Explorez tous les épisodes du podcast Send It!

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 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/

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#bfcm #blackfriday #cybermonday #emailmarketing #ecommerce #retentionmarketing #smsmarketing

Send It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing: email, SMS, and ecommerce growth. Subscribe for new episodes every week.

0:00 Intro

1:30 BFCM as a funnel clearing event

2:30 Batch 1: Mindset and strategy (tips 1-10)

5:30 Sponsor: Omnisend

7:30 Batch 2: Planning and prep (tips 11-20)

10:30 Batch 3: Offers, creative and copy (tips 21-30)

13:30 Sponsor: Retention.com

14:30 Batch 4: Flows, segmentation and SMS (tips 31-40)

18:00 Batch 5: Execution and after the weekend (tips 41-50)

21:00 Sponsor: Allan

22:30 Tips 49-50: debrief and what BFCM is really for

25:00 Wrap up: fix three, not fifty

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Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 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 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/

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00:00 Intro

01:39 Do Customers Care About Halloween?

03:19 Halloween as a Q4 On-Ramp

04:17 Who Is Halloween Worth It For?

06:27 Sponsor: Omnisend

08:46 The Timing Framework

11:05 Don’t Send Night Of

11:58 Extend Past Halloween

14:23 Sponsor: Retention.com

15:30 Avoid BFCM Cannibalization

18:39 Halloween Playbook Tactics

21:16 Sponsor: Allan

23:19 Measuring Success

24:43 Wrap Up and Takeaway

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Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

#halloweenmarketing #emailmarketing #ecommerce #retentionmarketing #BFCM #q4marketing

Download the transactional playbook here: https://ecomemailmarketer.com/send-it/transactional-playbook
Email 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_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 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/

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00:00 Intro

03:01 Why Transactional Wins

05:04 Ignored Inbox Goldmine

08:24 Switch to Omnisend today

09:43 Trojan Horse Reframe

11:11 Legal and Deliverability Lines

15:19 Identify visitors with Retention

16:59 Email by Email Playbook

21:38 Personalization that works with Allan

23:10 Tracking and Risk Monitoring

25:14 Action Steps

26:36 Final Wrap and Outro

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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/

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 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/

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00:00 Intro

00:54 Welcome to 100!

02:26 List Growth Truths

06:05 Deliverability Essentials

08:41 Segmentation That Works

11:11 Omnisend is Awesome

13:44 Flows Money Machine

16:28 SMS Principles Start

17:54 SMS Rules Recap

18:55 Retention.com is great

20:03 Coordinating Email and SMS

20:24 Copy and Creative Wins

22:09 Unsubscribes and Usefulness

22:43 Discounts Without Damage

26:21 LTV and Retention Strategy

28:49 Allan Personalization is a must try

29:56 Metrics That Matter

33:07 Operator Mindset Final 10

34:48 Wrap Up

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 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 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 Show Intro

01:22 Two Winback Buckets

04:22 Why Customer Lapse Hurts

06:16 Reframe Patience vs Speed

08:35 Customer Winback Ladder

11:21 Timing by Purchase Cadence

12:52 Prospect Window and Decay

15:41 Prospect Sprint Playbook

17:47 List Hygiene and Deliverability

21:43 Stop Hoarding Subscribers

23:18 Implementation and Metrics

25:23 Wrap Up Key Takeaways

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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-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/

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00:00 Intro

01:12 New Customers Aren’t Loyal

03:29 Why Second Purchase Matters

07:03 Trial to Identity Shift

08:49 Omnisend Migration Sponsor

10:57 Post Purchase Builds Trust

13:25 Timing by Category

16:19 Retention.com BFCM Sponsor

17:29 Email vs SMS Phases

19:16 Five Second Purchase Playbooks

24:03 Ecom Email Certified Plug

25:13 Measure Cohorts and Timing

28:10 Wrap Up and Homework

#retentionmarketing #ecommerce #emailmarketing #dtc #customerretention

Send It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing — email, SMS, and ecommerce growth.

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 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 results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

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00:00 Intro

00:47 Welcoming our guest

01:43 Is this legal? Breaking down CAN-SPAM

02:48 Compliance Explained

05:22 Deliverability Strategy: The 1-2% deliverability rule

07:43 Who Should Use It

10:40 Optimization Not Magic

12:05 Real World Use Case

14:00 Grow vs Reclaim

15:46 Competitors Copycats

17:50 Data Sources Providers

21:28 Events, community, and how this market actually buys

23:01 Pricing Shakeup: You lowered the price?

26:21 Final questions and outro

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Everyone's copywriting "rules" are recycled from 1960s direct mail and copywriting Twitter . In this episode, Jimmy Kim and Chase Dimond go through 10 sacre copywriting rules and explain why most of them no longer hold up in 2026 inboxes and beyond.From why long-form email is quietly outperforming short copy, to why the "one CTA per email" rule is only half right, to why first name personalization barely moves the needle anymore, this episode breaks down what actually converts vs. what copywriters keep repeating because everyone else does.What they cover:- Why long-form email copy is winning (and how AI changed the math)- The real rule behind CTAs: one goal, not one button- Why personalization tokens are overrated and segment-level relevance wins- Statement hooks vs. question hooks- Why most brand storytelling in email is wasted space- The most under-optimized line in your email (hint: it's not the subject line)- Why the PS line still converts and nobody uses it- Why trying to be funny in email usually backfires- Why fake urgency has trained your customers to ignore you- Writing email copy like you're texting a friend, not presenting to a boardThank you our friends at Omnisend and Retention.com for sponsoring the podcast!Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcastLet's hang out IRL! Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/______02:59 Hot Take 1: Long Copy06:46 Hot Take 2: Goal12:09 Hot Take 3: Personalization15:24 Hot Take 4: Question Hooks18:15 Hot Take 5: Storytelling21:20 Hot Take 6:The first line matters more than your headline25:02 Hot Take 7: PS Line Comeback28:21 Hot Take 8: Stop Trying Humor31:38 Hot Take 9: Urgency Overuse Trap36:29 Hot Take 10: Write Like You Text38:21 AI Makes It Corporate39:57 TLDR Wrap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/#emailmarketing #copywriting #ecommerce #retentionmarketing #klaviyoSend It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing: email, SMS, and ecommerce growth.Subscribe for new episodes every week.______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

No matter how good your abandoned cart emails are, most of that lost revenue never comes back. What if an AI could just call and ask why?

In this episode of Send It, Jimmy and Chase talk with Will Nauseda, founder of Outcraft about the retention channel almost no one is using: voice. Outcraft built an AI that calls abandoned-checkout shoppers and has real conversations, answering the questions email and SMS can't. They get into why AI voice finally sounds human, why a call often recovers the sale without a discount, where it fits in your flow, what it actually costs, and why the early-mover advantage looks a lot like SMS three years ago.

