Send It!

Send It!

The SendIt Podcast, hosted by email marketing experts and veterans Jimmy Kim and Chase Dimond, is your go-to for leveling up your retention game. Jimmy, Founder and mastermind behind Sendlane, brings over 15 years of hands-on experience in building successful SaaS companies, along with valuable experience growing a DTC brand. Chase, Partner at Structured, has driven over $200 million in email-attributable revenue and is named the #1 influencer to follow in eCommerce. Together, this power duo breaks down the art and science of retention marketing into bite-sized, actionable tactics.

  1. hace 2 días

    10 retention plays you can't afford to miss

    (Free download) Steal our notes from the Retention Roadshow: https://ecomemailmarketer.com/notes-from-retention-roadshow We 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 free Want to get in on the action? Replay all the Roadshow sessions here: The 2026 Email Flow Playbook: https://www.youtube.com/watch?v=7I4BDLim4t8 Retention Marketing Playbook: https://www.youtube.com/watch?v=tMbTAGO-IJc Email Marketing Myths Busted: https://www.youtube.com/watch?v=0z6jtSpwiyY Connected AI for Email & Retention Marketing: https://www.youtube.com/watch?v=AoPbAJllCrM 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=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 show 06:11 How many marketers are actually using AI, city by city 10:22 MCPs and connected AI, and why nobody knows them yet 12:29 Max's welcome flow and pop-up playbook 14:20 Philippe on early BFCM prep and the 80/20 rule 16:12 Rytis on real MCP use cases, including deliverability 19:05 The language and data that moves revenue 21:30 Anwar on the metrics that forecast brand health 22:46 Melanie's golden goose framework 25:19 Coach Danny on building projections with AI 26:34 Chris Lang on storytelling to grow a list 31:12 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    32 min
  2. 30 jun

    We pulled the data on every retention metric brands track, here are the 10 broken ones

    Is your dashboard lying to you? Download our free vanity metrics cheat sheet: https://ecomemailmarketer.com/sendit-vanitymetrics The 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 ones Here'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=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 show 01:25 Why your retention metrics are quietly lying to you 03:22 Hot take 1: Open rates are fundamentally broken 06:30 Hot take 2: Click rates are inflated by bots too 10:28 Hot take 3: ESP attribution is mostly a fantasy 14:23 Hot take 4: Revenue per recipient hides more than it reveals 17:35 Hot take 5: List size is a vanity metric 20:46 Hot take 6: AOV is the wrong way to measure most campaigns 24:17 Hot take 7: Industry benchmarks are mostly garbage 27:46 Hot take 8: Your LTV math is wrong 32:09 Hot take 9: Unsubscribe rate isn't measuring what you think 34:48 Hot take 10: The metrics leadership doesn't know to ask for 38:27 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    40 min
  3. 23 jun

    After auditing hundreds of brands, here are the 10 SMS mistakes we keep seeing

    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 seeing Here'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 overlook 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=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 show 03:07 Quick compliance disclaimer before we get into it 03:35 Hot take 1: Stop requiring a discount to get an SMS opt-in 07:04 Hot take 2: MMS beats SMS for revenue almost every time 09:44 Hot take 3: You should send way less SMS than you think 12:28 Hot take 4: Two-way SMS is overrated for most brands 16:34 Hot take 5: Transactional SMS is the most underrated surface in ecom 19:12 Hot take 6: SMS segmentation shouldn't look like email segmentation 22:21 Hot take 7: Keywords are wildly underused on SMS 26:18 Hot take 8: Most SMS compliance is theater 29:58 Hot take 9: Don't launch SMS until email is dialed in 33:49 Hot take 10: Stop using SMS for things email does better 36:08 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    38 min
  4. 16 jun

    We read every email marketing best practice and ranked the 10 worst ones

    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 ones Here'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 invisible Thank 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=Sendit Lone 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=podcast 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 show 03:12 Hot take 1: Aggressive welcome series win 06:06 Hot take 2: Subject lines aren't built for opens, they qualify 09:51 Hot take 3: Higher unsubscribes can mean higher revenue 14:28 Hot take 4: You're probably over-segmenting 18:07 Hot take 5: Your abandoned cart flow is too long 20:38 Hot take 6: A/B testing yourself into mediocrity 24:21 Hot take 7: Send more often, segment smarter 26:56 Hot take 8: Black Friday is overrated in its current form 30:11 Hot take 9: Email design matters less than you think 34:31 Hot take 10: Stop copying your competitors 37:53 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    39 min
  5. 9 jun

