Skip to content
Log in Join free
Send It! cover art

Send It!

Send It!

A Marketing and Business podcast

#52 in Marketing · 🇩🇰
Good podcast? Give it some love!

About the show

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.

Newest episodes

Don't Panic About BFCM 2026: Do These 10 Things Instead

24 min

You’re in the final stretch before Black Friday, and brands are either calmly executing or quietly panicking. On this episode of Send it! Podcast, Jimmy Kim and Chase Dimond skip the new ideas and give you the 10 things that actually move the needle right now, plus a few panic mistakes to talk yourself out of. The theme: discipline over panic. A calm brand executing a decent plan beats a frantic brand chasing a perfect one. What we cover: → Why you need to lock in your offer today (everything else depends on it) → Your final list cleanup and send volume warmup → How to launch an early access list, even this late → Why a real test order, including on mobile, saves your weekend → The flow conflict that quietly undercuts your sale (your homepage says 20% off, your welcome email says 10%) → How to map every send from the start of the sale through Cyber Monday → Why you should write your last chance and extension emails now → How to set a discount floor so you don’t panic-discount during a slow first hour → The two segments to build this week: VIP early access and recent buyer suppression → Your day after plan, and why BFCM is really an acquisition event If you only do one thing today: lock in your offer. Nothing else on the list can move until you do. Want the full prep list? Watch our 50 BFCM tips episode: [link] Download the free 50 BFCM Tips checklist: [link] CHAPTERS 00:00 Intro 02:21 Lock In Your Offer 03:57 List Cleanup and Warmup 06:08 Sponsor: Omnisend 06:57 Early Access Waitlist 08:29 Test Orders and Mobile QA 10:05 Audit Flows for Conflicts 11:34 Sponsor: Retention.com 12:58 Map Your Send Cadence 14:29 Write Deadline Emails Now 16:00 Set a Discount Floor 17:47 Build VIP and Suppression Segments 18:46 Sponsor: Allan 20:39 Day After Plan and Retention 22:46 Rapid Recap and Wrap THANK YOU TO OUR SPONSORS Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through perso...

Why Your eCom Subscribers Keep Canceling And How to Stop It - Part 2

27 min

You can be great at getting people into a subscription, but if they churn after a few cycles, all you’ve built is a leaky bucket. Jimmy Kim and Chase Dimond break down how to plug the leaks in Part 2 of our subscription and replenishment series. If you missed Part 1 (how to get customers in), watch it here: https://youtu.be/AXgvrdeBpSk What we cover: → Voluntary vs. involuntary churn, and why a big slice of your churn isn’t a decision at all → Dunning: pre-dunning, smart retries, card account updaters, and the “update your card” message → The real reasons subscribers cancel, and a fix for each one → Save offers that work: pause, skip, swap, adjust frequency, and downgrade → Why making cancellation a maze burns your brand → How to prevent churn before anyone reaches the cancel button → Why churned subscribers are one of your warmest win-back targets → The metrics that matter: voluntary vs. involuntary churn, churn by cycle, and failed payment recovery rate If you only do one thing this week: check your failed payment recovery, or find out whether you have a dunning setup at all. [object Object]Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/ Want to learn more about all things email and sms marketing? Chase and I have a master course: eCom Email Certified is...

Subscription vs. Replenishment: How to Get Customers Into Recurring Revenue (Part 1)

22 min

Most brands bolt a “Subscribe & Save” widget onto a product page, watch nobody use it, and decide subscription doesn’t work for them. Jimmy Kim and Chase Dimond argue the real problem is that they never understood what they were building. This is Part 1 of a two-part series on recurring revenue for consumable brands. Today is about getting customers in. Next week is about keeping them. What we cover: → The difference between subscription and replenishment (and why most consumable brands need both) → When subscription actually fits your product, and when forcing it makes churn worse → Why offering a subscription at first purchase churns faster, and when to offer it instead → Why you shouldn’t sell subscription on the discount alone → Non-price levers that make a subscription attractive: free shipping, bonuses, early access, flexibility → How to build a replenishment reminder around your product’s natural consumption cycle → Why one-tap reordering matters more than clever copy → How to use replenishment as the on-ramp that feeds your subscription program If you only do one thing this week: find the percentage of your repeat buyers on subscription vs. reordering manually, and your product’s natural reorder cycle. ______ Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getalla...