Find Will and Outcraft:

Outcraft: https://www.outcraft.ai/?utm_source=Podcast&utm_medium=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

UpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616

______

00:00 Welcome to the show

02:14 Meet Will Nauseda and the Outcraft story

07:17 The abandoned cart intent email misses

12:23 Breaking down a real AI voice call

18:33 Where voice fits in your flow

24:45 Why aggressive cart recovery wins

26:31 The risks and guardrails of voice

32:24 The low-risk way to test it

35:10 The omni-channel, conversation-first philosophy

38:33 Wrapping up and the future of voice

40:16 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

(Free download) Ready Made Demand: The Retention Marketer's Guide to Cashing in on The Calendar - https://ecomemailmarketer.com/ready-made-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 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616

______

00:00 Welcome to the show

03:14 Why this $147B moment matters right now

04:22 What actually makes something a moment

06:40 How any brand plays the routine reset

11:27 The three-question framework for any moment

12:58 The five plays that turn a moment into revenue

18:31 Why the moment beats a discount

19:32 The timing calendar, and why July already started it

23:58 The metrics that tell you it actually worked

24:47 Key takeaways and your low-risk first move

26:13 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Patrick's team is just 12 people, but it outputs like a team of 100. That gap is the whole story of where marketing is going.

In this episode of Send It, Jimmy talks with Patrick Haede, co-founder and CEO of Superscale AI, about how AI is changing what a marketer actually does. Having studied thousands of ad creatives, his case is simple: once building a product gets this easy, distribution becomes the moat and creative is the lever inside it.

They get into why only about 5% of ads ever win, why the human moves up the stack to brand, judgment, and taste, and the meme with no logo that became a brand's best ad, plus why Patrick runs a 12-person company with the output of 100 agents.

Here's what they get into:

- The creative machine that beats guessing which ad will win

- Why only about 5% of ads are ever real winners

- How the marketer's job shifts from doing the work to orchestrating AI agents

- The meme with no logo that became a brand's best-performing ad

- What separates a 10x marketer from everyone else 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 results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

01:59 Meet Patrick Haede and his founder journey

04:48 The ecommerce family business behind the lens

06:09 Why distribution is the new moat

12:06 What actually makes an ad win

16:49 The AI creative arms race is here

21:30 How marketers become orchestrators of AI agents

28:37 Inside Superscale AI

34:00 Why verticalized AI tools are winning

37:19 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

(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 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

02:59 Hot Take #1: Why Starting BFCM Earlier Is Hurting Sales

05:59 Hot Take #2: Bigger Discounts Don't Win Anymore

09:02 Hot Take #3: More Emails = More Damage During BFCM

13:46 Hot Take #4: BFCM Customers Are Your Lowest-LTV Cohort

16:49 Hot Take #5: Why Cyber Monday Can Be More Profitable Than Black Friday

19:30 Hot Take #6: Why You Should Be Sending on Thanksgiving

23:15 Hot Take #7: Your Q1 Slump Starts During BFCM

25:59 Hot Take #8: Most Brands Are Destroying Their SMS List

28:24 Hot Take #9: Stop Discounting Your VIP Customers

32:34 Hot Take #10: BFCM Shouldn't Make or Break Your Business

35:37 Key Takeaways & Wrap Up

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

(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

08:48 Why most personalization still falls flat

18:04 Can small lists personalize? The labor problem

23:24 Bringing paid ads logic to email

26:10 The testing leverage you can't do by hand

29:06 Covering more of your list without more work

34:35 Where allan goes next, beyond email

38:04 The Amazon-style experience DTC is chasing

41:47 Final thoughts and where to try allan

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 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 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

02:25 Meet Jonathan Drake: 18 years in email and data marketing

07:46 Why he audited 3,000 ecommerce quizzes

12:18 The survey vs quiz difference most brands miss

18:46 A tour of the quiz scoring dashboard

20:54 The push and pull between business and customer

23:25 How long a quiz should actually be

26:02 Breaking down a great candle quiz live

31:41 AI, conversations, and the Jack principles

36:26 The worst quizzes and the zero-party data trap

37:52 Quizzes vs pop-ups, and which protects your margin

43:04 Final thoughts and conclusion

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 editing than anyone admits

25:05 Hot take 6: Your AI workflow is the real moat

29:49 Hot take 7: ESPs are massively overselling their AI

34:48 Hot take 8: Human in the loop is worth more than you think

38:19 Hot take 9: AI is about to make everyone sound the same

43:27 Hot take 10: The retention marketer's job is changing fast

46:43 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

https://x.com/ecomchasedimond

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

(Free download) Steal our notes from the Retention Roadshow: https://ecomemailmarketer.com/notes-from-retention-roadshow

We just spent a week on the road talking retention marketing with ecommerce teams across New York, Miami, Los Angeles, and Austin.

And one thing became pretty clear: the conversations happening online don't always match what's actually happening inside ecommerce teams.

In this episode of Send It, Jimmy and Chase recap the Commerce Roundtable Retention Roadshow, sharing the biggest takeaways from four cities, seven days, and hundreds of conversations with retention marketers and ecommerce operators. They dig into where teams really stand with AI, the strategies that kept coming up in every room, and the tactical ideas worth bringing back to your own program.

If you want to keep a pulse on where retention marketing is actually headed, this episode is the place to start.

Here's what we're diving into:

- The real state of AI and MCP adoption across four cities

- Why 85% of first purchases happen on day zero, and the double send for it

- The 80/20 flow rule that's quietly wasting your time

- Using an MCP to crack open the deliverability black box

- Where to watch every full talk and grab the decks for free

Want to get in on the action? Replay all the Roadshow sessions here:

The 2026 Email Flow Playbook: https://www.youtube.com/watch?v=7I4BDLim4t8

Retention Marketing Playbook: https://www.youtube.com/watch?v=tMbTAGO-IJc

Email Marketing Myths Busted: https://www.youtube.com/watch?v=0z6jtSpwiyY

Connected AI for Email & Retention Marketing: https://www.youtube.com/watch?v=AoPbAJllCrM

Thank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

06:11 How many marketers are actually using AI, city by city

10:22 MCPs and connected AI, and why nobody knows them yet

12:29 Max's welcome flow and pop-up playbook

14:20 Philippe on early BFCM prep and the 80/20 rule

16:12 Rytis on real MCP use cases, including deliverability

19:05 The language and data that moves revenue

21:30 Anwar on the metrics that forecast brand health

22:46 Melanie's golden goose framework

25:19 Coach Danny on building projections with AI

26:34 Chris Lang on storytelling to grow a list

31:12 Final thoughts and where to watch every talk

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Is your dashboard lying to you? Download our free vanity metrics cheat sheet: https://ecomemailmarketer.com/sendit-vanitymetrics

The metrics every retention team reports up to the CFO might be quietly making the company worse.

