Send It!

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

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

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

Here's what we're diving into:

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

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

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

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

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

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

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

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

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

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

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02:57 Why SMS Is Different

03:25 Space And AI Compression

04:43 Context And Attention

05:39 Intimacy And Tone

06:43 Cost Frequency Segmentation

08:02 Hook Value Action Framework

10:48 Putting The Formula Together

13:27 Abandoned Cart Playbook

15:03 Replenishment Timing Texts

16:27 VIP Early Access Drops

17:06 VIP Drop Specifics

17:56 Flash Sale Formula

18:33 Mystery Discount Tests

19:59 AI Prompts For SMS

22:47 Prompt For Shortening

24:02 AI Variations For Testing

25:34 Replenishment Reminder Prompt

27:21 Testing Framework Basics

30:18 Common SMS Mistakes

31:40 Advanced SMS Tips

33:09 Final Recap And Wrap

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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

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

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

Follow Chase Dimond at:

https://x.com/ecomchasedimond

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

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

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

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

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

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

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

Here's what they cover:

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

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

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

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

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

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

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

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

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

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

______

00:55 Welcome To Send It

01:38 Prompts Matter Most

03:02 Four Prompt Layers

03:40 Layer One Context

04:57 Layer Two Task

05:37 Layer Three Constraints

08:21 Layer Four Format

09:29 Subject Line Prompts

11:36 Train With Past Wins

13:35 Curiosity Gap Testing

14:48 Campaign Idea Prompts

17:07 Pain Point Angles

18:51 Pain Point Prioritization

19:22 Seasonal Campaign Planner

20:16 Remix Past Winners

20:51 Email Body Copy Framework

23:01 AI As Copy Editor

24:28 Teach Brand Voice

25:43 SMS And Preview Text

28:26 Advanced Tips And Mistakes

30:31 Edit And Test Outputs

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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

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

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

Follow Chase Dimond at:

https://x.com/ecomchasedimond

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

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

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

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

Your email program has problems. AI can find them in 5 minutes.

In this solo episode of Send It, Chase Dimond walks through seven AI prompts that completely change how email marketers, agencies, and freelancers run their programs. Chase shows exactly how to audit an entire email setup, rewrite the flows that aren't working, build a 30 day calendar that mixes the right content, run a teardown of your competitors, and segment your list the right way.

EP 80: The 7 AI prompts every email marketer needs

Download all the prompts here >> https://ecomemailmarketer.com/ai-prompt

Here's what he covers:

- The mock brand setup and the real numbers behind the audit example

- How to interpret the audit output and pick the top three fixes to focus on

- 7 AI prompts to audit, rebuild, rewrite, and optimize your systems

- The AI rules every marketer needs to follow: editing, fabrication, and hype claims

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

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

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

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

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

______

00:00 Welcome to the show

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

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

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

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

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

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

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

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

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

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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

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

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

Follow Chase Dimond at:

https://x.com/ecomchasedimond

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

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

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

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

A 14 email welcome series isn't a strategy... It's a slow goodbye.

In this episode of Send It, Jimmy Kim and Chase Dimond break down why so many welcome series quietly underperform and walk through the four email framework that consistently turns subscribers into customers. They get into the psychology behind first-time buyers, the four questions every welcome series needs to answer, and the timing logic that unlocks conversions. If your welcome series is doing all the talking and none of the converting, go ahead and hit play.

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

Here's what we're diving into:

- Why long welcome series quietly tank your conversion rate and LTV

- The "we, we, we" trap that makes brands talk past their new subscribers

- Why leading with a discount trains the wrong buying behavior from day one

- The four psychological questions every welcome series needs to answer

- Why testing for LTV beats testing for conversion rate every time

- The four mistakes that quietly kill welcome series performance

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

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

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

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

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

______

00:00 Welcome to the show

02:51 3 Most common welcome series pitfalls

08:56 The four email framework at a high level

12:46 The tactical breakdown of the four email timeline

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

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

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

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

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

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

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

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

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

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

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

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

Follow Chase Dimond at:

https://x.com/ecomchasedimond

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

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

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

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

A 0.1% unsubscribe rate isn't the flex most marketers think it is.