Similar podcasts

All episodes

Don't Panic About BFCM 2026: Do These 10 Things Instead

24 min

You’re in the final stretch before Black Friday, and brands are either calmly executing or quietly panicking. On this episode of Send it! Podcast, Jimmy Kim and Chase Dimond skip the new ideas and give you the 10 things that actually move the needle right now, plus a few panic mistakes to talk yourself out of. The theme: discipline over panic. A calm brand executing a decent plan beats a frantic brand chasing a perfect one. What we cover: → Why you need to lock in your offer today (everything else depends on it) → Your final list cleanup and send volume warmup → How to launch an early access list, even this late → Why a real test order, including on mobile, saves your weekend → The flow conflict that quietly undercuts your sale (your homepage says 20% off, your welcome email says 10%) → How to map every send from the start of the sale through Cyber Monday → Why you should write your last chance and extension emails now → How to set a discount floor so you don’t panic-discount during a slow first hour → The two segments to build this week: VIP early access and recent buyer suppression → Your day after plan, and why BFCM is really an acquisition event If you only do one thing today: lock in your offer. Nothing else on the list can move until you do. Want the full prep list? Watch our 50 BFCM tips episode: [link] Download the free 50 BFCM Tips checklist: [link] CHAPTERS 00:00 Intro 02:21 Lock In Your Offer 03:57 List Cleanup and Warmup 06:08 Sponsor: Omnisend 06:57 Early Access Waitlist 08:29 Test Orders and Mobile QA 10:05 Audit Flows for Conflicts 11:34 Sponsor: Retention.com 12:58 Map Your Send Cadence 14:29 Write Deadline Emails Now 16:00 Set a Discount Floor 17:47 Build VIP and Suppression Segments 18:46 Sponsor: Allan 20:39 Day After Plan and Retention 22:46 Rapid Recap and Wrap THANK YOU TO OUR SPONSORS Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through perso...

Why Your eCom Subscribers Keep Canceling And How to Stop It - Part 2

27 min

You can be great at getting people into a subscription, but if they churn after a few cycles, all you’ve built is a leaky bucket. Jimmy Kim and Chase Dimond break down how to plug the leaks in Part 2 of our subscription and replenishment series. If you missed Part 1 (how to get customers in), watch it here: https://youtu.be/AXgvrdeBpSk What we cover: → Voluntary vs. involuntary churn, and why a big slice of your churn isn’t a decision at all → Dunning: pre-dunning, smart retries, card account updaters, and the “update your card” message → The real reasons subscribers cancel, and a fix for each one → Save offers that work: pause, skip, swap, adjust frequency, and downgrade → Why making cancellation a maze burns your brand → How to prevent churn before anyone reaches the cancel button → Why churned subscribers are one of your warmest win-back targets → The metrics that matter: voluntary vs. involuntary churn, churn by cycle, and failed payment recovery rate If you only do one thing this week: check your failed payment recovery, or find out whether you have a dunning setup at all. [object Object]Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/ Want to learn more about all things email and sms marketing? Chase and I have a master course: eCom Email Certified is...

Subscription vs. Replenishment: How to Get Customers Into Recurring Revenue (Part 1)

22 min

Most brands bolt a “Subscribe & Save” widget onto a product page, watch nobody use it, and decide subscription doesn’t work for them. Jimmy Kim and Chase Dimond argue the real problem is that they never understood what they were building. This is Part 1 of a two-part series on recurring revenue for consumable brands. Today is about getting customers in. Next week is about keeping them. What we cover: → The difference between subscription and replenishment (and why most consumable brands need both) → When subscription actually fits your product, and when forcing it makes churn worse → Why offering a subscription at first purchase churns faster, and when to offer it instead → Why you shouldn’t sell subscription on the discount alone → Non-price levers that make a subscription attractive: free shipping, bonuses, early access, flexibility → How to build a replenishment reminder around your product’s natural consumption cycle → Why one-tap reordering matters more than clever copy → How to use replenishment as the on-ramp that feeds your subscription program If you only do one thing this week: find the percentage of your repeat buyers on subscription vs. reordering manually, and your product’s natural reorder cycle. ______ Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getalla...

