cyber Monday Can Be More Profitable Than Black Friday19:30 Hot Take #6: Why You Should Be Sending on Thanksgiving23:15 Hot Take #7: Your Q1 Slump Starts During BFCM25:59 Hot Take #8: Most Brands Are Destroying Their SMS List28:24 Hot Take #9: Stop Discounting Your VIP Customers32:34 Hot Take #10: BFCM Shouldn't Make or Break Your Business35:37 Key Takeaways & Wrap Up______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Unlock true 1:1 personalization: https://ecomemailmarketer.com/send-it/personalization-ladderPersonalization has been email's holy grail for a decade, yet we're still sending everyone the same email.In this episode of Send It, Jimmy Kim sits down with Liam Veregin and Jacob Paduch, co-founders of the agency Aplo and the AI personalization tool Allan, to get into what email personalization actually means in 2026. They break down why it's stayed a buzzword for a decade, why the wave of AI email builders solves a labor problem instead of the real one, and how borrowing Meta's creative-serving model changes what a retention program can do.Real personalization was never a first name in the subject line, it's the content, the offer, and the timing actually changing for each person.Check out allan:Website: https://getallan.comX: https://x.com/getallanaiLinkedIn: https://www.linkedin.com/company/getallan/EP 91: Unlock true 1:1 email personalization Here's what they get into:- How Meta serves creative, and why email never worked that way- Sending a genuinely unique email to every subscriber on your list- Why one-to-one content lifts revenue per recipient- Bolting personalization onto your ESP with no migration or IP warming- Where personalization goes next: on-site, CRO, and data enrichmentThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/______00:00 Welcome to the show02:28 Meet Liam and Jacob from Allan08:48 Why most personalization still falls flat18:04 Can small lists personalize? The labor problem23:24 Bringing paid ads logic to email26:10 The testing leverage you can't do by hand29:06 Covering more of your list without more work34:35 Where allan goes next, beyond email38:04 The Amazon-style experience DTC is chasing41:47 Final thoughts and where to try allan______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Access Jonathan’s FREE eCommerce Quiz Audit Button: https://optimizeyourquiz.com/research/best-and-worstEvery question your quiz asks costs the buyer something. And the best ones make it worth paying.In this episode of Send It, Jimmy Kim and Chase Dimond sit down with Jonathan Drake, who audited and ranked more than 3,000 ecommerce quizzes across 27 benchmark points to find out what separates the best quiz funnels from the worst.They dig into why the first question matters so much, how brands lose shoppers at the email and SMS capture step, when 6-9 questions can actually work, and why quizzes should feel more like guided product discovery than a default template built to collect zero-party data.Jonathan also shares what he learned from ranking the top and bottom ecommerce quizzes, including how visitor experience, business leverage, readability, product discovery, and lead capture all play into whether a quiz helps shoppers buy or just creates more data your team never uses.Follow Jonathan on social: https://x.com/JonathanDrakehttps://www.linkedin.com/in/jonathanrdrake/Here's what we're diving into:- The survey vs quiz difference most brands get wrong- Where quizzes lose people, and how to earn the email- Why more questions can actually mean a better customer- Using a quiz as a product discovery and selling tool- Where AI and the "conversation" model fit inThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastWant to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show02:25 Meet Jonathan Drake: 18 years in email and data marketing07:46 Why he audited 3,000 ecommerce quizzes12:18 The survey vs quiz difference most brands miss18:46 A tour of the quiz scoring dashboard20:54 The push and pull between business and customer23:25 How long a quiz should actually be26:02 Breaking down a great candle quiz live31:41 AI, conversations, and the Jack principles36:26 The worst quizzes and the zero-party data trap37:52 Quizzes vs pop-ups, and which protects your margin43:04 Final thoughts and conclusion______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Download our 4-part briefsheet for better AI prompts >> www.ecomemailmarketer.com/ai-prompt-briefAI won’t fix a weak retention program. It’ll just help you break it faster.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.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.EP 89: 10 AI mistakes wrecking your retentionHere's what we're diving into:- Why AI-generated subject lines are making every brand sound the same- How fake-looking AI imagery can erode customer trust- Why “AI-powered” ESP features still need to prove their lift- How to build AI workflows with prompts, brand context, and QA checks- Why the future belongs to strategic, AI-native retention marketersThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/______00:00 Welcome to the show03:35 Hot take 1: AI subject lines make every brand sound the same06:38 Hot take 2: AI imagery is quietly costing you trust12:20 Hot take 3: If you're not using AI, you'll fall behind16:16 Hot take 4: AI segmentation is a dangerous black box20:13 Hot take 5: AI copy needs way more editing than anyone admits25:05 Hot take 6: Your AI workflow is the real moat29:49 Hot take 7: ESPs are massively overselling their AI34:48 Hot take 8: Human in the loop is worth more than you think38:19 Hot take 9: AI is about to make everyone sound the same43:27 Hot take 10: The retention marketer's job is changing fast46:43 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Steal our notes from the Retention Roadshow: https://ecomemailmarketer.com/notes-from-retention-roadshowWe just spent a week on the road talking retention marketing with ecommerce teams across New York, Miami, Los Angeles, and Austin.And one thing became pretty clear: the conversations happening online don't always match what's actually happening inside ecommerce teams.In this episode of Send It, Jimmy and Chase recap the Commerce Roundtable Retention Roadshow, sharing the biggest takeaways from four cities, seven days, and hundreds of conversations with retention marketers and ecommerce operators. They dig into where teams really stand with AI, the strategies that kept coming up in every room, and the tactical ideas worth bringing back to your own program.If you want to keep a pulse on where retention marketing is actually headed, this episode is the place to start.Here's what we're diving into:- The real state of AI and MCP adoption across four cities- Why 85% of first purchases happen on day zero, and the double send for it- The 80/20 flow rule that's quietly wasting your time- Using an MCP to crack open the deliverability black box- Where to watch every full talk and grab the decks for freeWant to get in on the action? Replay all the Roadshow sessions here: The 2026 Email Flow Playbook: https://www.youtube.com/watch?v=7I4BDLim4t8Retention Marketing Playbook: https://www.youtube.com/watch?v=tMbTAGO-IJcEmail Marketing Myths Busted: https://www.youtube.com/watch?v=0z6jtSpwiyYConnected AI for Email & Retention Marketing: https://www.youtube.com/watch?v=AoPbAJllCrMThank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show06:11 How many marketers are actually using AI, city by city10:22 MCPs and connected AI, and why nobody knows them yet12:29 Max's welcome flow and pop-up playbook14:20 Philippe on early BFCM prep and the 80/20 rule16:12 Rytis on real MCP use cases, including deliverability19:05 The language and data that moves revenue21:30 Anwar on the metrics that forecast brand health22:46 Melanie's golden goose framework25:19 Coach Danny on building projections with AI26:34 Chris Lang on storytelling to grow a list31:12 Final thoughts and where to watch every talk______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Is your dashboard lying to you? Download our free vanity metrics cheat sheet: https://ecomemailmarketer.com/sendit-vanitymetricsThe metrics every retention team reports up to the CFO might be quietly making the company worse.Jimmy and Chase break down 10 hot takes on retention KPIs, why most of them are broken, and what to track instead. From inflated opens and bot-driven clicks to fake attribution, vanity list sizes, and the metrics leadership doesn't even know to ask for, this one's worth forwarding to your team and your founder. If you're making budget decisions, performance reviews, or strategy calls on numbers built before iOS privacy and bot click farms, you're probably operating on data that's lying to you.EP 87: We pulled the data on every retention metric brands track, here are the 10 broken onesHere's what they get into:- The bot click problem nobody is correcting for- How ESP attribution overcredits email and SMS- Why revenue per recipient hides what actually drove the win- Why industry benchmarks are mostly useless- The LTV math almost every brand is doing wrong- The metrics that predict program health (and nobody tracks)Thank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show01:25 Why your retention metrics are quietly lying to you03:22 Hot take 1: Open rates are fundamentally broken06:30 Hot take 2: Click rates are inflated by bots too10:28 Hot take 3: ESP attribution is mostly a fantasy14:23 Hot take 4: Revenue per recipient hides more than it reveals17:35 Hot take 5: List size is a vanity metric20:46 Hot take 6: AOV is the wrong way to measure most campaigns24:17 Hot take 7: Industry benchmarks are mostly garbage27:46 Hot take 8: Your LTV math is wrong32:09 Hot take 9: Unsubscribe rate isn't measuring what you think34:48 Hot take 10: The metrics leadership doesn't know to ask for38:27 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