    The death of retention teams how to operate as a 1 person army in 2026

    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 retention 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=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/ ______ 01:11 Podcast Intro and Hot Take 02:25 Beauty Brand Case Study 05:00 Why Teams Are Restructuring 05:25 Force One Margin Pressure 08:41 Force Two AI Quality Leap 11:30 Force Three Tooling Maturity 15:08 One Person Retention Role 17:00 Four Core Jobs in 2026 20:24 Directing AI With Prompts 22:52 Quality Control and Brand Voice 26:05 AI Powered Performance Analysis 28:17 Compensation and Job Security 30:48 Brand Loaded AI Projects 34:33 Production Tools And Design 36:53 Analytics Feedback Loop 40:03 One Person Team Risks 41:17 Documentation And Backup Plans 43:08 Quality Drift And QA45:04 Tunnel Vision And Pushback 48:11 Creative Sameness Problem 50:25 Burnout And Community 52:00 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    59 min
  6. 2 jun

    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 workflow Thank 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=Sendit Lone 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=podcast 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/ ______ 02:37 AI as Tool Not Toy 05:00 Three Practical Uses 07:57 AI Hype to Ignore 12:16 Real Time Savings 16:09 Where Not to Trust 20:26 Data Ceiling and MCP Intro 23:01 Bernard Explains MCP 28:41 MCP Setup and First Prompts 30:40 Connect Omnisend in Claude 32:06 Weekly Snapshot Prompt Demo 36:08 Metrics That Matter Most 38:50 Upsell Segments From Buyer Data 41:12 When AI Gets Too Generic 43:37 Repeat Winning Campaign Patterns 47:48 Customer Data Access Guardrails 51:36 Human in the Loop Framework 54:30 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    59 min
  7. 26 may

    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 converts Here'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 rates Thank 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=Sendit Lone 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=podcast 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/ ______ 02:57 Why SMS Is Different 03:25 Space And AI Compression 04:43 Context And Attention 05:39 Intimacy And Tone 06:43 Cost Frequency Segmentation 08:02 Hook Value Action Framework 10:48 Putting The Formula Together 13:27 Abandoned Cart Playbook 15:03 Replenishment Timing Texts 16:27 VIP Early Access Drops 17:06 VIP Drop Specifics 17:56 Flash Sale Formula 18:33 Mystery Discount Tests 19:59 AI Prompts For SMS 22:47 Prompt For Shortening 24:02 AI Variations For Testing 25:34 Replenishment Reminder Prompt 27:21 Testing Framework Basics 30:18 Common SMS Mistakes 31:40 Advanced SMS Tips 33:09 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    35 min
  8. 19 may

    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 output Here'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 them Thank 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=Sendit We'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 It 01:38 Prompts Matter Most 03:02 Four Prompt Layers 03:40 Layer One Context 04:57 Layer Two Task 05:37 Layer Three Constraints 08:21 Layer Four Format 09:29 Subject Line Prompts 11:36 Train With Past Wins 13:35 Curiosity Gap Testing 14:48 Campaign Idea Prompts 17:07 Pain Point Angles 18:51 Pain Point Prioritization 19:22 Seasonal Campaign Planner 20:16 Remix Past Winners 20:51 Email Body Copy Framework 23:01 AI As Copy Editor 24:28 Teach Brand Voice 25:43 SMS And Preview Text 28:26 Advanced Tips And Mistakes 30:31 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/yojimmykim https://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/@chasehunterdimond Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

    35 min

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The SendIt Podcast, hosted by email marketing experts and veterans Jimmy Kim and Chase Dimond, is your go-to for leveling up your retention game. Jimmy, Founder and mastermind behind Sendlane, brings over 15 years of hands-on experience in building successful SaaS companies, along with valuable experience growing a DTC brand. Chase, Partner at Structured, has driven over $200 million in email-attributable revenue and is named the #1 influencer to follow in eCommerce. Together, this power duo breaks down the art and science of retention marketing into bite-sized, actionable tactics.

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