Jimmy and Chase break down 10 hot takes on retention KPIs, why most of them are broken, and what to track instead. From inflated opens and bot-driven clicks to fake attribution, vanity list sizes, and the metrics leadership doesn't even know to ask for, this one's worth forwarding to your team and your founder. If you're making budget decisions, performance reviews, or strategy calls on numbers built before iOS privacy and bot click farms, you're probably operating on data that's lying to you.

EP 87: We pulled the data on every retention metric brands track, here are the 10 broken ones

Here's what they get into:

- The bot click problem nobody is correcting for

- How ESP attribution overcredits email and SMS

- Why revenue per recipient hides what actually drove the win

- Why industry benchmarks are mostly useless

- The LTV math almost every brand is doing wrong

- The metrics that predict program health (and nobody tracks)

Thank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

01:25 Why your retention metrics are quietly lying to you

03:22 Hot take 1: Open rates are fundamentally broken

06:30 Hot take 2: Click rates are inflated by bots too

10:28 Hot take 3: ESP attribution is mostly a fantasy

14:23 Hot take 4: Revenue per recipient hides more than it reveals

17:35 Hot take 5: List size is a vanity metric

20:46 Hot take 6: AOV is the wrong way to measure most campaigns

24:17 Hot take 7: Industry benchmarks are mostly garbage

27:46 Hot take 8: Your LTV math is wrong

32:09 Hot take 9: Unsubscribe rate isn't measuring what you think

34:48 Hot take 10: The metrics leadership doesn't know to ask for

38:27 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

After years of auditing retention programs, we're still seeing the same SMS mistakes.

In this episode of Send It, Jimmy Kim and Chase Dimond share 10 SMS hot takes based on years of working with ecommerce brands and auditing retention programs. From discount-driven opt-ins and over-sending to MMS strategy, segmentation, compliance, and deliverability, they break down what's actually working in SMS right now; and what brands should stop doing immediately.

EP 86: After auditing hundreds of brands, here are the 10 SMS mistakes we keep seeing

Here's what we're diving into:

- Why discount-driven SMS opt

-ins often create low-quality subscribers

- When MMS is worth the extra cost (and why most brands underuse it)

- How often brands should actually be sending SMS campaigns

- Why SMS segmentation should look different from email segmentation

- The biggest compliance and deliverability risks brands overlook

Thank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

03:07 Quick compliance disclaimer before we get into it

03:35 Hot take 1: Stop requiring a discount to get an SMS opt-in

07:04 Hot take 2: MMS beats SMS for revenue almost every time

09:44 Hot take 3: You should send way less SMS than you think

12:28 Hot take 4: Two-way SMS is overrated for most brands

16:34 Hot take 5: Transactional SMS is the most underrated surface in ecom

19:12 Hot take 6: SMS segmentation shouldn't look like email segmentation

22:21 Hot take 7: Keywords are wildly underused on SMS

26:18 Hot take 8: Most SMS compliance is theater

29:58 Hot take 9: Don't launch SMS until email is dialed in

33:49 Hot take 10: Stop using SMS for things email does better

36:08 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

The email "best practices" everyone repeats are quietly costing your brand real money.

In this episode, Jimmy Kim and Chase Dimond break down 10 hot takes on retention marketing that go against almost everything you've been told. From welcome series aggression to subject line strategy to why unsubscribes can actually be a good sign, they back every take with data and real-world experience across hundreds of brands.

EP 85: We read every email marketing best practice and ranked the 10 worst ones

Here's what they cover:

- Aggressive welcome series make more money and clean your list at the same time

- Subject lines and unsubscribes are tracked completely wrong by most marketers

- Over-segmenting, over-testing, and over-designing are quietly hurting performance

- Sending more often almost always beats sending less, when done with segmentation

- Black Friday strategy is overrated and copying competitors makes you invisible

Thank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

Lone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcast

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

03:12 Hot take 1: Aggressive welcome series win

06:06 Hot take 2: Subject lines aren't built for opens, they qualify

09:51 Hot take 3: Higher unsubscribes can mean higher revenue

14:28 Hot take 4: You're probably over-segmenting

18:07 Hot take 5: Your abandoned cart flow is too long

20:38 Hot take 6: A/B testing yourself into mediocrity

24:21 Hot take 7: Send more often, segment smarter

26:56 Hot take 8: Black Friday is overrated in its current form

30:11 Hot take 9: Email design matters less than you think

34:31 Hot take 10: Stop copying your competitors

37:53 Final thoughts and what to comment below

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

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https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

The 5-person retention team is on borrowed time.

In this episode of Send It, Jimmy Kim and Chase Dimond go on the record about something a lot of brands have been quietly doing for the last 12 months. The traditional retention pod (manager, two coordinators, designer, copywriter, SMS specialist) is getting restructured out of existence. CFOs are running the math, AI got actually good, and the tooling caught up.

The brands sending more email and making more revenue per send are doing it with one operator and a stack of AI tools, not a team of five. Jimmy and Chase walk through why this shift is happening, a day in the life of a 1-person operator, the four layer AI stack that makes it possible, and the five step playbook for becoming the operator brands actually want to hire in 2026.

EP 84: The death of retention teams how to operate as a 1 person army in 2026

Here's what they cover:

- The three forces (margin, AI quality, tooling) collapsing the traditional retention team

- What the 1-person retention operator actually spends their time on

- The four layer AI stack every solo operator should be running

- The real risks of going solo (burnout, tunnel vision, creative sameness) and how to protect against them

- The five step playbook for becoming the highest paid operator in retention

Thank you our friends at Omnisend, Superscale and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

01:11 Podcast Intro and Hot Take

02:25 Beauty Brand Case Study

05:00 Why Teams Are Restructuring

05:25 Force One Margin Pressure

08:41 Force Two AI Quality Leap

11:30 Force Three Tooling Maturity

15:08 One Person Retention Role

17:00 Four Core Jobs in 2026

20:24 Directing AI With Prompts

22:52 Quality Control and Brand Voice

26:05 AI Powered Performance Analysis

28:17 Compensation and Job Security

30:48 Brand Loaded AI Projects

34:33 Production Tools And Design

36:53 Analytics Feedback Loop

40:03 One Person Team Risks

41:17 Documentation And Backup Plans

43:08 Quality Drift And QA45:04 Tunnel Vision And Pushback

48:11 Creative Sameness Problem

50:25 Burnout And Community

52:00 Five Step Solo Playbook56:10 Final Recap And Wrap

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond\

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Letting AI hit send on your email program is how brands lose their list overnight.