After years of auditing retention programs, we're still seeing the same SMS mistakes.In this episode of Send It, Jimmy Kim and Chase Dimond share 10 SMS hot takes based on years of working with ecommerce brands and auditing retention programs. From discount-driven opt-ins and over-sending to MMS strategy, segmentation, compliance, and deliverability, they break down what's actually working in SMS right now; and what brands should stop doing immediately.EP 86: After auditing hundreds of brands, here are the 10 SMS mistakes we keep seeingHere's what we're diving into:- Why discount-driven SMS opt-ins often create low-quality subscribers- When MMS is worth the extra cost (and why most brands underuse it)- How often brands should actually be sending SMS campaigns- Why SMS segmentation should look different from email segmentation- The biggest compliance and deliverability risks brands overlookThank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditeCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show03:07 Quick compliance disclaimer before we get into it03:35 Hot take 1: Stop requiring a discount to get an SMS opt-in07:04 Hot take 2: MMS beats SMS for revenue almost every time09:44 Hot take 3: You should send way less SMS than you think12:28 Hot take 4: Two-way SMS is overrated for most brands16:34 Hot take 5: Transactional SMS is the most underrated surface in ecom19:12 Hot take 6: SMS segmentation shouldn't look like email segmentation22:21 Hot take 7: Keywords are wildly underused on SMS26:18 Hot take 8: Most SMS compliance is theater29:58 Hot take 9: Don't launch SMS until email is dialed in33:49 Hot take 10: Stop using SMS for things email does better36:08 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The email "best practices" everyone repeats are quietly costing your brand real money.In this episode, Jimmy Kim and Chase Dimond break down 10 hot takes on retention marketing that go against almost everything you've been told. From welcome series aggression to subject line strategy to why unsubscribes can actually be a good sign, they back every take with data and real-world experience across hundreds of brands.EP 85: We read every email marketing best practice and ranked the 10 worst onesHere's what they cover:- Aggressive welcome series make more money and clean your list at the same time- Subject lines and unsubscribes are tracked completely wrong by most marketers- Over-segmenting, over-testing, and over-designing are quietly hurting performance- Sending more often almost always beats sending less, when done with segmentation- Black Friday strategy is overrated and copying competitors makes you invisibleThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditLone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcasteCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show03:12 Hot take 1: Aggressive welcome series win06:06 Hot take 2: Subject lines aren't built for opens, they qualify09:51 Hot take 3: Higher unsubscribes can mean higher revenue14:28 Hot take 4: You're probably over-segmenting18:07 Hot take 5: Your abandoned cart flow is too long20:38 Hot take 6: A/B testing yourself into mediocrity24:21 Hot take 7: Send more often, segment smarter26:56 Hot take 8: Black Friday is overrated in its current form30:11 Hot take 9: Email design matters less than you think34:31 Hot take 10: Stop copying your competitors37:53 Final thoughts and what to comment below______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The 5-person retention team is on borrowed time.In this episode of Send It, Jimmy Kim and Chase Dimond go on the record about something a lot of brands have been quietly doing for the last 12 months. The traditional retention pod (manager, two coordinators, designer, copywriter, SMS specialist) is getting restructured out of existence. CFOs are running the math, AI got actually good, and the tooling caught up. The brands sending more email and making more revenue per send are doing it with one operator and a stack of AI tools, not a team of five. Jimmy and Chase walk through why this shift is happening, a day in the life of a 1-person operator, the four layer AI stack that makes it possible, and the five step playbook for becoming the operator brands actually want to hire in 2026.EP 84: The death of retention teams how to operate as a 1 person army in 2026 Here's what they cover:- The three forces (margin, AI quality, tooling) collapsing the traditional retention team- What the 1-person retention operator actually spends their time on- The four layer AI stack every solo operator should be running- The real risks of going solo (burnout, tunnel vision, creative sameness) and how to protect against them- The five step playbook for becoming the highest paid operator in retentionThank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditeCom 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://www.ecomemailcertified.com/______01:11 Podcast Intro and Hot Take02:25 Beauty Brand Case Study05:00 Why Teams Are Restructuring05:25 Force One Margin Pressure08:41 Force Two AI Quality Leap11:30 Force Three Tooling Maturity15:08 One Person Retention Role17:00 Four Core Jobs in 202620:24 Directing AI With Prompts22:52 Quality Control and Brand Voice26:05 AI Powered Performance Analysis28:17 Compensation and Job Security30:48 Brand Loaded AI Projects34:33 Production Tools And Design36:53 Analytics Feedback Loop40:03 One Person Team Risks41:17 Documentation And Backup Plans43:08 Quality Drift And QA45:04 Tunnel Vision And Pushback48:11 Creative Sameness Problem50:25 Burnout And Community52:00 Five Step Solo Playbook56:10 Final Recap And Wrap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimond\https://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Letting AI hit send on your email program is how brands lose their list overnight.In this episode of Send It, Jimmy Kim and Chase Dimond join Bernard Meyer, Omnisend's AI Operations Manager, to get on the record about what AI in email marketing actually looks like when it's working and where the fully autonomous fantasy falls apart. Brand voice drift, deliverability damage, and irreversible mistakes (mass suppressions, accidental deletions) are what happens when the human leaves the loop. The operators getting real lift are using AI as an assistant on skeletons, subject line variations, research, reporting, briefs, audits, and program analysis and feeding it real business data instead of asking it to hallucinate from scratch. Plus the three starter prompts every operator should run on day one.EP 83: How to Use MCP with your ESP (Step by step tutorial w/ prompts) Here's what they cover:- Why fully autonomous AI sending is the fastest path to brand voice damage and deliverability loss- The 7 high leverage tasks AI should actually be doing for your retention program- What MCP is, why it matters, and how it turns generic AI output into business-aware analysis- The three starter prompts (weekly snapshot, upsell segment recommendations, top-campaign pattern mining) that prove the stack works- The 10 prompt pack giveaway and how to put human-in-the-loop guardrails around every AI workflowThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditLone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcasteCom 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://www.ecomemailcertified.com/______02:37 AI as Tool Not Toy05:00 Three Practical Uses07:57 AI Hype to Ignore12:16 Real Time Savings16:09 Where Not to Trust20:26 Data Ceiling and MCP Intro23:01 Bernard Explains MCP28:41 MCP Setup and First Prompts30:40 Connect Omnisend in Claude32:06 Weekly Snapshot Prompt Demo36:08 Metrics That Matter Most38:50 Upsell Segments From Buyer Data41:12 When AI Gets Too Generic43:37 Repeat Winning Campaign Patterns47:48 Customer Data Access Guardrails51:36 Human in the Loop Framework54:30 Giveaway and Prompt Pack______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

A bad email gets ignored. A bad SMS gets you blocked.In this episode of Send It, Jimmy Kim and Chase Dimond unpack why SMS keeps falling flat for so many brands and walk through the copywriting formulas that actually convert. The problem isn't the channel, it's that nobody learned how to write for it. With only 160 characters up for grabs, every word has to earn its place, every hook has to land in the first three seconds, and every send has to feel worth interrupting someone's day for. Jimmy and Chase break down the three part structure every high-performing SMS follows, the specific formulas for abandoned cart, replenishment, VIP drops, and flash sales, and the AI prompts they use to write and tighten copy fast.EP 82: The 160-character masterclass: Writing SMS that actually convertsHere's what we're diving into:- Why SMS copywriting is a different skill than email and the four constraints that make it harder- The hook → value → action formula every high-performing SMS follows- Specific formulas for abandoned cart, replenishment, VIP drops, and flash sales- The AI prompts they use to generate, compress, and A/B test SMS copy- The frequency, segmentation, and testing rules that protect opt-out ratesThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditLone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcasteCom 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://www.ecomemailcertified.com/______02:57 Why SMS Is Different03:25 Space And AI Compression04:43 Context And Attention05:39 Intimacy And Tone06:43 Cost Frequency Segmentation08:02 Hook Value Action Framework10:48 Putting The Formula Together13:27 Abandoned Cart Playbook15:03 Replenishment Timing Texts16:27 VIP Early Access Drops17:06 VIP Drop Specifics17:56 Flash Sale Formula18:33 Mystery Discount Tests19:59 AI Prompts For SMS22:47 Prompt For Shortening24:02 AI Variations For Testing25:34 Replenishment Reminder Prompt27:21 Testing Framework Basics30:18 Common SMS Mistakes31:40 Advanced SMS Tips33:09 Final Recap And Wrap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