Your 50 Black Friday Cyber Monday eCommerce Checklist for Email & SMS

26 min

Black Friday Cyber Monday is the biggest revenue weekend of the year for most brands, and most of the work is done weeks before it starts. Jimmy Kim and Chase Dimond fire off 50 quick hits to get your email and SMS program ready, grouped into 5 batches of 10. Their core frame: BFCM is a funnel clearing event. All year you’ve been filling the funnel. This is the weekend every fence sitter finally converts. What we cover: → Mindset and strategy (why more sends isn’t a strategy, and what the weekend is really for) → Planning and prep (build your calendar backwards, warm up your list in October, clean your list before the surge) → Offers, creative and copy (why non-discount levers still work and how to protect your margin) → Flows, segmentation and SMS (the evergreen flow conflict that quietly eats your weekend) → Execution and what happens after (live deliverability monitoring, rollback plans, and why you can’t go dark for Q5) One tip from the episode: don’t try to fix all 50. Pick the three you know you’re getting wrong and fix one today. Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/ Want to learn more about all things email and sms marketing? Chase and I have a master course: eCom Email Certified is a hands-on, results-driven program with a step-by-step...

Does Anyone Care About Halloween? (Your Q4 On-Ramp Playbook)

26 min

Most brands treat Halloween like a one-off email they throw together on October 30th. On this week’s episode of Send it! - Jimmy Kim and Chase Dimond argue that’s the wrong way to think about it. If you don’t sell costumes, Halloween isn’t really about Halloween. It’s your on-ramp into Q4. They break down whether Halloween is worth your time, how to time it based on what you sell, and how to run it so it warms up your list for BFCM instead of cannibalizing it. What we cover: → Whether your customers actually care about Halloween (and which brands it’s a real revenue event for) → Why Halloween is the bridge between Labor Day and Black Friday → The timing framework: hard-deadline brands vs. everyone else → Why you should never send your big push on Halloween night → How to extend your run past October 31st without going dark → How to avoid pulling sales forward from BFCM by accident → A tactical playbook: creative, offers that aren’t discounts, segmentation, and email + SMS timing → How to measure whether Halloween was incremental or just borrowed revenue If you’re only answering one question this week, make it this: is Halloween a real revenue event for your brand, or a warm-up into Q4? Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/ Want to learn more abou...

Stop ignoring these emails (they get the most opens)

27 min

Download the transactional playbook here: https://ecomemailmarketer.com/send-it/transactional-playbookEmail and SMS marketers obsess over your campaign subject lines, A/B test your hero images, and argue about send times. Meanwhile the emails with the highest open rates in your entire business are sitting untouched: your order confirmation, your shipping notification, your “out for delivery” email. On today’s epsisode of Send it! Podcast, Jimmy Kim and Chase Dimond break down why transactional emails get opened at 80-100%, why almost every brand treats them like pure plumbing, and exactly how far you can push them before you cross a real legal and deliverability line. What we cover: → Why transactional emails get opened at rates your campaigns can only dream of → The psychology behind every stage of the shipping journey (order confirmation, shipping, out for delivery) → The two dumb reasons brands never touch these emails → The legal concept of “primary purpose” and why it protects transactional sends → The deliverability risk of jamming promotional content into a transactional stream → A full email-by-email playbook: what belongs in your order confirmation, shipping notification, out-for-delivery email, post-delivery follow-up, and back-in-stock alert → How to measure whether your additions are actually working, without compromising the core message If you’ve never opened your own order confirmation email as a customer, this episode will change how you think about it. *** Thank you our friends at Omnisend, Retention and Allan for the sponsorship! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_...

100 things we learned about email and sms marketing in ecommerce

36 min

Download the 100 here: https://ecomemailmarketer.com/sendit-100 This week, we’re celebrating episode #100 with a fun 100 things we know about retention. Here’s what we cover in the pod: → Lists and list growth (why size is a vanity metric, and what actually matters instead) → Deliverability (the habits that quietly protect or destroy your sender reputation) → Segmentation (why over-segmenting is procrastination in disguise) → Flows (the automations every brand should have and rarely maintains) → SMS (the rules that are different from email, and why) → Copy and creative (what actually gets opens, clicks, and conversions) → Offers and discounts (why discounting is a tool, not a strategy) → Strategy and LTV (why retention funds acquisition, not the other way around) → Metrics (which numbers actually matter, and which ones are just noise) → Mindset (the operator habits that separate good retention marketers from great ones) Whether you’re brand new to retention marketing or you’ve been doing this for years, there’s something in this list that’s going to challenge how you’re currently running your program. We’re also giving away a free downloadable checklist of all 100 things:. ***** Thank you our SPONSORS of the show who allow us to share valuable and free information to you every week: Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com...

