Send It!

You can be great at getting people into a subscription, but if they churn after a few cycles, all you’ve built is a leaky bucket. Jimmy Kim and Chase Dimond break down how to plug the leaks in Part 2 of our subscription and replenishment series.

If you missed Part 1 (how to get customers in), watch it here: https://youtu.be/AXgvrdeBpSk

What we cover:

→ Voluntary vs. involuntary churn, and why a big slice of your churn isn’t a decision at all

→ Dunning: pre-dunning, smart retries, card account updaters, and the “update your card” message

→ The real reasons subscribers cancel, and a fix for each one

→ Save offers that work: pause, skip, swap, adjust frequency, and downgrade

→ Why making cancellation a maze burns your brand

→ How to prevent churn before anyone reaches the cancel button

→ Why churned subscribers are one of your warmest win-back targets

→ The metrics that matter: voluntary vs. involuntary churn, churn by cycle, and failed payment recovery rate

If you only do one thing this week: check your failed payment recovery, or find out whether you have a dunning setup at all.

[object Object]Thank you our friends at Omnisend, Retention and Allan for the sponsorship!

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

Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast

Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/

Want to learn more about all things email and sms marketing?

Chase and I have a master course:

eCom Email Certified is 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

[object Object]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/

CHAPTERS

00:00 Intro

00:46 Welcome to Part 2

02:06 Two Types of Churn

03:24 Dunning and Failed Payments

07:01 Sponsor: Omnisend

08:54 Why Subscribers Cancel

10:27 Save Offers: Pause, Skip, Swap

13:23 Sponsor: Retention.com

14:07 Cancel Flow Ethics

15:27 Prevent Churn Before It Starts

20:03 Win Back Churned Subscribers

21:13 Sponsor: Allan

22:54 Metrics That Matter

24:44 Wrap Up and Next Steps

#subscriptionmarketing #churn #retentionmarketing #ecommerce #emailmarketing #smsmarketing

[object Object]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 bolt a “Subscribe & Save” widget onto a product page, watch nobody use it, and decide subscription doesn’t work for them. Jimmy Kim and Chase Dimond argue the real problem is that they never understood what they were building.

This is Part 1 of a two-part series on recurring revenue for consumable brands. Today is about getting customers in. Next week is about keeping them.

What we cover:

→ The difference between subscription and replenishment (and why most consumable brands need both)

→ When subscription actually fits your product, and when forcing it makes churn worse

→ Why offering a subscription at first purchase churns faster, and when to offer it instead

→ Why you shouldn’t sell subscription on the discount alone

→ Non-price levers that make a subscription attractive: free shipping, bonuses, early access, flexibility

→ How to build a replenishment reminder around your product’s natural consumption cycle

→ Why one-tap reordering matters more than clever copy

→ How to use replenishment as the on-ramp that feeds your subscription program

If you only do one thing this week: find the percentage of your repeat buyers on subscription vs. reordering manually, and your product’s natural reorder cycle.

______

Thank you our friends at Omnisend, Retention and Allan for the sponsorship!

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

Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&utm_medium=podcast

Allan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://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

______

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/

#subscriptionmarketing #replenishment #ecommerce #retentionmarketing #emailmarketing #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.

CHAPTERS

00:00 Welcome to Send It

00:54 Two Part Subscription Series

02:16 Subscription Versus Replenishment

05:24 When Subscription Fits

07:04 Sponsor: Omnisend

08:39 Where to Offer Subscription

11:31 Beyond Discounts

14:24 Replenishment Timing Playbook

17:26 Sponsor: Allan

19:14 Bridge to Part Two

20:25 Key Takeaways and Homework

22:24 Outro

______

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!

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/

______

#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

______

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/

______

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

______

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/

______

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/

______

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/

______

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/

______

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

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!

(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:

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!

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

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!

(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/

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!

(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

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!

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

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

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 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

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

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

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

Follow Chase Dimond at:

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(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/

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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

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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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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/

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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

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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!