AI didn't fail you... your prompt did.In this episode of Send It, Jimmy Kim and Chase Dimond unpack why so many marketers are getting generic, unusable output from AI and walk through the prompt structure that fixes it. The problem isn't the tool, it's that nobody taught marketers how to talk to it. Most prompts are missing context, lack constraints, and leave AI guessing at the goal. They break down the four layer structure that turns vague requests into usable copy, then share the exact templates they use every day for subject lines, campaign ideation, body copy, brand voice training, SMS messages, and preview text. EP 81: The 4 layer prompt structure that fixes bad AI outputHere's what they cover: - The four layer prompt structure that turns lazy prompts into usable copy- The subject line and campaign ideation prompts that produce real variety, not filler- How to train AI on your brand voice using past winners and proven examples- The body copy, SMS, and preview text prompts they use every single day- The common prompt mistakes that produce bad AI output and how to fix themThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditWe're hitting the road! Join us for a private, half-day retention workshop coming to a city near you! Get tickets 20% off with ROADSHOW20:https://commerceroundtable.com/roadshoweCom 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://www.ecomemailcertified.com/______00:55 Welcome To Send It01:38 Prompts Matter Most03:02 Four Prompt Layers03:40 Layer One Context04:57 Layer Two Task05:37 Layer Three Constraints08:21 Layer Four Format09:29 Subject Line Prompts11:36 Train With Past Wins13:35 Curiosity Gap Testing14:48 Campaign Idea Prompts17:07 Pain Point Angles18:51 Pain Point Prioritization19:22 Seasonal Campaign Planner20:16 Remix Past Winners20:51 Email Body Copy Framework23:01 AI As Copy Editor24:28 Teach Brand Voice25:43 SMS And Preview Text28:26 Advanced Tips And Mistakes30:31 Edit And Test Outputs______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Your email program has problems. AI can find them in 5 minutes.In this solo episode of Send It, Chase Dimond walks through seven AI prompts that completely change how email marketers, agencies, and freelancers run their programs. Chase shows exactly how to audit an entire email setup, rewrite the flows that aren't working, build a 30 day calendar that mixes the right content, run a teardown of your competitors, and segment your list the right way. EP 80: The 7 AI prompts every email marketer needs Download all the prompts here >> https://ecomemailmarketer.com/ai-promptHere's what he covers:- The mock brand setup and the real numbers behind the audit example- How to interpret the audit output and pick the top three fixes to focus on- 7 AI prompts to audit, rebuild, rewrite, and optimize your systems- The AI rules every marketer needs to follow: editing, fabrication, and hype claimsThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditLone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcasteCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show02:33 Meet Dimond Apparel: the mock brand we're auditing today04:12 Prompt 1: the email program audit that ranks what's broken06:55 Walking through the audit output and the top three priority fixes09:58 Prompt 2: writing the actual flow emails with full subject line, preview text, and body copy12:05 Prompt 3: the draft scoring workflow that catches what's not strong enough to ship14:56 Prompt 4: writing subject lines that mix curiosity, urgency, social proof, and benefit16:37 Prompt 5: building a 30 day campaign calendar w the right content mix18:10 Prompt 6: running a competitor teardown to see where you stand in your category20:30 Prompt 7: building the right segments and matching content to each______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

A 14 email welcome series isn't a strategy... It's a slow goodbye.In this episode of Send It, Jimmy Kim and Chase Dimond break down why so many welcome series quietly underperform and walk through the four email framework that consistently turns subscribers into customers. They get into the psychology behind first-time buyers, the four questions every welcome series needs to answer, and the timing logic that unlocks conversions. If your welcome series is doing all the talking and none of the converting, go ahead and hit play.EP 79: Why most welcome series fail (and the 4 email framework that works)Here's what we're diving into:- Why long welcome series quietly tank your conversion rate and LTV- The "we, we, we" trap that makes brands talk past their new subscribers- Why leading with a discount trains the wrong buying behavior from day one- The four psychological questions every welcome series needs to answer- Why testing for LTV beats testing for conversion rate every time- The four mistakes that quietly kill welcome series performanceThank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=SenditLone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcasteCom 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://www.ecomemailcertified.com/______00:00 Welcome to the show02:51 3 Most common welcome series pitfalls08:56 The four email framework at a high level12:46 The tactical breakdown of the four email timeline13:26 Email 1: the welcome and how to deliver a quick win15:00 Email 2: the education email and when to send it16:41 Email 3: the recommendation email as a helpful guide18:41 Email 4: the social proof email as your closer21:27 The 7 to 10 day timing window and how to adjust it by category23:16 What to do when subscribers buy partway through the series24:23 How to test your welcome series the right way30:08 Recap of the four email framework and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

