Send It!

(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on Black Friday and Cyber Monday, and why most of the advice retention marketers have followed for five years is now outdated or actively working against them.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:

https://x.com/yojimmykim

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

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Follow Chase Dimond at:

https://x.com/ecomchasedimond

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Unlock true 1:1 personalization: https://ecomemailmarketer.com/send-it/personalization-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 [email protected] 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.tiktok.com/@chasehunterdimond

Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Download our 4-part briefsheet for better AI prompts >> www.ecomemailmarketer.com/ai-prompt-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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Follow Chase Dimond at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

(Free download) Steal our notes from the Retention Roadshow: https://ecomemailmarketer.com/notes-from-retention-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 [email protected] for sponsorships, appearance requests, interviews, or general information!

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

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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 [email protected] for sponsorships, appearance requests, interviews, or general information!

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

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

EP 86: After auditing hundreds of brands, here are the 10 SMS mistakes we keep 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 [email protected] for sponsorships, appearance requests, interviews, or general information!

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

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

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

Here's what they cover:

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

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

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

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

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

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

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

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

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

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

______

00:00 Welcome to the show

03:12 Hot take 1: Aggressive welcome series win

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

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

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

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

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

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

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

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

34:31 Hot take 10: Stop copying your competitors

37:53 Final thoughts and what to comment below

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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

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

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

Follow Chase Dimond at:

https://x.com/ecomchasedimond

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

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

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

Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The 5-person retention team is on borrowed time.

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

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

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

Here's what they cover:

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

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

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

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

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

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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/

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Follow Jimmy Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

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

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

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

Here's what they cover:

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

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

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

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

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

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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

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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:

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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 [email protected] for sponsorships, appearance requests, interviews, or general information!