How to do winback campaigns in ecommerce

27 min

Win-Backs Are Broken Because Everyone Treats Them Like One Thing Most brands treat “win-back” like it’s one flow. On this week’s show, Jimmy Kim and Chase Dimond argue that’s the exact reason win-backs underperform almost everywhere, because a win-back is actually two completely different problems wearing the same name. They break down the two buckets every brand needs to separate: the lapsed customer (someone who already bought and proved their intent) and the lapsed prospect (someone who joined your list but never converted). Treating them the same doesn’t just waste a message, it actively hurts both. What we cover: → Why a lapsed customer deserves patience, not a panic discount → The ladder approach to winning back customers without training them to wait for a sale → Why a lapsed prospect’s intent has a shelf life, and why speed matters more than anything → Why being aggressive with a cold prospect is the right move, not a risky one → Why unengaged prospects need to be sunset, and how holding onto them hurts your deliverability for everyone else → How to measure the two buckets differently instead of judging them by the same metric If your win-back flow is just a single “we miss you” email going out to everyone who’s gone quiet, this episode explains exactly why it’s not working the way you think it is. Thank you our SPONSORS of the show who allow us to share valuable and free information to you every week: Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on...

The only KPI a retention marketer should be thinking about..

29 min

This is the the most Important number in Retention Marketing nobody tracks Every brand celebrates new customer count. On this week’s episode, Jimmy Kim and Chase Dimond argue that’s the wrong number to be proud of, and that the real moment that determines a customer’s lifetime value is the second purchase, not the first. They break down why a first-time buyer isn’t really a customer yet, just someone willing to give you a chance, and why the shift from trial to identity is the actual psychological threshold every retention program should be built around. What we cover: → Why repeat purchase probability compounds after the second order, and what that means for your acquisition budget → The psychological difference between a first purchase (trial) and a second purchase (identity) → Why discounting the second purchase trains the exact behavior you don’t want → How to find your product’s natural reorder window instead of guessing → 5 concrete playbooks for the post-purchase window: post-purchase sequence, replenishment nudge, cross-sell, bounce-back offer, and subscription conversion → The two numbers almost no brand tracks: cohort-based repeat purchase rate and median time to second order If you’ve ever wondered why your acquisition numbers look great but revenue feels flat, this episode explains where the leak actually is. Subscribe for new episodes every week. Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Create Emails like Ads: getallan.com eCom Email Certified is a hands-on, results-...

We Asked Retention.com's Founder If This Is Legal (ft. Adam Robinson)

32 min

The Legal Loophole Behind Non-Opt-In Email Marketing Is it actually legal to email people who never opted in? This week, Jimmy Kim sits down with Adam Robinson, founder of Retention.com and RB2B, to break down how identity resolution and non-opt-in email marketing actually work, and why it’s compliant under U.S. law even though most people assume it isn’t. Adam built Retention.com (formerly GetEmails) into the market leader in this space, and in this episode he explains exactly how the legality works, how deliverability actually gets protected, and what separates a smart list growth strategy from one that gets a brand blacklisted. What we cover: → Why non-opt-in email marketing is legal under CAN-SPAM, and why so many people think it isn’t → The 1-2% rule that keeps deliverability safe when adding non-opt-in contacts → Who this strategy actually works for (hint: it’s not a brand new store) → The difference between Retention.com’s two products: aggressive list growth vs. conservative cart recovery → Why the biggest Shopify brands use multiple identity vendors at once, not just one → How Adam priced RB2B at $79/month instead of a $12,000 sales-led deal, and why → Why events and in-person relationships still drive most vendor decisions in ecommerce If you’ve been skeptical about identity resolution tools or unsure whether they’re worth the risk, this episode answers the questions most people are too embarrassed to ask. Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learn...

10 Email Copywriting Rules You Should Break in 2026

41 min

Everyone's copywriting "rules" are recycled from 1960s direct mail and copywriting Twitter . In this episode, Jimmy Kim and Chase Dimond go through 10 sacre copywriting rules and explain why most of them no longer hold up in 2026 inboxes and beyond.From why long-form email is quietly outperforming short copy, to why the "one CTA per email" rule is only half right, to why first name personalization barely moves the needle anymore, this episode breaks down what actually converts vs. what copywriters keep repeating because everyone else does.What they cover:- Why long-form email copy is winning (and how AI changed the math)- The real rule behind CTAs: one goal, not one button- Why personalization tokens are overrated and segment-level relevance wins- Statement hooks vs. question hooks- Why most brand storytelling in email is wasted space- The most under-optimized line in your email (hint: it's not the subject line)- Why the PS line still converts and nobody uses it- Why trying to be funny in email usually backfires- Why fake urgency has trained your customers to ignore you- Writing email copy like you're texting a friend, not presenting to a boardThank you our friends at Omnisend and Retention.com for sponsoring the podcast!Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastLet's hang out IRL! Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.come...