A 0.1% unsubscribe rate isn't the flex most marketers think it is.In this episode of Send It, Jimmy Kim and Chase Dimond take on one of the most misunderstood metrics in email marketing and make the case that obsessing over unsubscribes is quietly making your program worse. They walk through why playing it safe produces generic content, how a low unsubscribe rate can actually be a warning sign, and why the healthiest email programs are the ones willing to lose a few people every week. This one is a mindset reset for anyone who's ever flinched at an unsubscribe notification.EP 78: The unsubscribe paradox every marketer gets wrongHere's what they cover:- Why marketers are psychologically wired to fear unsubscribes- The difference between list size as a vanity metric & list quality as a revenue driver- What a healthy unsubscribe rate actually looks like in context- When unsubscribes are a signal you're doing something right- The three scenarios where an unsubscribe spike is a feature, not a bug- Four metrics that matter more than your unsubscribe rate- The benchmarks for when to celebrate, when to investigate, and when to panicThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show02:23 The unsubscribe paradox explained04:47 What a healthy unsubscribe rate looks like in 202608:32 The benchmarks for a healthy email program09:55 How fear of unsubscribes strips your brand of personality13:06 Scenario 1: taking a stance on something controversial14:19 Scenario 2: launching a new product or evolving your brand16:23 Scenario 3: intentionally cleansing your list with re-engagement18:57 The four metrics that matter more than your unsubscribe rate20:10 Why the best brands are willing to be polarizing21:39 The unsubscribe rate benchmark cheat sheet25:23 The hot take: unsubscribes are not the enemy, boring is25:48 Recap & final thoughts of the unsubscribe paradox______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The agency vs in-house debate has burned more brands than it has built.In this episode, Jimmy Kim and Chase Dimond break down the real decision framework behind one of the most loaded questions retention marketers, founders, and execs ask: should you hire an agency or build the team in-house? They get into when an agency actually makes sense, what you should never outsource, the hybrid model that works at scale, and the red flags that mean it's time to part ways.EP 77: Agency vs in house: when to hire, when to fireHere's what we're diving into:- What agencies are actually good at (and what they aren't)- The revenue threshold for hiring in-house vs outsourcing- Why strategy, customer insight, and brand voice should never leave the building- The hybrid model that works: in-house owns strategy, agency owns execution- When a project-based engagement beats a retainer- The five red flags that mean it's time to fire your agency- A four-question framework for making the call yourselfThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show02:15 What agencies are actually good at (and where they fall short)06:03 The case for hiring an agency08:43 Using an agency for one-off projects10:30 What you should never outsource13:18 Protecting your brand voice15:21 The hybrid model that actually works18:21 Red flags that mean it's time to fire them23:44 The gatekeeping knowledge problem24:24 A four-question framework to make the call27:09 Recap and final takeaways______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at:https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at:https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Creative used to be the bottleneck. It doesn't have to be anymore.In this episode of Send It, Jimmy Kim and Chase Dimond get tactical about how retention marketers can use AI to completely change how they produce email and SMS content. Not the vague "just use ChatGPT" advice, but the actual workflow, the brief structure, the editing process, and the quality control system that lets you go from a four hour campaign to a 30 minute one without your emails sounding like they were written by a robot. They also get honest about where AI still falls short and what it means for the future of retention marketing.EP 76: How to produce 5x more email and SMS content with AIHere's what they cover:- Why creative velocity is now a competitive advantage in retention marketing- The old workflow vs the AI workflow and where the time savings actually come from- The four layers where AI helps most: ideation, copywriting, personalization, and iteration- How to write a brief that gets AI to produce quality output instead of generic slop- The five step workflow from brief to send- The five point quality control checklist every AI draft should pass before it ships- How to train AI on your brand voice using past emails and screenshots- What AI still can't do: brand nuance, strategy, and deep customer insightThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show04:34 The old workflow and why it takes three to four hours per campaign06:18 How AI compresses the creative timeline10:13 The four layers where AI actually helps the retention workflow15:40 The five step workflow: start with a brief, not a blank prompt19:00 Idea generation and picking the best campaign angles22:07 Creating test variations from your edited base email22:44 How to prevent AI content from feeling robotic or generic25:52 The study, adapt, generate framework for better AI inputs30:40 What AI still can't do: brand voice nuance, strategy, and customer insight33:07 The future: mass personalization and content velocity at scale35:17 Recap of everything covered and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Bad tests don't just waste time. They send you in the wrong direction with confidence.In this episode of Send It, Jimmy Kim and Chase Dimond break down why traditional email testing is broken in 2026; and exactly how to fix it. Between Apple's Mail Privacy Protection inflating open rates and smaller segments making statistical significance harder to reach, the old way of testing leads to bad decisions disguised as data. This episode is the updated framework that actually works right now.EP 75: Creative testing that actually works in 2026Here's what they cover:-Why Apple MPP destroyed open rate as a reliable testing metric-The single biggest testing mistake brands are still making in 2026-The four layers of testing in order of impact; from positioning down to button colors-Three approaches to testing when your list is too small for traditional A/B splits-How to build a creative library that makes every future test smarter-The learning velocity mindset that separates the best email teams from everyone else-The HCE framework: hypothesis, control, evaluate-How to know when you actually have a winner and when it's just noiseThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show01:13 Why email testing got so much harder in 202604:05 How Apple MPP destroyed open rate as a reliable testing metric05:20 The metrics you should actually be testing against08:16 The one variable rule and why it matters10:25 Layer 1: Positioning - the highest leverage test most brands skip12:10 Layer 2: Structure - how the email is built and why it matters14:15 Layer 3: Creative - where most brands start but shouldn't15:21 Layer 4: Timing - when to send and why it matters for certain emails16:16 How to test effectively when your list is small20:45 Building a creative library that makes every future test smarter23:50 Learning velocity: why the best teams learn faster than everyone else27:58 The HCE framework: hypothesis, control, evaluate30:13 Recap of everything and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Retention isn't about technology. It's about human behavior. In this episode of Send It, Jimmy Kim and Chase Dimond get into the six psychology principles behind why people actually buy. From reciprocity to momentum, these are the human behavior triggers that the best retention programs are built on… and most brands aren't using any of them intentionally.If you've ever wondered why a technically good email still doesn't convert, this episode is going to change the way you think about every message you send.EP 74: Conversion psychology: 6 principles for retention marketersHere's what they cover:Why educational emails outperform promotional ones every timeThe urgency mistake that quietly trains your list to ignore youHow to diagnose and remove the friction killing your conversionsThe subject line technique that makes people feel compelled to openWhy the brands with the highest LTV sell identity, not just productsHow small actions like quizzes and reviews build toward a purchaseA simple checklist to audit any email before you hit sendA real replenishment email breakdown that hits five principles at onceThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show02:30 Principle 1: Reciprocity - give value before you ask06:50 Principle 2: Urgency - how to use it without losing credibility10:44 Principle 3: Friction removal - every email should remove at least one barrier15:20 Principle 4: Curiosity gaps - the subject line technique most brands get wrong19:55 Principle 5: Identity and belonging - sell who your customer wants to be25:30 Principle 6: Momentum - how small actions lead to big purchases28:27 A simple framework for applying all six principles to any campaign or flow29:45 A real email breakdown that hits multiple psychology principles at once30:43 Recap of all six principles and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Most brands switch ESPs and lose months of sender reputation in a single send. It doesn't have to go that way.In this episode of Send It, Jimmy Kim and Chase Dimond draw from over 1,000 personal ESP migrations to walk through the exact five step warmup framework brands should follow when switching platforms. From setting up a fresh sending domain to segmenting smarter than 90 day openers, this is the most practical deliverability episode we've done.EP 73: Our 5 step ESP migration warmup guideHere's what they cover:The three reasons most ESP migrations fail before they startStep 1: Setting up a fresh subdomain and authenticating SPF, DKIM, and DMARCStep 2: Configuring platform settings before sending a single emailStep 3: Connecting your store and rebuilding your flows the right wayStep 4: The segmentation strategy that separates buyers from prospects and why it mattersStep 5: Monitoring reputation by TLD and what to do when things go wrongWhen to hire help and what a managed migration actually costsThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to the show02:44 Why most ESP migrations fail before they even start05:55 Step 1: Setting up your new subdomain the right way09:26 Step 2: Configuring your platform settings before you send anything11:24 Step 3: Getting your store integration right15:06 Step 4: Building your segmentation strategy for warmup20:09 Step 5: How to sequence your daily sends during warmup24:34 The metrics that tell you your warmup is actually working28:31 What to do when deliverability drops mid warmup 30:06 How to diagnose a technical issue vs a burnt domain31:26 DIY migration vs working with a professional33:40 Recap of all five steps and final thoughts_____Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Discounts feel like the easy button. But every time you hit it, you're training your customers to wait for a sale… and slowly destroying your margins in the process.In this episode of Send It, Jimmy Kim and Chase Dimond break down the discount death spiral that most DTC brands are stuck in, and walk through five actionable frameworks for driving repeat purchases without ever needing to slash your prices. From loyalty programs that actually create status to content sequences that build confidence between purchases, this episode is a practical playbook for brands that want to compete on value; not price.Whether you're trying to wean customers off discounts or build a retention strategy from scratch, these frameworks work at any stage.EP 72: Why discounts are hurting your brand and what to do insteadHere’s what they’re digging into:- Why discounts borrow from future revenue and make the problem worse- Framework 1: Building a loyalty program with real value beyond points- Framework 2: Bundling products to sell outcomes, not just SKUs- Framework 3: Using exclusivity and early access to create urgency without discounting- Framework 4: Content micro-wins that build confidence and drive repeat purchases- Framework 5: Winning on convenience and service instead of price- What a no-discount retention calendar actually looks like week to week- The mindset shift from promo calendar to lifecycle marketingThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 The discount addiction nobody wants to talk about 02:35 The discount death spiral explained 05:10 Framework 1: Building a loyalty program with real value beyond points 10:43 Framework 2: Bundling to sell outcomes not just products 15:59 Framework 3: Using exclusivity and early access to create urgency without discounting17:56 The four step drop strategy broken down 20:36 The campaign sequence for an exclusive early access drop 22:01 Framework 4: Content micro-wins and why this is the most underrated retention lever26:23 Framework 5: Winning on convenience and service instead of price 31:13 What a no discount retention calendar looks like week to week 33:01 Recap of all five frameworks and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

What do owls, Drake, and 74,000 "exclusive" subject lines all have in common? They all showed up in email marketing data from 2025.In this episode of Send It, Jimmy Kim and Chase Dimond take a break from the serious stuff and dig into a fun data report from our partners at Omnisend. They review the emojis, celebrities, pop culture moments, holidays, animals, and overused cliches that dominated email campaigns throughout the year.The results are equal parts funny, surprising, and honestly pretty revealing about how email marketers think.Check out Omnisend’s full report here: https://www.omnisend.com/email-fun-facts-year-in-review-2025/?utm_source=SendIt&utm_medium=Promo Here's what we're getting into:The top 10 most used emojis in subject lines (the number one will surprise you)Which celebrities got name-dropped most - and why Drake topped the listThe TV shows and movies marketers referenced mostWhy owls beat dogs and cats as the most mentioned animalThe internet culture moments brands actually leaned intoMost mentioned holidays and whether the order matches the revenueThe overused cliches showing up in thousands of campaignsWhy "exclusive" appeared in over 74,000 campaignsThe oops and apology email trend - and how much of it was intentionalThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show03:44 The top 10 most used emojis in subject lines revealed08:43 The TV shows and movies marketers referenced most11:50 The most mentioned animal in email (it's not a dog or cat)15:54 Internet culture moments brands actually leaned into16:39 Protein, matcha, Stanley and the pop culture keywords of 2025 17:46 Viral moments that made it into email campaigns 20:12 How many brands actually talked about tariffs and politics21:59 The holiday calendar every email marketer is working from 23:51 The worst marketing cliches showing up in thousands of campaigns 25:14 Why "exclusive" is everywhere and how much of it is AI28:19 The oops and apology email - mistake or marketing tactic30:12 How 82% of marketers start their emails 31:43 Final thoughts and where to find the full report______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