In this episode of Send It, Jimmy Kim and Chase Dimond join Bernard Meyer, Omnisend's AI Operations Manager, to get on the record about what AI in email marketing actually looks like when it's working and where the fully autonomous fantasy falls apart. Brand voice drift, deliverability damage, and irreversible mistakes (mass suppressions, accidental deletions) are what happens when the human leaves the loop. The operators getting real lift are using AI as an assistant on skeletons, subject line variations, research, reporting, briefs, audits, and program analysis and feeding it real business data instead of asking it to hallucinate from scratch. Plus the three starter prompts every operator should run on day one.

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

Here's what they cover:

- Why fully autonomous AI sending is the fastest path to brand voice damage and deliverability loss

- The 7 high leverage tasks AI should actually be doing for your retention program

- What MCP is, why it matters, and how it turns generic AI output into business-aware analysis

- The three starter prompts (weekly snapshot, upsell segment recommendations, top-campaign pattern mining) that prove the stack works

- The 10 prompt pack giveaway and how to put human-in-the-loop guardrails around every AI workflow

Thank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

Lone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcast

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

02:37 AI as Tool Not Toy

05:00 Three Practical Uses

07:57 AI Hype to Ignore

12:16 Real Time Savings

16:09 Where Not to Trust

20:26 Data Ceiling and MCP Intro

23:01 Bernard Explains MCP

28:41 MCP Setup and First Prompts

30:40 Connect Omnisend in Claude

32:06 Weekly Snapshot Prompt Demo

36:08 Metrics That Matter Most

38:50 Upsell Segments From Buyer Data

41:12 When AI Gets Too Generic

43:37 Repeat Winning Campaign Patterns

47:48 Customer Data Access Guardrails

51:36 Human in the Loop Framework

54:30 Giveaway and Prompt Pack

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

A bad email gets ignored. A bad SMS gets you blocked.

In this episode of Send It, Jimmy Kim and Chase Dimond unpack why SMS keeps falling flat for so many brands and walk through the copywriting formulas that actually convert. The problem isn't the channel, it's that nobody learned how to write for it. With only 160 characters up for grabs, every word has to earn its place, every hook has to land in the first three seconds, and every send has to feel worth interrupting someone's day for. Jimmy and Chase break down the three part structure every high-performing SMS follows, the specific formulas for abandoned cart, replenishment, VIP drops, and flash sales, and the AI prompts they use to write and tighten copy fast.

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

Here's what we're diving into:

- Why SMS copywriting is a different skill than email and the four constraints that make it harder

- The hook → value → action formula every high-performing SMS follows

- Specific formulas for abandoned cart, replenishment, VIP drops, and flash sales

- The AI prompts they use to generate, compress, and A/B test SMS copy

- The frequency, segmentation, and testing rules that protect opt-out rates

Thank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

Lone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcast

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

02:57 Why SMS Is Different

03:25 Space And AI Compression

04:43 Context And Attention

05:39 Intimacy And Tone

06:43 Cost Frequency Segmentation

08:02 Hook Value Action Framework

10:48 Putting The Formula Together

13:27 Abandoned Cart Playbook

15:03 Replenishment Timing Texts

16:27 VIP Early Access Drops

17:06 VIP Drop Specifics

17:56 Flash Sale Formula

18:33 Mystery Discount Tests

19:59 AI Prompts For SMS

22:47 Prompt For Shortening

24:02 AI Variations For Testing

25:34 Replenishment Reminder Prompt

27:21 Testing Framework Basics

30:18 Common SMS Mistakes

31:40 Advanced SMS Tips

33:09 Final Recap And Wrap

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

AI didn't fail you... your prompt did.

In this episode of Send It, Jimmy Kim and Chase Dimond unpack why so many marketers are getting generic, unusable output from AI and walk through the prompt structure that fixes it. The problem isn't the tool, it's that nobody taught marketers how to talk to it. Most prompts are missing context, lack constraints, and leave AI guessing at the goal. They break down the four layer structure that turns vague requests into usable copy, then share the exact templates they use every day for subject lines, campaign ideation, body copy, brand voice training, SMS messages, and preview text.

EP 81: The 4 layer prompt structure that fixes bad AI output

Here's what they cover:

- The four layer prompt structure that turns lazy prompts into usable copy

- The subject line and campaign ideation prompts that produce real variety, not filler

- How to train AI on your brand voice using past winners and proven examples

- The body copy, SMS, and preview text prompts they use every single day

- The common prompt mistakes that produce bad AI output and how to fix them

Thank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

We're hitting the road! Join us for a private, half-day retention workshop coming to a city near you! Get tickets 20% off with ROADSHOW20:

https://commerceroundtable.com/roadshoweCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:55 Welcome To Send It

01:38 Prompts Matter Most

03:02 Four Prompt Layers

03:40 Layer One Context

04:57 Layer Two Task

05:37 Layer Three Constraints

08:21 Layer Four Format

09:29 Subject Line Prompts

11:36 Train With Past Wins

13:35 Curiosity Gap Testing

14:48 Campaign Idea Prompts

17:07 Pain Point Angles

18:51 Pain Point Prioritization

19:22 Seasonal Campaign Planner

20:16 Remix Past Winners

20:51 Email Body Copy Framework

23:01 AI As Copy Editor

24:28 Teach Brand Voice

25:43 SMS And Preview Text

28:26 Advanced Tips And Mistakes

30:31 Edit And Test Outputs

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

______

00:00 Welcome to the show

02:33 Meet Dimond Apparel: the mock brand we're auditing today

04:12 Prompt 1: the email program audit that ranks what's broken

06:55 Walking through the audit output and the top three priority fixes

09:58 Prompt 2: writing the actual flow emails with full subject line, preview text, and body copy

12:05 Prompt 3: the draft scoring workflow that catches what's not strong enough to ship

14:56 Prompt 4: writing subject lines that mix curiosity, urgency, social proof, and benefit

16:37 Prompt 5: building a 30 day campaign calendar w the right content mix

18:10 Prompt 6: running a competitor teardown to see where you stand in your category

20:30 Prompt 7: building the right segments and matching content to each

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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, 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

02:51 3 Most common welcome series pitfalls

08:56 The four email framework at a high level

12:46 The tactical breakdown of the four email timeline

13:26 Email 1: the welcome and how to deliver a quick win

15:00 Email 2: the education email and when to send it

16:41 Email 3: the recommendation email as a helpful guide

18:41 Email 4: the social proof email as your closer

21:27 The 7 to 10 day timing window and how to adjust it by category

23:16 What to do when subscribers buy partway through the series

24:23 How to test your welcome series the right way

30:08 Recap of the four email framework and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 paradox explained

04:47 What a healthy unsubscribe rate looks like in 2026

08:32 The benchmarks for a healthy email program

09:55 How fear of unsubscribes strips your brand of personality

13:06 Scenario 1: taking a stance on something controversial

14:19 Scenario 2: launching a new product or evolving your brand

16:23 Scenario 3: intentionally cleansing your list with re-engagement

18:57 The four metrics that matter more than your unsubscribe rate

20:10 Why the best brands are willing to be polarizing

21:39 The unsubscribe rate benchmark cheat sheet

25:23 The hot take: unsubscribes are not the enemy, boring is

25:48 Recap & final thoughts of the unsubscribe paradox

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

The agency vs in-house debate has burned more brands than it has built.