Your retention stack is missing this channel

40 min

No matter how good your abandoned cart emails are, most of that lost revenue never comes back. What if an AI could just call and ask why? In this episode of Send It, Jimmy and Chase talk with Will Nauseda, founder of Outcraft about the retention channel almost no one is using: voice. Outcraft built an AI that calls abandoned-checkout shoppers and has real conversations, answering the questions email and SMS can't. They get into why AI voice finally sounds human, why a call often recovers the sale without a discount, where it fits in your flow, what it actually costs, and why the early-mover advantage looks a lot like SMS three years ago. Find Will and Outcraft: Outcraft: https://www.outcraft.ai/?utm_source=Podcast&utm_medium=SendIt Will Nauseda: https://www.linkedin.com/in/will-vilius-nauseda-a10278b1/ Here's what they get into: - Why voice is the overlooked fifth retention channel - How AI voice got good enough to feel human, while staying disclosed - Why a call often recovers the sale without a discount - Where voice fits in your abandoned-checkout flow, and the quiet-hours rules - What it actually costs, priced per profile instead of per call Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.com...

The "other" BFCM ecom marketers forgot about

26 min

(Free download) Ready Made Demand: The Retention Marketer's Guide to Cashing in on The Calendar - https://ecomemailmarketer.com/ready-made-demand Right now your customers are rebuilding their whole routine, and almost no brand is marketing to it. In this episode of Send It, Jimmy and Chase break down how to own a seasonal moment even if you've never sold a school supply in your life. Using back to school as the case study, a $147 billion season and the second biggest of the year, they lay out what actually makes a "moment," the framework for attaching your brand to one without it feeling forced, and the five plays that turn it into revenue. EP 94: The $147B season you're ignoring Here's what they get into: - Why back to school is a mindset, not a date, and the second New Year for your list - The three things that make a moment worth stealing - The stretch test for attaching your brand without it feeling forced - The five plays: bundles, routine stories, segmentation, urgency, and offers - The timing calendar, and why the moment already started back in July Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.com UpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,00...

How a 12-person team outputs like 100 people

38 min

Patrick's team is just 12 people, but it outputs like a team of 100. That gap is the whole story of where marketing is going. In this episode of Send It, Jimmy talks with Patrick Haede, co-founder and CEO of Superscale AI, about how AI is changing what a marketer actually does. Having studied thousands of ad creatives, his case is simple: once building a product gets this easy, distribution becomes the moat and creative is the lever inside it. They get into why only about 5% of ads ever win, why the human moves up the stack to brand, judgment, and taste, and the meme with no logo that became a brand's best ad, plus why Patrick runs a 12-person company with the output of 100 agents. Here's what they get into: - The creative machine that beats guessing which ad will win - Why only about 5% of ads are ever real winners - How the marketer's job shifts from doing the work to orchestrating AI agents - The meme with no logo that became a brand's best-performing ad - What separates a 10x marketer from everyone else now Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.com eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious...

We're calling Black Friday 2026 right now

37 min

(Free download) Access our Black Friday & Cyber Monday cheat sheet: https://ecomemailmarketer.com/send-it/bfcm-2026 The real question isn't what Black Friday makes you. It's what it costs you afterward. In this episode of Send It, Jimmy and Chase run 10 hot takes on Black Friday and Cyber Monday, and why most of the advice retention marketers have followed for five years is now outdated or actively working against them. They get into how extended sale windows killed urgency, how the send-more playbook torches your deliverability into January, and what to actually do differently before the season hits. EP 92: We're calling Black Friday 2026 right now Here's what they get into: - Tighter sale windows, Thanksgiving sends, and the Cyber Monday profit brands overlook - Offer creativity that beats racing everyone to the deepest discount - Sending fewer, smarter emails and texts so BFCM doesn't torch your deliverability - The worst-LTV customers BFCM brings in, and running it as a retention play instead - Beating the self-inflicted post-BFCM slump and spreading revenue across the whole year Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.com eCom Email Certified is a hands-on, results-driven program with...