There's a reason some brands keep growing and others plateau… and it usually shows up in their retention strategy first.In this episode of Send It, Jimmy Kim sits down with Feras Khouri, co-founder of New Standard Agency, to break down six things that 8 and 9-figure DTC brands consistently do in email and SMS that most brands overlook. Feras brings a rare perspective having scaled his own brand to 8 figures before building an agency that now works with some of the biggest names in DTC including AG1, Caraway, and New Era Caps. They also get into why email attributed revenue can actually be a warning sign, and what it really means when your year-over-year numbers start to slip.Whether you're at 7 figures or 9, the principles here are the same. The brands that win aren't just sending more emails. They're thinking about retention as a system.EP 70: 6 Retention habits of 8 and 9 figure DTC brandsHere's what we're diving into:-Why setting retention-specific goals changes everything (and why most brands skip this)- What "layer two metrics" actually means and why open rates aren't enough- How top brands look beyond email and SMS to drive retention across every channel- Using retention data to fuel acquisition and close the feedback loop- Why a strong product and honest internal feedback matter more than any campaign- How 8 and 9-figure brands rapidly test technology without getting distracted by the hype- The real role AI should play in a retention strategy (and what it can't replace)Thank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show02:00 Meet Our Guest: Feras's Khouri05:00 Does this apply to smaller brands? The 7-figure vs 8-figure question10:00 #1: Set retention-specific goals14:00 #2: Understand layer two metrics 17:00 #3: Look beyond email and SMS 22:00 #4: Use retention for acquisition27:00 #5: Create an internal feedback loop 37:00 #6: Rapidly test technology 41:00 Building a brand brain with AI vs. using AI to replace human thinking44:00 Wrap up, where to find Feras, and final thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

AI is everywhere in email marketing… but is it actually workingIn this episode of Send It, Jimmy Kim sits down with Filip Pejic, Co-Founder of Bedford & Pearly, to talk about how smart email marketers are actually embracing AI right now (and where it's still falling flat). Plus, Filip shares three real campaign ideas that are driving serious clicks and engagement for brands today.From training entire agency teams on AI design tools, to why ChatGPT is making copywriters lazier, to the Super Bowl halftime sale that became a client's biggest revenue hour ever; this episode is full of honest takes and actionable ideas.EP 69: How to embrace AI as an email marketer + 3 hot click tipsHere's what we're diving into:- How Filip's agency runs weekly AI training sessions with their whole team- Why AI copywriting is creating a "degradation of ideas" + what to do instead- The flowchart email concept that's unlocking click engagement for brands- How a 60-minute Super Bowl halftime sale drove record-breaking revenue- The nostalgic Valentine's Day campaign that crushed for an apparel brand- Why timely, unexpected promotions beat perfectly scheduled campaigns- Jimmy and Filip's take on where email is headed as AI agents emergeThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Why Most Brands Are Using AI Wrong01:40 From Finance to Founder: How Phil Built His Edge07:30 The 8-Figure Brand Advantage (And What Smaller Brands Miss)10:39 Where AI Actually Saves Time (Process + Design Workflows)12:58 The Truth About AI Copy: Brainstorming vs. Original Thinking15:02 Why Voice, Hooks, and Angles Still Win16:42 The Real Differentiator in 2026: Taste + Ideas19:43 Using Gemini to Align Copy and Design Faster20:41 The ESP Data Trap (And Why History Can Hurt You)21:46 The Power of “In-Between” Campaigns (Beyond Sales)24:05 Why Retention Still Needs Humans25:11 Click Strategies That Don’t Rely on Discounts26:24 Super Bowl SMS Drop + Valentine’s Click Case Study33:56 Will We Be Emailing AI Agents? The 5–10 Year Outlook37:16 Final Takeaways: What Actually Matters______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Acquisition is harder. CAC keeps climbing. Attribution feels like guesswork.The brands still growing profitably are not “sending more” to fix it. They’re building retention systems that move customers forward, one step at a time.In this episode of Send It, Jimmy Kim and Chase Dimond teach a practical 8-step retention framework built from real brand work and Omnisend benchmark data. You’ll also get a downloadable worksheet to map your customer journey, audit your lifecycle gaps, and turn retention into something repeatable.This is not a “run more campaigns” episode. It’s how to build a retention engine that makes revenue more predictable.Download the worksheets here: https://cdn.prod.website-files.com/6735048599b05e098e178c8f/6952c64d53f794174c3fa62d_Retention%20Redefined%20Worksheets.pdf Access Omnisends full report here: https://www.omnisend.com/resources/reports/2026-ecommerce-marketing-report/?utm_source=SendIt&utm_medium=Promo EP 68: A practical framework for profitable email and SMS in 2026Here's what we're diving into:- The modern customer journey most brands ignore after first purchase, and how to fix it- How segmentation should mature from basic to predictive- Strategy for making email and SMS work in tandem- How to leverage AI while maintaining the human touch to build trust- The 8 automations that form a real retention engine- The 2026 retention scorecard- A simple 90-day plan to implement the frameworkThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show04:04 The Importance of Retention Marketing09:58 The Modern Customer Journey15:06 Effective Segmentation Strategies18:37 Channel Pairing: Email and SMS21:05 Leveraging AI in Retention Marketing25:11 Personalizing Messages at Scale26:52 Optimizing Key Flows for Retention28:35 Advanced Retention Strategies32:58 Metrics That Matter in 202639:35 Implementing a 90-Day Retention Plan42:19 Final Thoughts and Resources______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Open rates are inflated. Clicks are misleading. And inbox algorithms don’t reward surface-level engagement anymore.In this episode of Send It, Jimmy Kim and Chase Dimond break down why traditional email and SMS metrics are failing eCom teams; and what you should be tracking instead as inbox rules, privacy changes, and AI filtering reshape how messages get seen.Optimizing for opens and clicks can feel productive, but it often leads brands to make confident decisions based on incomplete signals. This episode introduces a modern measurement framework built around real behavior, intent, and revenue impact (not vanity metrics).EP 67: The new definition of engagement (and the metrics that actually matter) Here's what we're diving into:- Why open rates are inflated, unreliable, and no longer decision-worthy- How inbox providers now use engagement as a visibility signal- The 4-layer engagement stack top brands are adopting- Which metrics actually prove retention impact to leadership- How to rethink attribution without chasing “perfect” numbers- What to move to the top of your KPI dashboard (and what belongs at the bottom)Thank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show02:21 Redefining Engagement Metrics02:54 Impact of Privacy and AI on Email Marketing04:37 New Requirements from Google and Yahoo05:43 Gmail's Algorithm and Engagement07:38 The Shift to Quality Over Quantity11:49 Building a Real Engagement Stack14:50 Key Email Metrics15:23 SMS Metrics Overview16:04 Customer Behavior Insights17:24 Business Outcomes Metrics20:05 Challenges in Attribution25:01 Actionable Steps for Improvement28:32 Conclusion and Wrap-Up______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Most brands only segment by openers and VIPs… then wonder why email performance stalls.In this episode of Send It, Chase Dimond and Jimmy Kim dive into 12 powerful email and SMS segments that go beyond the basics and actually boost conversions, protect margins, and reduce fatigue. These aren’t theory; they’re tried and true segments top DTC brands use to send smarter.You’ll learn how to segment based on intent, behavior, timing, and risk; so every message feels more personal, more relevant, and more profitable. Whether you’re scaling a list or trying to squeeze more ROI from your existing subscribers, this framework will help you unlock smarter strategy and cleaner results.EP 66: 12 Unusual segments that drive serious eCommerce revenueHere's what we're diving into:• How to identify discount rejectors, promo-only buyers, and risky first-time customers• What to actually send each segment (not just how to build them)• The 3 things every good segment should change in your marketing• How to avoid over-discounting and protect your brand's positioningThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show04:29 Why Microsegmentation Matters for Your Business09:33 12 Unusual Segments for Revenue Growth09:46 Discount Rejectors11:25 Product Loyalists 13:05 Risky First-Time Buyers15:09 High AOV, Low Frequency Buyers16:55 Engagement Only Buyers19:02 Seasonal Only Buyers21:58 Promo Only Buyers23:43 Reactivating Recently Lapsed High-Value Buyers25:26 Engaging Multi-Category Explorers26:56 Converting Subscription-Adjacent Buyers29:28 Recognizing and Rewarding Brand Advocates33:39 Understanding and Targeting Silent VIPs35:37 Tips for Implementing Segmentation Strategies40:27 Recap and Final Thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The biggest mistake most brands make? They think retention starts after the first sale.In this episode of Send It, Jimmy Kim and Chase Dimond break down why the real retention window starts the moment someone joins your list (not when they buy). You’ll learn how to design your first 45-day subscriber journey to build trust, deliver micro-wins, and turn subscribers into repeat customers. Plus, we break down habit loops, lifecycle stages, and the overlooked “repeat trigger window” that keeps customers coming back.EP 65: Why the first 45 days matter more than the first purchaseHere's what we're diving into:- The 4 critical stages in a subscriber’s first 45 days- How to create emotional “micro-wins” that build brand trust- Using habit loops to make your product part of the customer’s routine- The importance of timing in repeat purchase messaging- Real brand examples and lifecycle strategy breakdownsThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show03:02 The Critical First 45 Days of a Subscriber's Life08:08 Breaking Down the First 45 Days into Stages16:00 Creating Micro Moments and Micro Wins20:27 Understanding Habit Loops: Cue, Routine, Reward23:00 Building Habits Through Email and SMS26:37 The Importance of Repeat Trigger Windows29:26 Proactive vs. Reactive Messaging31:51 Calculating and Utilizing Repeat Trigger Windows34:05 Bringing It All Together: A Cohesive Strategy36:28 Conclusion and Recap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