In this episode, Jimmy Kim and Chase Dimond break down the real decision framework behind one of the most loaded questions retention marketers, founders, and execs ask: should you hire an agency or build the team in-house? They get into when an agency actually makes sense, what you should never outsource, the hybrid model that works at scale, and the red flags that mean it's time to part ways.

EP 77: Agency vs in house: when to hire, when to 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 outsource

13:18 Protecting your brand voice

15:21 The hybrid model that actually works

18:21 Red flags that mean it's time to fire them

23:44 The gatekeeping knowledge problem

24:24 A four-question framework to make the call

27:09 Recap and final takeaways

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Creative used to be the bottleneck. It doesn't have to be anymore.

In this episode of Send It, Jimmy Kim and Chase Dimond get tactical about how retention marketers can use AI to completely change how they produce email and SMS content.

Not the vague "just use ChatGPT" advice, but the actual workflow, the brief structure, the editing process, and the quality control system that lets you go from a four hour campaign to a 30 minute one without your emails sounding like they were written by a robot. They also get honest about where AI still falls short and what it means for the future of retention marketing.

EP 76: How to produce 5x more email and SMS content with 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 HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://inboox.ai/

______

00:00 Welcome to the show

04:34 The old workflow and why it takes three to four hours per campaign

06:18 How AI compresses the creative timeline

10:13 The four layers where AI actually helps the retention workflow

15:40 The five step workflow: start with a brief, not a blank prompt

19:00 Idea generation and picking the best campaign angles

22:07 Creating test variations from your edited base email

22:44 How to prevent AI content from feeling robotic or generic

25:52 The study, adapt, generate framework for better AI inputs

30:40 What AI still can't do: brand voice nuance, strategy, and customer insight

33:07 The future: mass personalization and content velocity at scale

35:17 Recap of everything covered and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Bad tests don't just waste time. They send you in the wrong direction with confidence.

In this episode of Send It, Jimmy Kim and Chase Dimond break down why traditional email testing is broken in 2026; and exactly how to fix it. Between Apple's Mail Privacy Protection inflating open rates and smaller segments making statistical significance harder to reach, the old way of testing leads to bad decisions disguised as data. This episode is the updated framework that actually works right now.

EP 75: Creative testing that actually works in 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 much harder in 2026

04:05 How Apple MPP destroyed open rate as a reliable testing metric

05:20 The metrics you should actually be testing against

08:16 The one variable rule and why it matters

10:25 Layer 1: Positioning - the highest leverage test most brands skip

12:10 Layer 2: Structure - how the email is built and why it matters

14:15 Layer 3: Creative - where most brands start but shouldn't

15:21 Layer 4: Timing - when to send and why it matters for certain emails

16:16 How to test effectively when your list is small

20:45 Building a creative library that makes every future test smarter

23:50 Learning velocity: why the best teams learn faster than everyone else

27:58 The HCE framework: hypothesis, control, evaluate

30:13 Recap of everything and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Retention isn't about technology. It's about human behavior.

In this episode of Send It, Jimmy Kim and Chase Dimond get into the six psychology principles behind why people actually buy. From reciprocity to momentum, these are the human behavior triggers that the best retention programs are built on… and most brands aren't using any of them intentionally.

If you've ever wondered why a technically good email still doesn't convert, this episode is going to change the way you think about every message you send.

EP 74: Conversion psychology: 6 principles for retention 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 before you ask

06:50 Principle 2: Urgency - how to use it without losing credibility

10:44 Principle 3: Friction removal - every email should remove at least one barrier

15:20 Principle 4: Curiosity gaps - the subject line technique most brands get wrong

19:55 Principle 5: Identity and belonging - sell who your customer wants to be

25:30 Principle 6: Momentum - how small actions lead to big purchases

28:27 A simple framework for applying all six principles to any campaign or flow

29:45 A real email breakdown that hits multiple psychology principles at once

30:43 Recap of all six principles and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Most brands switch ESPs and lose months of sender reputation in a single send. It doesn't have to go that way.

In this episode of Send It, Jimmy Kim and Chase Dimond draw from over 1,000 personal ESP migrations to walk through the exact five step warmup framework brands should follow when switching platforms. From setting up a fresh sending domain to segmenting smarter than 90 day openers, this is the most practical deliverability episode we've done.

EP 73: Our 5 step ESP migration warmup 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 settings before you send anything

11:24 Step 3: Getting your store integration right

15:06 Step 4: Building your segmentation strategy for warmup

20:09 Step 5: How to sequence your daily sends during warmup

24:34 The metrics that tell you your warmup is actually working

28:31 What to do when deliverability drops mid warmup

30:06 How to diagnose a technical issue vs a burnt domain

31:26 DIY migration vs working with a professional

33:40 Recap of all five steps and final thoughts

_____

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Discounts feel like the easy button. But every time you hit it, you're training your customers to wait for a sale… and slowly destroying your margins in the process.

In this episode of Send It, Jimmy Kim and Chase Dimond break down the discount death spiral that most DTC brands are stuck in, and walk through five actionable frameworks for driving repeat purchases without ever needing to slash your prices. From loyalty programs that actually create status to content sequences that build confidence between purchases, this episode is a practical playbook for brands that want to compete on value; not price.

Whether you're trying to wean customers off discounts or build a retention strategy from scratch, these frameworks work at any stage.

EP 72: Why discounts are hurting your brand and what to do 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://www.ecomemailcertified.com/

Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://inboox.ai/

______

00:00 The discount addiction nobody wants to talk about

02:35 The discount death spiral explained

05:10 Framework 1: Building a loyalty program with real value beyond points

10:43 Framework 2: Bundling to sell outcomes not just products

15:59 Framework 3: Using exclusivity and early access to create urgency without discounting

17:56 The four step drop strategy broken down

20:36 The campaign sequence for an exclusive early access drop

22:01 Framework 4: Content micro-wins and why this is the most underrated retention lever

26:23 Framework 5: Winning on convenience and service instead of price

31:13 What a no discount retention calendar looks like week to week

33:01 Recap of all five frameworks and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

What do owls, Drake, and 74,000 "exclusive" subject lines all have in common? They all showed up in email marketing data from 2025.

In this episode of Send It, Jimmy Kim and Chase Dimond take a break from the serious stuff and dig into a fun data report from our partners at Omnisend. They review the emojis, celebrities, pop culture moments, holidays, animals, and overused cliches that dominated email campaigns throughout the year.

The results are equal parts funny, surprising, and honestly pretty revealing about how email marketers think.