Unlock true 1:1 email personalization w/ Allan

43 min

(Free download) Unlock true 1:1 personalization: https://ecomemailmarketer.com/send-it/personalization-ladder Personalization has been email's holy grail for a decade, yet we're still sending everyone the same email. In this episode of Send It, Jimmy Kim sits down with Liam Veregin and Jacob Paduch, co-founders of the agency Aplo and the AI personalization tool Allan, to get into what email personalization actually means in 2026. They break down why it's stayed a buzzword for a decade, why the wave of AI email builders solves a labor problem instead of the real one, and how borrowing Meta's creative-serving model changes what a retention program can do. Real personalization was never a first name in the subject line, it's the content, the offer, and the timing actually changing for each person. Check out allan: Website: https://getallan.com X: https://x.com/getallanai LinkedIn: https://www.linkedin.com/company/getallan/ EP 91: Unlock true 1:1 email personalization Here's what they get into: - How Meta serves creative, and why email never worked that way - Sending a genuinely unique email to every subscriber on your list - Why one-to-one content lifts revenue per recipient - Bolting personalization onto your ESP with no migration or IP warming - Where personalization goes next: on -site, CRO, and data enrichment Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ 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 02:28 Meet Liam and Jacob from Allan...

He ranked 3,000 quizzes

44 min

Access Jonathan’s FREE eCommerce Quiz Audit Button: https://optimizeyourquiz.com/research/best-and-worst Every question your quiz asks costs the buyer something. And the best ones make it worth paying. In this episode of Send It, Jimmy Kim and Chase Dimond sit down with Jonathan Drake, who audited and ranked more than 3,000 ecommerce quizzes across 27 benchmark points to find out what separates the best quiz funnels from the worst. They dig into why the first question matters so much, how brands lose shoppers at the email and SMS capture step, when 6-9 questions can actually work, and why quizzes should feel more like guided product discovery than a default template built to collect zero-party data. Jonathan also shares what he learned from ranking the top and bottom ecommerce quizzes, including how visitor experience, business leverage, readability, product discovery, and lead capture all play into whether a quiz helps shoppers buy or just creates more data your team never uses. Follow Jonathan on social: https://x.com/JonathanDrake https://www.linkedin.com/in/jonathanrdrake/ Here's what we're diving into: - The survey vs quiz difference most brands get wrong - Where quizzes lose people, and how to earn the email - Why more questions can actually mean a better customer - Using a quiz as a product discovery and selling tool - Where AI and the "conversation" model fit in Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast Want to spend two days learning alongside some of the smartest operato...

10 AI mistakes wrecking your retention

48 min

Download our 4-part briefsheet for better AI prompts >> www.ecomemailmarketer.com/ai-prompt-brief AI won’t fix a weak retention program. It’ll just help you break it faster. In this episode of the Send It Podcast, Jimmy Kim and Chase Dimond get into the real AI conversation email and SMS marketers should be having: where AI actually helps, where it quietly hurts, and why the tool itself isn’t the advantage anymore. From generic subject lines and fake-looking imagery to black-box segmentation and overhyped ESP features, this episode breaks down how ecommerce brands can use AI without losing the trust, voice, and strategic judgment that make retention marketing work. EP 89: 10 AI mistakes wrecking your retention Here's what we're diving into: - Why AI-generated subject lines are making every brand sound the same - How fake-looking AI imagery can erode customer trust - Why “AI-powered” ESP features still need to prove their lift - How to build AI workflows with prompts, brand context, and QA checks - Why the future belongs to strategic, AI-native retention marketers Thank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/ 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 03:35 Hot take 1: AI subject lines make every brand sound the same 06:38 Hot take 2: AI imagery is quietly costing you trust 12:20 Hot take 3: If you're not using AI, you'll fall behind 16:16 Hot take 4: AI segmentation is a dangerous black box 20:13 Hot take 5: AI copy needs way more editi...

10 retention plays you can't afford to miss

32 min

(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...

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

40 min

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...

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

37 min

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 a...

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

38 min

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 hour...

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

58 min

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, result...

EP 83: How to Use MCP with your ESP (Step by step tutorial w/ prompts)

58 min

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. Truste...

EP 82: The 160-character masterclass: Writing SMS that actually converts

35 min

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 Roadsho...

EP 81: AI prompt engineering for email marketers: The templates that actually work

34 min

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-dri...

EP 80: The 7 AI prompts every email marketer needs

22 min

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-prompt Here'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 claims 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 c...

EP 79: Why most welcome series fail (and the 4 email framework that works)

32 min

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 performance 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, r...

EP 78: The unsubscribe paradox every marketer gets wrong

27 min

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 wrong Here'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 panic 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 show 02:23 The unsubscribe para...