We got early access to Omnisend’s 2025 ecommerce report and the numbers will change how you think about your email and SMS strategy.Based on 41 billion+ messages from over 160,000 ecommerce brands, this isn’t a survey or projection; it’s real customer behavior data. What did we learn? Most brands are optimizing for the wrong things.In this episode, Jimmy and Chase break down the data that proves automations destroy campaigns on performance, why transactional emails are secret revenue engines, and how top brands quietly grew 200% while others shrank.Grab Omnisend’s full report here: https://www.omnisend.com/2026-ecommerce-marketing-report/?utm_source=SendIt&utm_medium=Promo EP 64: What we learned from 41 billion emails sent in 2025Here's what we're diving into:- Why your campaign-heavy strategy is missing out on potential gains- The underrated flow that beats abandoned cart in both revenue and conversions- How to turn transactional emails like shipping updates into revenue-generating touchpoints- When SMS actually converts (and when it’s just wasting your send)- The 5 automations you should prioritizeThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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/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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show02:17 Key Insights from the Report07:54 Transactional Emails: Untapped Potential12:24 Preparing for Q4: Strategies and Insights16:44 The Role of SMS in Marketing17:57 SMS Campaigns vs. Automations21:31 Optimizing SMS for eCom24:34 Order Growth Insights26:22 Global eCom Trends27:30 Fundamentals of Automation35:35 Campaigns vs. Automations39:22 Final Takeaways and Recommendations______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Struggling with retention but not sure what’s broken?In this episode, Jimmy Kim and Chase Dimond walk through their 7-part retention audit framework used to diagnose DTC brands in 60 minutes or less.Whether you’re an agency, operator, or founder, this episode breaks down how to find revenue leaks, fix deliverability, improve your flows, and benchmark your lifecycle strategy against the best in the game. You’ll learn how to check your data plumbing, uncover hidden issues in your segmentation, and rebuild an email + SMS program that actually works.EP 63: The retention audit: How to diagnose any brand in 60 minutesHere's what we're diving into:- The 7-part retention audit framework- What to check when open rates drop- How to evaluate deliverability, infrastructure, and attribution- Which flows every DTC brand should have (and most don’t)- High-impact segmentation strategies- The biggest mistakes brands make in messaging, offers, and timingThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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://omnisend.com/senditeCom 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://www.ecomemailcertified.com/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://inboox.ai/______00:00 Welcome to The Show03:12 Retention Audit Framework Overview04:17 Data Infrastructure: The Foundation08:51 Deliverability and List Quality15:37 Lifecycle Automation: Maximizing Revenue20:17 The Importance of Timely Replenishment23:09 Effective Segmentation Strategies26:43 Crafting Mobile-Optimized Emails31:08 Enhancing Customer Experience Beyond Emails35:47 Analyzing Metrics for Better Retention37:56 Final Thoughts and Recap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Most brands obsess over open rates, but ignore the most misleading metric in their dashboard: clicks.In this episode, Jimmy Kim and Chase Dimond break down the truth about email and SMS click tracking. From accidental taps to bot activity to real buyer intent, not every click means the same thing. But most ESPs lump them all together, inflating your metrics and misleading your decisions.Jimmy and Chase share a clearer framework for identifying click quality, improving attribution, and optimizing for real engagement; not just vanity numbers.Plus, we introduce eClickTrack, our new link-tracking tool built for ecommerce brands who want to see real, human engagement, not bots.EP 62: The secret behind the click and why click tracking is so importantHere's what we're diving into:- The 4 types of clicks (and how to spot them)- How bot clicks inflate your metrics (and how to fix it)- The psychology behind high-value clicks: curiosity, urgency, value, and design- What your ESP isn’t telling you (and how to get better attribution)- A 6-part playbook to improve your click quality and conversionsThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditeCom 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-senditExplore 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______00:00 Welcome to The Show02:08 Deep Dive into Clicks05:04 Types of Clicks Explained07:45 Driving High-Quality Clicks13:12 Challenges with Click Data15:39 The Problem with Bot Clicks17:01 Common Email Marketing Mistakes19:58 Key Features of E Click Track26:06 Optimizing Click Quality in Email Campaigns28:59 Final Thoughts and Recommendations______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at:https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

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 2026Here'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 KPIsThank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditeCom 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-senditExplore 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______00:00 Welcome to the Show04:26 Cohort Yield vs. Campaign Revenue06:44 Flow Weight vs. Campaigns10:32 Strategic Use of SMS13:13 Importance of Deliverability15:32 Predictive Segmentation17:55 Creative Testing: Emotion vs. Design18:13 Behavioral Copy Strategies for Marketers20:40 The Future of Preference Centers23:37 Profit Accountability for Marketers25:27 Retention Marketers and Replenishment Control29:13 Job Security Tied to Returning Customers31:15 The Role of AI in Marketing34:59 Conclusion and Final Thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Gmail just rolled out the biggest inbox overhaul in years and it’s about to change how every ecommerce brand sends email.In this episode, Jimmy Kim and Chase Dimond break down the new Gmail features that are shaking up deliverability, unsubscribe rates, and how messages show up in the Promotions tab.They cover everything from the new Manage Subscriptions view (which ranks senders by frequency and makes unsubscribing easier than ever) to Postmaster Tools v2 and Google’s new compliance enforcement rules for bulk senders.EP 60: Gmail’s new rules: What every email marketer needs to knowHere's what we're diving into:- The 3 Gmail updates every marketer needs to understand- How frequency and engagement now determine inbox visibility- What the new “Purchases” view means for transactional emails- How Gmail’s smarter Promotions tab changes your send strategy- The truth about Postmaster Tools v2 and new compliance rules- How to audit your setup before November 2025 enforcement kicks inRead more about the deliverability report: https://e.eemtrk.com/gmail-changes-senditThank you our friends at Omnisend, eCom Email Certified, and Kintsugi for sponsoring the podcast!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://eemtrk.com/omnisend-senditeCom 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-senditExplore 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______00:00 Welcome to The Show00:53 Overview of Gmail Changes03:47 Gmail's Managed Subscription View11:27 Gmail's New Purchase View17:42 Promotions Tab Overhaul19:10 Gmail's New Relevance Ranking System22:08 Strategies for Improving Email Engagement26:37 Technical Changes in Gmail's Postmaster Tools29:24 Compliance and Enforcement for Bulk Senders36:05 Summary and Key Takeaways______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