Check out Omnisend’s full report here: https://www.omnisend.com/email-fun-facts-year-in-review-2025/?utm_source=SendIt&utm_medium=Promo 

Here's what we're getting into:

• The top 10 most used emojis in subject lines (the number one will surprise you)
• Which celebrities got name-dropped most - and why Drake topped the list
• The TV shows and movies marketers referenced most
• Why owls beat dogs and cats as the most mentioned animal
• The internet culture moments brands actually leaned into
• Most mentioned holidays and whether the order matches the revenue
• The overused cliches showing up in thousands of campaigns
• Why "exclusive" appeared in over 74,000 campaigns
• The 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 fastest-growing Shopify brands. https://inboox.ai/

______

00:00 Welcome to The Show

03:44 The top 10 most used emojis in subject lines revealed

08:43 The TV shows and movies marketers referenced most

11:50 The most mentioned animal in email (it's not a dog or cat)

15:54 Internet culture moments brands actually leaned into

16:39 Protein, matcha, Stanley and the pop culture keywords of 2025

17:46 Viral moments that made it into email campaigns

20:12 How many brands actually talked about tariffs and politics

21:59 The holiday calendar every email marketer is working from

23:51 The worst marketing cliches showing up in thousands of campaigns

25:14 Why "exclusive" is everywhere and how much of it is AI

28:19 The oops and apology email - mistake or marketing tactic

30:12 How 82% of marketers start their emails

31:43 Final thoughts and where to find the full report

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

There's a reason some brands keep growing and others plateau… and it usually shows up in their retention strategy first.

In this episode of Send It, Jimmy Kim sits down with Feras Khouri, co-founder of New Standard Agency, to break down six things that 8 and 9-figure DTC brands consistently do in email and SMS that most brands overlook. Feras brings a rare perspective having scaled his own brand to 8 figures before building an agency that now works with some of the biggest names in DTC including AG1, Caraway, and New Era Caps. They also get into why email attributed revenue can actually be a warning sign, and what it really means when your year-over-year numbers start to slip.

Whether you're at 7 figures or 9, the principles here are the same. The brands that win aren't just sending more emails. They're thinking about retention as a system.

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

02:00 Meet Our Guest: Feras's Khouri

05:00 Does this apply to smaller brands? The 7-figure vs 8-figure question

10:00 #1: Set retention-specific goals

14:00 #2: Understand layer two metrics

17:00 #3: Look beyond email and SMS

22:00 #4: Use retention for acquisition

27:00 #5: Create an internal feedback loop

37:00 #6: Rapidly test technology

41:00 Building a brand brain with AI vs. using AI to replace human thinking

44:00 Wrap up, where to find Feras, and final thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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 brands. https://inboox.ai/

______

00:00 Why Most Brands Are Using AI Wrong

01:40 From Finance to Founder: How Phil Built His Edge

07:30 The 8-Figure Brand Advantage (And What Smaller Brands Miss)

10:39 Where AI Actually Saves Time (Process + Design Workflows)

12:58 The Truth About AI Copy: Brainstorming vs. Original Thinking

15:02 Why Voice, Hooks, and Angles Still Win

16:42 The Real Differentiator in 2026: Taste + Ideas

19:43 Using Gemini to Align Copy and Design Faster

20:41 The ESP Data Trap (And Why History Can Hurt You)

21:46 The Power of “In-Between” Campaigns (Beyond Sales)

24:05 Why Retention Still Needs Humans

25:11 Click Strategies That Don’t Rely on Discounts

26:24 Super Bowl SMS Drop + Valentine’s Click Case Study

33:56 Will We Be Emailing AI Agents? The 5–10 Year Outlook

37:16 Final Takeaways: What Actually Matters

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Acquisition is harder. CAC keeps climbing. Attribution feels like guesswork.

The brands still growing profitably are not “sending more” to fix it. They’re building retention systems that move customers forward, one step at a time.

In this episode of Send It, Jimmy Kim and Chase Dimond teach a practical 8-step retention framework built from real brand work and Omnisend benchmark data. You’ll also get a downloadable worksheet to map your customer journey, audit your lifecycle gaps, and turn retention into something repeatable.

This is not a “run more campaigns” episode. It’s how to build a retention engine that makes revenue more predictable.

Download the worksheets here: https://cdn.prod.website-files.com/6735048599b05e098e178c8f/6952c64d53f794174c3fa62d_Retention%20Redefined%20Worksheets.pdf Access

Omnisends full report here: https://www.omnisend.com/resources/reports/2026-ecommerce-marketing-report/?utm_source=SendIt&utm_medium=Promo

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

04:04 The Importance of Retention Marketing

09:58 The Modern Customer Journey

15:06 Effective Segmentation Strategies

18:37 Channel Pairing: Email and SMS

21:05 Leveraging AI in Retention Marketing

25:11 Personalizing Messages at Scale

26:52 Optimizing Key Flows for Retention

28:35 Advanced Retention Strategies

32:58 Metrics That Matter in 2026

39:35 Implementing a 90-Day Retention Plan

42:19 Final Thoughts and Resources

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Open rates are inflated. Clicks are misleading. And inbox algorithms don’t reward surface-level engagement anymore.

In this episode of Send It, Jimmy Kim and Chase Dimond break down why traditional email and SMS metrics are failing eCom teams; and what you should be tracking instead as inbox rules, privacy changes, and AI filtering reshape how messages get seen.

Optimizing for opens and clicks can feel productive, but it often leads brands to make confident decisions based on incomplete signals. This episode introduces a modern measurement framework built around real behavior, intent, and revenue impact (not vanity metrics).

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

Here's what we're diving into:

- Why open rates are inflated, unreliable, and no longer decision-worthy

- How inbox providers now use engagement as a visibility signal

- The 4-layer engagement stack top brands are adopting

- Which metrics actually prove retention impact to leadership

- How to rethink attribution without chasing “perfect” numbers

- What to move to the top of your KPI dashboard (and what belongs at the bottom)

Thank you our friends at Omnisend, Inboox and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/

eCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

Explore Inboox.ai, the AI-powered database of 1M+ real ecommerce emails with full HTML, performance data, and trend insights from the fastest-growing Shopify brands. https://inboox.ai/

______

00:00 Welcome to The Show

02:21 Redefining Engagement Metrics

02:54 Impact of Privacy and AI on Email Marketing

04:37 New Requirements from Google and Yahoo

05:43 Gmail's Algorithm and Engagement

07:38 The Shift to Quality Over Quantity

11:49 Building a Real Engagement Stack

14:50 Key Email Metrics

15:23 SMS Metrics Overview

16:04 Customer Behavior Insights

17:24 Business Outcomes Metrics

20:05 Challenges in Attribution

25:01 Actionable Steps for Improvement

28:32 Conclusion and Wrap-Up

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Most brands only segment by openers and VIPs… then wonder why email performance stalls.

