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9K to 30K🎙 Daily cadence·76 episodes·Last published 3d ago - Monthly Reach
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Recent episodes
EP 83: How to Use MCP with your ESP (Step by step tutorial w/ prompts)
Jun 2, 2026
Unknown duration
EP 82: The 160-character masterclass: Writing SMS that actually converts
May 26, 2026
Unknown duration
EP 81: AI prompt engineering for email marketers: The templates that actually work
May 19, 2026
Unknown duration
EP 80: The 7 AI prompts every email marketer needs
May 12, 2026
Unknown duration
EP 79: Why most welcome series fail (and the 4 email framework that works)
May 5, 2026
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/2/26 | EP 83: How to Use MCP with your ESP (Step by step tutorial w/ prompts) | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 5/26/26 | EP 82: The 160-character masterclass: Writing SMS that actually converts | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 5/19/26 | EP 81: AI prompt engineering for email marketers: The templates that actually work | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 5/12/26 | EP 80: The 7 AI prompts every email marketer needs | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 5/5/26 | EP 79: Why most welcome series fail (and the 4 email framework that works) | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 4/28/26 | EP 78: The unsubscribe paradox every marketer gets wrong | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 4/21/26 | EP 77: Agency vs in house: When to hire, when to fire | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 4/14/26 | EP 76: How to produce 5x more email and SMS content with AI | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 4/13/26 | EP 75: How to A/B test emails when the old playbook is broken | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 3/31/26 | EP 74: Conversion psychology: 6 principles for retention marketers | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
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| 3/24/26 | EP 73: Our 5 step ESP migration warmup guide | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 3/17/26 | EP 72: Why discounts are hurting your brand + what to do instead | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 3/10/26 | EP 71: The funniest things email marketers did in 2025 | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 3/3/26 | EP 70: 6 Retention habits of 8 and 9 figure DTC brands | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 2/24/26 | EP 69: How to embrace AI as an email marketer + 3 hot click tips | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 2/17/26 | EP 68: A practical framework for profitable email and SMS in 2026 | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 2/10/26 | EP 67: The new definition of engagement (and the metrics that actually matter) | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 2/3/26 | EP 66: 12 Unusual segments that drive serious eCommerce revenue | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 1/27/26 | EP 65: Why the first 45 days matter more than the first purchase | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 1/20/26 | EP 64: What we learned from 41 billion emails sent in 2025 | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 1/13/26 | EP 63: The retention audit: How to diagnose any brand in 60 minutes | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 1/6/26 | EP 62: The secret behind the click and why click tracking is so important | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 12/30/25 | EP 61: Here's what AI says about retention marketing in 2026 | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 12/16/25 | EP 60: Gmail’s new rules: What every email marketer needs to know | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
| 12/9/25 | EP 59: The real lessons from Black Friday + Cyber Monday 2025 | 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 hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information! | — | ||||||
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