EP 77: Agency vs in house: When to hire, when to fire

29 min

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 fire Here'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 yourself 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 show 02:15 What agencies are actually good at (and where they fall short) 06:03 The case for hiring an agency 08:43 Using an agency for one-off projects 10:30 What you should never ou...

EP 76: How to produce 5x more email and SMS content with AI

37 min

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 AI Here'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 insight 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...

EP 75: How to A/B test emails when the old playbook is broken

32 min

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 2026 Here'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 noise 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 show 01:13 Why email testing got so...

EP 74: Conversion psychology: 6 principles for retention marketers

32 min

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 marketers Here's what they cover: Why educational emails outperform promotional ones every time The urgency mistake that quietly trains your list to ignore you How to diagnose and remove the friction killing your conversions The subject line technique that makes people feel compelled to open Why the brands with the highest LTV sell identity, not just products How small actions like quizzes and reviews build toward a purchase A simple checklist to audit any email before you hit send A real replenishment email breakdown that hits five principles at once 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 show 02:30 Principle 1: Reciprocity - give value befor...

EP 73: Our 5 step ESP migration warmup guide

35 min

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 guide Here's what they cover: The three reasons most ESP migrations fail before they start Step 1: Setting up a fresh subdomain and authenticating SPF, DKIM, and DMARC Step 2: Configuring platform settings before sending a single email Step 3: Connecting your store and rebuilding your flows the right wayStep 4: The segmentation strategy that separates buyers from prospects and why it matters Step 5: Monitoring reputation by TLD and what to do when things go wrong When to hire help and what a managed migration actually costs 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 show 02:44 Why most ESP migrations fail before they even start 05:55 Step 1: Setting up your new subdomain the right way 09:26 Step 2: Configuring your platform...

EP 72: Why discounts are hurting your brand + what to do instead

35 min

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 instead Here’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 marketing 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://...

EP 71: The funniest things email marketers did in 2025

32 min

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 intentional 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...

EP 70: 6 Retention habits of 8 and 9 figure DTC brands

46 min

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 brands Here'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 learnin...

EP 69: How to embrace AI as an email marketer + 3 hot click tips

38 min

AI is everywhere in email marketing… but is it actually working In 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 tips Here'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 emerge 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...

EP 68: A practical framework for profitable email and SMS in 2026

45 min

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 2026 Here'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 framework 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: SE...

EP 67: The new definition of engagement (and the metrics that actually matter)

29 min

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 Show 02:21 Redefining Engagement Metrics...

EP 66: 12 Unusual segments that drive serious eCommerce revenue

43 min

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 revenue Here'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 positioning 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 Show 04:29 Why Microsegmentation Matters for Your Business 09:33 12 Unusual Segments for Revenue Growth 09:46 Disc...

EP 65: Why the first 45 days matter more than the first purchase

38 min

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 purchase Here'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 breakdowns 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 Show 03:02 The Critical First 45 Days of a Subscriber's Life 08:08 Breaking Down the First 45 Days into Stages 16:00 Creating Micro Moments and Micro Wins 20:27 Understanding Habit Loops: Cue, Routine, Reward 23:00 Building Habits Through Email and SMS 26:37 The Im...

EP 64: What we learned from 41 billion emails sent in 2025

43 min

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 2025 Here'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 prioritize 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 Show 02:17 Key Insights from the Report 07:54 Transact...

EP 63: The retention audit: How to diagnose any brand in 60 minutes

39 min

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 minutes Here'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 timing 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://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 Show 03:12 Retention Audit Framework Overview 04:17 Data Infrastructure: The Foundation 08:51 Deliverability and List Quality 15:37 Lifecycle Automation: Maximizing Revenue 20:17 The Importance of Timely Replenishment 23:09 E...

EP 62: The secret behind the click and why click tracking is so important

34 min

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 important Here'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 conversions 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://eemtrk.com/omnisend-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://eemtrk.com/eec-sendit Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox ______ 00:00 Welcome to The Show 02:08 Deep Dive into Clicks 05:04 Types of Clicks E...