BFCM 2025 didn’t play out the way anyone expected. In this special report, Jimmy Kim and Chase Dimond break down what actually happened, why it happened, and what it means for ecommerce brands heading into 2026.Pulling fresh data from Omnisend, Shopify, Adobe Analytics, and hundreds of brand conversations, they unpack the consumer behavior, sales trends, offer performance, inbox shifts, SMS usage, and emerging AI-driven shopping habits that defined this year’s results.Jimmy and Chase also share real examples of what worked, what flopped, and how brands can approach 2026 with smarter pre-launch planning, tighter segmentation, stronger waitlists, better bundling, and more intentional offer design.EP 59: The real lessons from Black Friday + Cyber Monday 2025Here's what we're diving into:- Why Black Friday still dominated, even with earlier offers- Why Cyber Monday surged for many brands- How offer fatigue and creativity collapse hurt performance- What Omnisend data showed about AOV, flow revenue, and list behavior- How AI-driven shopping and inbox filtering changed resultsThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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-senditExplore 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______00:00 Welcome to The Show01:15 The Importance of BFCM Buyers02:42 Maximizing Post-BFCM Engagement03:10 Understanding BFCM Buyer Behavior06:52 Effective Follow-Up Strategies10:12 Tactical Campaign Ideas20:33 Key Metrics to Track23:44 Conclusion and Final Thoughts______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Most brands blow their budget on BFCM and then ghost their best customers.In this episode of Send It, Jimmy Kim and Chase Dimond break down what happens when you go silent after Black Friday and how to fix it. You’ll learn how to turn high-intent, one-time buyers into loyal, high-LTV customers using a proven 4-stage retention strategy.They share the campaigns to send, the exact follow-up timing, and 5 post-BFCM metrics to track to keep your Q4 profitable after the sale.EP 58: Don’t go silent after BFCM (Here’s what to send next)Here's what we're diving into:- Why second purchases are the key to post-BFCM profitability- The biggest mistake brands make after Black Friday- A 4-stage post-purchase flow: onboarding, education, bridge offer, nurture- 5 plug-and-play campaigns to send right now- The metrics that matter: time-to-second-purchase, flow conversion, and moreThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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-senditExplore 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______00:00 Welcome to The Show03:56 The Importance of Recency, Intent, and Volume07:37 Common Mistakes Brands Make Post-BFCM12:50 Stage One: Onboarding Emails14:16 Stage Two: Educational Content15:29 Stage Three: The Bounce Back Offer17:40 Stage Four: Long-Term Nurture18:49 Effective Email Campaigns23:48 Metrics to Track Post BFCM28:56 Final Recap and Closing Remarks______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

What's the perfect email cadence? Daily, weekly, or just when you have something to say?In this episode, Jimmy and Chase break down the pros and cons of different email frequencies (daily sends, weekly campaigns, and launch-only strategies) and help you figure out what cadence is right for your brand.They share real examples, revenue-impacting data, and a step-by-step framework to test and dial in your ideal email frequency; without burning your list or obsessing over unsubscribes.EP 57: How often should you really email your list?Here's what we're diving into:- Daily vs. weekly vs. campaign-based sending (and what actually works)- A real-world test: 2 emails/week vs. 5 emails/week (+70% revenue)- Why open rates and unsubscribes matter less than you think- 5 factors that determine the right cadence for your brand- How to segment your list by frequency without overwhelming subscribers- The “steady + burst” strategy top brands use to scale email without burnoutThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show04:40 Pros and Cons of Daily Emails07:00 Who Should Send Weekly (and Why)08:35 Campaign-Only Sending: When It Works10:20 Real-World Cadence Test: 2x vs 5x Per Week14:00 Unsubscribes, Open Rate Myths & What Actually Drives Revenue18:40 5 Factors That Determine the Right Cadence22:00 Segmenting by Frequency (VIPs vs Unengaged)23:15 Smart Suppression & Total Email Count25:00 Red Flags That You're Over-Sending28:30 Your Email Cadence Optimization Playbook______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at:https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The biggest week in ecommerce is the one everyone forgets.In this episode, Jimmy Kim and Chase Dimond break down one of ecommerce’s best-kept secrets: Q5. The week between Christmas and New Year’s that quietly drives massive revenue for brands that don’t go dark. Most brands shut off campaigns after BFCM, but consumers aren’t done buying. They’ve got gift cards, return credits, and “treat yourself” energy. That’s your big window.Jimmy and Chase reveal exactly how to plan, message, and automate your Q5 campaigns so you can capture the easiest money of the year while your competitors are on vacation.EP 56: The secret quarter most brands ignore (Q5)Here's what we're diving into:- Why Q5 works (returns, gift cards, and self-gifting behavior)- 4 winning campaign angles: encore sale, gift card push, self-care, flash sale- How to message Q5 differently from BFCM- The ideal Q5 cadence for email + SMS (with examples)- How to automate everything before Dec 26 and still cash in- What NOT to do (hint: stop copy-pasting your Black Friday sale)Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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-senditExplore 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______00:00 Introduction to Q5: The Secret Fifth Quarter02:36 Understanding Q5: Why It Matters\04:12 The Q5 Playbook: Strategies for Success10:32 Promotional Strategies for Q515:38 Flash Sales and What Not to Do During Q517:55 Meeting Customers Where They Are18:24 Creative Angles for Post-Holiday Marketing20:45 Optimizing Email and SMS Cadence25:21 Automating Q5 Campaigns30:21 Q5 Checklist and Best Practices33:10 Final Thoughts and Promotions______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Ever wondered what Jimmy and Chase are up to behind the scenes?In this episode, the duo reflect on their first year of partnership and pull back the curtain on what they’re building next… two new tools designed to change the way ecommerce brands do retention marketing.From analyzing millions of emails to redefining attribution, they break down how Inboox.ai and eClickTrack are solving the biggest problems email and SMS marketers face today: lack of visibility, disconnected data, and shallow insights.Pull up a seat because Chase and Jimmy are breaking down their roadmap for the next wave of retention marketing tools.EP 55: Why we’re betting big on retention toolsHere's what we're diving into:- The vision behind Inboox.ai and why it’s the “search engine” for ecommerce emails- How eClickTrack will give marketers real attribution clarity without iOS blind spots- Lessons from scaling media, agencies, and SaaS under one retention brand- Why retention marketing needs smarter data, not louder campaigns- The future of ecommerce tech stacks in a post-BFCM worldThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 — Intro + Behind the Scenes02:00 — The Vision: Building the Future of Retention Marketing05:00 — The Origin of eClickTrack10:15 — Solving Bot Clicks + Real Attribution13:00 — Use Cases: Creators, Brands, and Agencies19:45 — Introducing Inboox.ai23:45 — The AI Breakdown: Email Analysis Engine26:30 — Who It’s For30:30 — Pricing + Agency Collaboration Tools32:00 — Closing Thoughts + Next Steps______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

What if 80% of your email revenue comes from just 20% of your effort?In this episode, Jimmy Kim and Chase Dimond unpack the real data behind ecommerce email performance; revealing the flows, segments, and campaigns that actually move the needle (and the ones you can delete today).They’ll show you how to stop over-engineering your automations, focus on the top-earning flows, and simplify your email strategy to drive more revenue with fewer sends. If you’ve ever felt overwhelmed by 47 flows, endless A/B tests, or bloated lists, this episode is your reset button.EP 54: The 80/20 of Email Revenue: How to Double Your ROI by Doing Less Here's what we're diving into:- The 3 flows that drive 60–80% of automated revenue (and how to optimize them)- The segments that matter: VIPs, one-time buyers, and engaged subscribers- Why your welcome and sunset flows don’t deserve your energy- Campaign types that convert - and how to balance promo vs. content sends- The metrics that matter in 2025 (hint: it’s not open rates)- How to cut 50% of your email workload and still grow fasterThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show02:14 The 80/20 Rule in Email Marketing04:24 Key Revenue-Generating Email Flows10:13 The Power of Post-Purchase Flows12:21 The Importance of Browse Abandonment13:28 Overrated Email Flows16:16 High-Value Segments in Email Campaigns21:15 Segments That Don't Matter: Avoiding Common Pitfalls24:31 Effective Campaign Strategies28:15 What Not to Send: Avoiding Common Mistakes35:47 The 80/20 Rule: Simplifying for Success______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Didn’t plan your BFCM campaigns yet? You’re not alone (and it’s not too late).In this episode, Jimmy Kim and Chase Dimond walk you through a flexible, week-by-week playbook for Black Friday and Cyber Monday that any ecommerce brand can execute… fast.They break down how to start strong, end smarter, and turn Q4 buyers into long-term customers using email and SMS. From offer strategy to channel orchestration, this episode is packed with tactical advice for brands who want to finish the year profitably without burning out their list.EP 53: It’s Not Too Late: Your 2025 Black Friday & Cyber Monday Email + SMS PlaybookHere's what we're diving into:- How to choose your BFCM launch lane: Early Bird, Core Week, or Late Burst- 4 proven offer types that drive margin, not just clicks- The 3-step pre-launch flow to warm your list before Black Friday- How to plan your “encore” for post-sale revenue lift- Why Cyber Monday should be your retention moment, not a rerun- Best timing for email + SMS and how to orchestrate both togetherThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show01:36 Introduction to the Black Friday Cyber Monday Playbook03:06 Mindset Shift: BFCM as a Season03:59 Flexible Start Framework for BFCM06:31 Offer Archetypes and Strategies15:13 The Role of Email and SMS in BFCM18:59 Aligning BFCM with Business Goals20:19 Final Thoughts and Recap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