In this episode of Send It, Chase Dimond and Jimmy Kim dive into 12 powerful email and SMS segments that go beyond the basics and actually boost conversions, protect margins, and reduce fatigue. These aren’t theory; they’re tried and true segments top DTC brands use to send smarter.

You’ll learn how to segment based on intent, behavior, timing, and risk; so every message feels more personal, more relevant, and more profitable. Whether you’re scaling a list or trying to squeeze more ROI from your existing subscribers, this framework will help you unlock smarter strategy and cleaner results.

EP 66: 12 Unusual segments that drive serious eCommerce 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 Discount Rejectors

11:25 Product Loyalists

13:05 Risky First-Time Buyers

15:09 High AOV, Low Frequency Buyers

16:55 Engagement Only Buyers

19:02 Seasonal Only Buyers

21:58 Promo Only Buyers

23:43 Reactivating Recently Lapsed High-Value Buyers

25:26 Engaging Multi-Category Explorers

26:56 Converting Subscription-Adjacent Buyers

29:28 Recognizing and Rewarding Brand Advocates

33:39 Understanding and Targeting Silent VIPs

35:37 Tips for Implementing Segmentation Strategies

40:27 Recap and Final Thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

The biggest mistake most brands make? They think retention starts after the first sale.

In this episode of Send It, Jimmy Kim and Chase Dimond break down why the real retention window starts the moment someone joins your list (not when they buy).

You’ll learn how to design your first 45-day subscriber journey to build trust, deliver micro-wins, and turn subscribers into repeat customers. Plus, we break down habit loops, lifecycle stages, and the overlooked “repeat trigger window” that keeps customers coming back.

EP 65: Why the first 45 days matter more than the first 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 Importance of Repeat Trigger Windows

29:26 Proactive vs. Reactive Messaging

31:51 Calculating and Utilizing Repeat Trigger Windows

34:05 Bringing It All Together: A Cohesive Strategy

36:28 Conclusion and Recap

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

We got early access to Omnisend’s 2025 ecommerce report and the numbers will change how you think about your email and SMS strategy.

Based on 41 billion+ messages from over 160,000 ecommerce brands, this isn’t a survey or projection; it’s real customer behavior data. What did we learn? Most brands are optimizing for the wrong things.

In this episode, Jimmy and Chase break down the data that proves automations destroy campaigns on performance, why transactional emails are secret revenue engines, and how top brands quietly grew 200% while others shrank.

Grab Omnisend’s full report here: https://www.omnisend.com/2026-ecommerce-marketing-report/?utm_source=SendIt&utm_medium=Promo

EP 64: What we learned from 41 billion emails sent in 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 Transactional Emails: Untapped Potential

12:24 Preparing for Q4: Strategies and Insights

16:44 The Role of SMS in Marketing

17:57 SMS Campaigns vs. Automations

21:31 Optimizing SMS for eCom

24:34 Order Growth Insights

26:22 Global eCom Trends

27:30 Fundamentals of Automation

35:35 Campaigns vs. Automations

39:22 Final Takeaways and Recommendations

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Struggling with retention but not sure what’s broken?

In this episode, Jimmy Kim and Chase Dimond walk through their 7-part retention audit framework used to diagnose DTC brands in 60 minutes or less.

Whether you’re an agency, operator, or founder, this episode breaks down how to find revenue leaks, fix deliverability, improve your flows, and benchmark your lifecycle strategy against the best in the game.

You’ll learn how to check your data plumbing, uncover hidden issues in your segmentation, and rebuild an email + SMS program that actually works.

EP 63: The retention audit: How to diagnose any brand in 60 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 Effective Segmentation Strategies

26:43 Crafting Mobile-Optimized Emails

31:08 Enhancing Customer Experience Beyond Emails

35:47 Analyzing Metrics for Better Retention

37:56 Final Thoughts and Recap

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Most brands obsess over open rates, but ignore the most misleading metric in their dashboard: clicks.

In this episode, Jimmy Kim and Chase Dimond break down the truth about email and SMS click tracking. From accidental taps to bot activity to real buyer intent, not every click means the same thing. But most ESPs lump them all together, inflating your metrics and misleading your decisions.

Jimmy and Chase share a clearer framework for identifying click quality, improving attribution, and optimizing for real engagement; not just vanity numbers.

Plus, we introduce eClickTrack, our new link-tracking tool built for ecommerce brands who want to see real, human engagement, not bots.

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

07:45 Driving High-Quality Clicks

13:12 Challenges with Click Data

15:39 The Problem with Bot Clicks

17:01 Common Email Marketing Mistakes

19:58 Key Features of E Click Track

26:06 Optimizing Click Quality in Email Campaigns

28:59 Final Thoughts and Recommendations

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

AI just predicted the future of retention marketing… but is it accurate?

In this episode, Jimmy Kim and Chase Dimond ask ChatGPT to generate bold 2026 predictions for ecommerce email and SMS marketers and then break down what they agree with, what’s BS, and what might already be happening.

From segmentation going predictive to retention teams owning margin and profit, this episode is packed with strategic insights and real-world examples from brands, agencies, and operators doing the work.

EP 61: Here's what AI says about retention marketing in 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 The Future of Preference Centers

23:37 Profit Accountability for Marketers

25:27 Retention Marketers and Replenishment Control

29:13 Job Security Tied to Returning Customers

31:15 The Role of AI in Marketing

34:59 Conclusion and Final Thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Gmail just rolled out the biggest inbox overhaul in years and it’s about to change how every ecommerce brand sends email.

In this episode, Jimmy Kim and Chase Dimond break down the new Gmail features that are shaking up deliverability, unsubscribe rates, and how messages show up in the Promotions tab.

They cover everything from the new Manage Subscriptions view (which ranks senders by frequency and makes unsubscribing easier than ever) to Postmaster Tools v2 and Google’s new compliance enforcement rules for bulk senders.

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

11:27 Gmail's New Purchase View

17:42 Promotions Tab Overhaul

19:10 Gmail's New Relevance Ranking System

22:08 Strategies for Improving Email Engagement

26:37 Technical Changes in Gmail's Postmaster Tools

29:24 Compliance and Enforcement for Bulk Senders

36:05 Summary and Key Takeaways

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

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https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

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, performance data, and trend insights from the fastest-growing Shopify brands. https://e.eemtrk.com/r/sendit-inboox

______

00:00 Welcome to The Show

01:15 The Importance of BFCM Buyers

02:42 Maximizing Post-BFCM Engagement

03:10 Understanding BFCM Buyer Behavior

06:52 Effective Follow-Up Strategies

10:12 Tactical Campaign Ideas

20:33 Key Metrics to Track

23:44 Conclusion and Final Thoughts

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Most brands blow their budget on BFCM and then ghost their best customers.