EP 61: Here's what AI says about retention marketing in 2026

36 min

AI just predicted the future of retention marketing… but is it accurate? In this episode, Jimmy Kim and Chase Dimond ask ChatGPT to generate bold 2026 predictions for ecommerce email and SMS marketers and then break down what they agree with, what’s BS, and what might already be happening. From segmentation going predictive to retention teams owning margin and profit, this episode is packed with strategic insights and real-world examples from brands, agencies, and operators doing the work. EP 61: Here's what AI says about retention marketing in 2026 Here's what we're diving into: - Why your flows might be worth more than your campaigns - What retention marketers will actually be judged on in 2026 - Predictive segmentation, emotional copywriting, and deliverability as a job requirement - How SMS will get leaner and more profit-focused - The rise of behavioral targeting over traditional KPIs Thank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast! 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-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://eemtrk.com/eec-sendit Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox ______ 00:00 Welcome to the Show 04:26 Cohort Yield vs. Campaign Revenue 06:44 Flow Weight vs. Campaigns 10:32 Strategic Use of SMS 13:13 Importance of Deliverability 15:32 Predictive Segmentation 17:55 Creative Testing: Emotion vs. Design 18:13 Behavioral Copy Strategies for Marketers 20:40 T...

EP 60: Gmail’s new rules: What every email marketer needs to know

41 min

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 know Here'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 in Read more about the deliverability report: https://e.eemtrk.com/gmail-changes-sendit Thank 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-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://eemtrk.com/eec-sendit Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox ______ 00:00 Welcome to The Show 00:53 Overview of Gmail Changes 03:47 Gmail's Managed Subscription View 11...

EP 59: The real lessons from Black Friday + Cyber Monday 2025

39 min

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 2025 Here'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 results Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://eemtrk.com/omnisend-sendit Kintsugi 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-kintsugi eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://eemtrk.com/eec-sendit Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML,...

EP 58: Don’t go silent after BFCM (Here’s what to send next)

30 min

Most brands blow their budget on BFCM and then ghost their best customers. In this episode of Send It, Jimmy Kim and Chase Dimond break down what happens when you go silent after Black Friday and how to fix it. You’ll learn how to turn high-intent, one-time buyers into loyal, high-LTV customers using a proven 4-stage retention strategy. They share the campaigns to send, the exact follow-up timing, and 5 post-BFCM metrics to track to keep your Q4 profitable after the sale. EP 58: Don’t go silent after BFCM (Here’s what to send next) Here's what we're diving into: - Why second purchases are the key to post-BFCM profitability - The biggest mistake brands make after Black Friday - A 4-stage post-purchase flow: onboarding, education, bridge offer, nurture - 5 plug-and-play campaigns to send right now - The metrics that matter: time-to-second-purchase, flow conversion, and more Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://eemtrk.com/omnisend-sendit Kintsugi 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-kintsugi eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://eemtrk.com/eec-sendit Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox ______ 00:00 Welcome to The Show 03:56 The Importance of Recency, Intent, and Volume 07:37 Com...

EP 57: How often should you really email your list?

35 min

What's the perfect email cadence? Daily, weekly, or just when you have something to say? In this episode, Jimmy and Chase break down the pros and cons of different email frequencies (daily sends, weekly campaigns, and launch-only strategies) and help you figure out what cadence is right for your brand. They share real examples, revenue-impacting data, and a step-by-step framework to test and dial in your ideal email frequency; without burning your list or obsessing over unsubscribes. EP 57: How often should you really email your list? Here's what we're diving into: - Daily vs. weekly vs. campaign-based sending (and what actually works) - A real-world test: 2 emails/week vs. 5 emails/week (+70% revenue) - Why open rates and unsubscribes matter less than you think - 5 factors that determine the right cadence for your brand - How to segment your list by frequency without overwhelming subscribers - The “steady + burst” strategy top brands use to scale email without burnout Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast! Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://eemtrk.com/omnisend-sendit Kintsugi 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-kintsugi eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://eemtrk.com/eec-sendit ______ 00:00 Welcome to The Show 04:40 Pros and Cons of Daily Emails 07:00 Who Should Send Weekly (and Why) 08:35 Campaign-Only Sending: When It Works 10:20 Real-World Cadence Test: 2x vs 5x Per Week...

See all 106 episodes

–

0 ratings from members

5
4
3
2
1

Rate this podcast

Log in to rate and review the shows you listen to.

No reviews yet — be the first member to rate "Send It!".

This podcast, its content and its artwork are not owned by, affiliated with, or endorsed by Castquire.

Keep listening

Discover more podcasts like this.

Browse podcasts See the charts

Up next

  1. Nothing queued. Use + Queue on any episode to line it up.

0:00 0:00

Cookies

We set only what the site needs to sign you in and remember your theme. No advertising, no analytics. Read more.