What’s really happening in email, SMS, and push marketing this year? In this data-packed episode, Rytis Lauris (CEO & Co-Founder, Omnisend) joins Jimmy Kim and Chase Dimond to break down performance insights from over 150,000 ecommerce brands - covering 41 billion emails, 694 million SMS, and 869 million push notifications.They dig into the numbers shaping 2025: open and click trends, conversion rates, automation performance, and the rise of SMS and push as key retention channels. Whether you’re planning your Q4 strategy or want to understand how automation is driving disproportionate revenue, this session gives you the clarity and tactical takeaways you need.EP 52: 2025 Email & SMS So Far: Data & Insights with OmnisendHere's what we're diving into:- Why open rates are falling in automations but rising in campaigns- What the latest data says about click-throughs, AOV, and unsubscribe trends- How automations drive 37% of orders while making up just 2% of sends- The new SMS benchmarks - and why it’s outperforming during high-urgency moments- Why push notifications are the most underused (and profitable) free channel in ecommerceThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show03:10 Data Insights and Analysis04:56 Email and SMS Marketing Trends09:07 Click Rates and Unsubscribe Trends14:04 Average Order Value and Conversion Rates19:39 Increasing Automation in Marketing21:43 Email Click-to-Conversion Rates23:56 The Rise of SMS Marketing32:16 Push Notifications: The Overlooked Channel37:13 Final Thoughts and Q4 Strategies______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Apple’s iOS 26 update just changed the game for retention marketers. With link tracking stripped, device signals scrambled, inflated open rates, and SMS promos getting buried in “Unknown Senders,” the old email and SMS playbooks won’t cut it anymore. In this episode, Jimmy Kim and Chase Dimond unpack exactly what’s different, why it matters, and how ecommerce brands can adapt ahead of Black Friday and Cyber Monday. They break down what these changes mean for attribution, campaign visibility, and KPIs. Plus, they share the tactical fixes you can implement now to keep your flows performing.EP 51: iOS 26 Explained: What Apple’s New Update Means for Email & SMS MarketersHere's what we're diving into:- iOS 26 changes: link tracking protection, fingerprinting defenses, noisy open rates, SMS filtering- How attribution breaks (and how to fix it with server-side tracking + incrementality tests)- Becoming a “known sender” on SMS: two-tap opt-ins, first-message replies, vCard saves- KPI shifts: stop celebrating opens; track RPR/RPS, replies, and 30–90 day lift- Lifecycle plays that still work: welcome, abandoned cart, back-in-stock, VIP promosThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show03:11 Deep Dive into iOS 26 Changes05:55 Link Tracking Protection Explained08:53 Device Fingerprinting Defenses09:35 Email Engagement Distortion10:52 SMS Filtering and Placement14:00 Impacts and Future Strategies16:50 Strategies for Retention Marketers26:23 Multi-Channel Marketing Insights27:43 Final Thoughts and Recommendations______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The average shopper gets 121+ emails a day… and during peak seasons like Black Friday, it can feel like 200+. Most brands try to compete by sending even more emails, which just adds to the clutter. The smartest marketers take the opposite approach. In this episode of Send It!, Jimmy Kim and Chase Dimond break down how to cut through inbox chaos with smarter timing, distinctive creative, and emails that people actually want to open.EP 50: Overcoming Inbox Overload: Stand Out Strategies for Competitive Markets in eCommerceHere's what we're diving into:- Use off-peak send times and behavioral data to beat inbox congestion- Design standout creative that breaks “banner blindness”- Lead with value-first content that customers look forward to- Personalize beyond the first name with lifecycle and behavior-driven tactics- Build exclusivity and community that transforms your list into a membershipThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show03:45 Strategic Timing and Send Optimization09:13 Creative Differentiation in Email Marketing16:53 Leading with Value and Educational Content23:12 The Power of Educational Emails24:32 Advanced Personalization Strategies33:13 Creating Exclusive Community Experiences37:54 Final Thoughts and Key Takeaways______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at:https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

How do you go from writing subject lines to running one of the fastest-growing retention agencies in ecommerce? In this episode of Send It!, Jimmy Kim and Chase Dimond sit down with Eric Rausch, co-founder of New Standard, the retention agency behind brands like AG1, New Era, Rugable, Caraway, Bylt, and more.Eric shares his journey from starting as an in-house email marketer to building an agency that helps scale household names. He opens up about the realities of agency life (the good, the bad, and the late-night Black Friday calls) and what it really takes to succeed in retention marketing today.EP 49: From Email Marketer to Retention Agency Co-Founder feat. Eric RauschHere's what we're diving into:- How Eric went from brand-side email marketer to agency founder- The mindset shift needed to scale from KPIs to strategy- What separates senior retention talent from entry-level marketers- Top KPIs his team tracks: first-time purchase rate, repeat rate, subscription churn, and revenue growth- Hard truths about agency life (and why it’s not for everyone)- Black Friday + Q5 retention strategies that actually move the needle- Why direct mail and app pushes are underrated weapons in Q4Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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______00:00 Welcome to The Show02:13 Guest Introduction: Eric Rausch03:20 Eric's Journey in Email Marketing06:56 Building a Successful Retention Agency10:46 Key Performance Indicators (KPIs)14:02 Black Friday/Cyber Monday Strategies16:45 Advice for Aspiring Agency Owners24:43 Understanding Your Ideal Client Profile (ICP)25:37 The Realities of Starting an Agency27:14 Preparing for Black Friday and Cyber Monday37:37 Exploring Alternative Channels for Black Friday40:00 Conclusion and Social Media Plugs______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Most brands still treat email and SMS like broadcast tools. They send promotions, track clicks, and hope for the best. But the smartest operators are shifting to conversational commerce, where every message invites a response, every reply provides insight, and every interaction strengthens the customer relationship.In this episode of Send It!, Jimmy Kim and Chase Dimond share the frameworks top ecommerce brands are using to transform email and SMS into high-performing, two-way channels. From reply-driven email campaigns to consultative SMS flows and integrated customer service, they break down how to build conversations that lead to higher engagement, more conversions, and stronger retention.EP 48: The Rise of Conversational Commerce: Turning Email & SMS into Two Way ChannelsHere's what we're diving into:- Reply-driven emails that spark genuine customer dialogue and insights- SMS flows that drive engagement and sales through natural back-and-forth- Integrating customer service directly into email and SMS- Using conversational feedback loops to build community and loyalty- Turning consultative conversations into higher conversions and repeat purchasesThank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom 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-senditJoin Chase, Jimmy and 500+ eCom marketers and operators at Commerce Roundtable San Diego this September! Featuring keynote speakers like Gary Vee, Ezra Firestone, Taylor Holiday and more. Secure your spot before it sells out a third year in a row! Use code SEND IT for 25% off https://eemtrk.com/sendit-crsd-25 ______00:00 Introduction to Conversational Commerce03:40 Strategy 1: Reply-Driven Email Campaigns09:46 Strategy 2: Building SMS Conversational Flows17:10 Strategy 3: Integrating Customer Support into Email and SMS23:43 Strategy 4: Building Relationships Through Support24:54 Strategy 5: Collecting Feedback and Building Community30:47 Strategy 6: Optimizing Sales Conversations38:46 Summary and Key Takeaways______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!