In this episode of Send It, Jimmy Kim and Chase Dimond break down what happens when you go silent after Black Friday and how to fix it. You’ll learn how to turn high-intent, one-time buyers into loyal, high-LTV customers using a proven 4-stage retention strategy.

They share the campaigns to send, the exact follow-up timing, and 5 post-BFCM metrics to track to keep your Q4 profitable after the sale.

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

Here's what we're diving into:

- Why second purchases are the key to post-BFCM profitability

- The biggest mistake brands make after Black Friday

- A 4-stage post-purchase flow: onboarding, education, bridge offer, nurture

- 5 plug-and-play campaigns to send right now

- The metrics that matter: time-to-second-purchase, flow conversion, and 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 Common Mistakes Brands Make Post-BFCM

12:50 Stage One: Onboarding Emails

14:16 Stage Two: Educational Content

15:29 Stage Three: The Bounce Back Offer

17:40 Stage Four: Long-Term Nurture

18:49 Effective Email Campaigns

23:48 Metrics to Track Post BFCM

28:56 Final Recap and Closing Remarks

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

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Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

What's the perfect email cadence? Daily, weekly, or just when you have something to say?

In this episode, Jimmy and Chase break down the pros and cons of different email frequencies (daily sends, weekly campaigns, and launch-only strategies) and help you figure out what cadence is right for your brand.

They share real examples, revenue-impacting data, and a step-by-step framework to test and dial in your ideal email frequency; without burning your list or obsessing over unsubscribes.

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

Here's what we're diving into:

- Daily vs. weekly vs. campaign-based sending (and what actually works)

- A real-world test: 2 emails/week vs. 5 emails/week (+70% revenue)

- Why open rates and unsubscribes matter less than you think

- 5 factors that determine the right cadence for your brand

- How to segment your list by frequency without overwhelming subscribers

- The “steady + burst” strategy top brands use to scale email without 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

14:00 Unsubscribes, Open Rate Myths & What Actually Drives Revenue

18:40 5 Factors That Determine the Right Cadence

22:00 Segmenting by Frequency (VIPs vs Unengaged)

23:15 Smart Suppression & Total Email Count

25:00 Red Flags That You're Over-Sending

28:30 Your Email Cadence Optimization Playbook

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

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Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

The biggest week in ecommerce is the one everyone forgets.

In this episode, Jimmy Kim and Chase Dimond break down one of ecommerce’s best-kept secrets: Q5. The week between Christmas and New Year’s that quietly drives massive revenue for brands that don’t go dark.

Most brands shut off campaigns after BFCM, but consumers aren’t done buying. They’ve got gift cards, return credits, and “treat yourself” energy. That’s your big window.

Jimmy and Chase reveal exactly how to plan, message, and automate your Q5 campaigns so you can capture the easiest money of the year while your competitors are on vacation.

EP 56: The secret quarter most brands ignore (Q5)

Here's what we're diving into:

- Why Q5 works (returns, gift cards, and self-gifting behavior)

- 4 winning campaign angles: encore sale, gift card push, self-care, flash sale

- How to message Q5 differently from BFCM

- The ideal Q5 cadence for email + SMS (with examples)

- How to automate everything before Dec 26 and still cash in

- What NOT to do (hint: stop copy-pasting your Black Friday sale)

Thank you our friends at Omnisend, Kintsugi and eCom Email Certified for sponsoring the podcast!

Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://eemtrk.com/omnisend-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 Introduction to Q5: The Secret Fifth Quarter

02:36 Understanding Q5: Why It Matters\

04:12 The Q5 Playbook: Strategies for Success

10:32 Promotional Strategies for Q5

15:38 Flash Sales and What Not to Do During Q5

17:55 Meeting Customers Where They Are

18:24 Creative Angles for Post-Holiday Marketing

20:45 Optimizing Email and SMS Cadence

25:21 Automating Q5 Campaigns

30:21 Q5 Checklist and Best Practices

33:10 Final Thoughts and Promotions

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

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https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

Ever wondered what Jimmy and Chase are up to behind the scenes?

In this episode, the duo reflect on their first year of partnership and pull back the curtain on what they’re building next… two new tools designed to change the way ecommerce brands do retention marketing.

From analyzing millions of emails to redefining attribution, they break down how Inboox.ai and eClickTrack are solving the biggest problems email and SMS marketers face today: lack of visibility, disconnected data, and shallow insights.

Pull up a seat because Chase and Jimmy are breaking down their roadmap for the next wave of retention marketing tools.

EP 55: Why we’re betting big on retention tools

Here's what we're diving into:

- The vision behind Inboox.ai and why it’s the “search engine” for ecommerce emails

- How eClickTrack will give marketers real attribution clarity without iOS blind spots

- Lessons from scaling media, agencies, and SaaS under one retention brand

- Why retention marketing needs smarter data, not louder campaigns

- The future of ecommerce tech stacks in a post-BFCM world

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 — Intro + Behind the Scenes

02:00 — The Vision: Building the Future of Retention Marketing

05:00 — The Origin of eClickTrack

10:15 — Solving Bot Clicks + Real Attribution

13:00 — Use Cases: Creators, Brands, and Agencies

19:45 — Introducing Inboox.ai

23:45 — The AI Breakdown: Email Analysis Engine

26:30 — Who It’s For

30:30 — Pricing + Agency Collaboration Tools

32:00 — Closing Thoughts + Next Steps

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

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https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!

What if 80% of your email revenue comes from just 20% of your effort?

In this episode, Jimmy Kim and Chase Dimond unpack the real data behind ecommerce email performance; revealing the flows, segments, and campaigns that actually move the needle (and the ones you can delete today).

They’ll show you how to stop over-engineering your automations, focus on the top-earning flows, and simplify your email strategy to drive more revenue with fewer sends. If you’ve ever felt overwhelmed by 47 flows, endless A/B tests, or bloated lists, this episode is your reset button.

EP 54: The 80/20 of Email Revenue: How to Double Your ROI by Doing Less

Here's what we're diving into:

- The 3 flows that drive 60–80% of automated revenue (and how to optimize them)

- The segments that matter: VIPs, one-time buyers, and engaged subscribers

- Why your welcome and sunset flows don’t deserve your energy

- Campaign types that convert - and how to balance promo vs. content sends

- The metrics that matter in 2025 (hint: it’s not open rates)

- How to cut 50% of your email workload and still grow faster

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

02:14 The 80/20 Rule in Email Marketing

04:24 Key Revenue-Generating Email Flows

10:13 The Power of Post-Purchase Flows

12:21 The Importance of Browse Abandonment

13:28 Overrated Email Flows

16:16 High-Value Segments in Email Campaigns

21:15 Segments That Don't Matter: Avoiding Common Pitfalls

24:31 Effective Campaign Strategies

28:15 What Not to Send: Avoiding Common Mistakes

35:47 The 80/20 Rule: Simplifying for Success

______

Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!