In this episode of Send It, Jimmy Kim and Chase Dimond take on one of the most misunderstood metrics in email marketing and make the case that obsessing over unsubscribes is quietly making your program worse. They walk through why playing it safe produces generic content, how a low unsubscribe rate can actually be a warning sign, and why the healthiest email programs are the ones willing to lose a few people every week. This one is a mindset reset for anyone who's ever flinched at an unsubscribe notification.

EP 78: The unsubscribe paradox every marketer gets wrong

Here's what they cover:

- Why marketers are psychologically wired to fear unsubscribes

- The difference between list size as a vanity metric & list quality as a revenue driver

- What a healthy unsubscribe rate actually looks like in context

- When unsubscribes are a signal you're doing something right

- The three scenarios where an unsubscribe spike is a feature, not a bug

- Four metrics that matter more than your unsubscribe rate

- The benchmarks for when to celebrate, when to investigate, and when to panic

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

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

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

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

______

00:00 Welcome to the show

02:23 The unsubscribe paradox explained

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

08:32 The benchmarks for a healthy email program

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

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

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

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

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

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

21:39 The unsubscribe rate benchmark cheat sheet

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

25:48 Recap & final thoughts of the unsubscribe paradox

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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

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

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

Here's what we're diving into:

- What agencies are actually good at (and what they aren't)

- The revenue threshold for hiring in-house vs outsourcing

- Why strategy, customer insight, and brand voice should never leave the building

- The hybrid model that works: in-house owns strategy, agency owns execution

- When a project-based engagement beats a retainer

- The five red flags that mean it's time to fire your agency

- A four-question framework for making the call yourself

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

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

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

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

______

00:00 Welcome to the show

02:15 What agencies are actually good at (and where they fall short)

06:03 The case for hiring an agency

08:43 Using an agency for one-off projects

10:30 What you should never outsource

13:18 Protecting your brand voice

15:21 The hybrid model that actually works

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

23:44 The gatekeeping knowledge problem

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

27:09 Recap and final takeaways

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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!

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

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

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

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

Here's what they cover:

- Why creative velocity is now a competitive advantage in retention marketing

- The old workflow vs the AI workflow and where the time savings actually come from

- The four layers where AI helps most: ideation, copywriting, personalization, and iteration

- How to write a brief that gets AI to produce quality output instead of generic slop

- The five step workflow from brief to send

- The five point quality control checklist every AI draft should pass before it ships

- How to train AI on your brand voice using past emails and screenshots

- What AI still can't do: brand nuance, strategy, and deep customer insight

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

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

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

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

______

00:00 Welcome to the show

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

06:18 How AI compresses the creative timeline

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

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

19:00 Idea generation and picking the best campaign angles

22:07 Creating test variations from your edited base email

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

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

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

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

35:17 Recap of everything covered and final thoughts

______

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

______

Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

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!

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

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

EP 75: Creative testing that actually works in 2026

Here's what they cover:

-Why Apple MPP destroyed open rate as a reliable testing metric

-The single biggest testing mistake brands are still making in 2026

-The four layers of testing in order of impact; from positioning down to button colors

-Three approaches to testing when your list is too small for traditional A/B splits

-How to build a creative library that makes every future test smarter

-The learning velocity mindset that separates the best email teams from everyone else

-The HCE framework: hypothesis, control, evaluate

-How to know when you actually have a winner and when it's just noise

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

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

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

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

______

00:00 Welcome to the show

01:13 Why email testing got so much harder in 2026

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

05:20 The metrics you should actually be testing against

08:16 The one variable rule and why it matters

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

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

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

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

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

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

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

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

30:13 Recap of everything and final thoughts

______

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

______

Follow Jimmy & Chase on social!

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

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

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

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

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

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

EP 74: Conversion psychology: 6 principles for retention marketers

Here's what they cover:

• Why educational emails outperform promotional ones every time

• The urgency mistake that quietly trains your list to ignore you

• How to diagnose and remove the friction killing your conversions

• The subject line technique that makes people feel compelled to open

• Why the brands with the highest LTV sell identity, not just products

• How small actions like quizzes and reviews build toward a purchase

• A simple checklist to audit any email before you hit send

• A real replenishment email breakdown that hits five principles at once

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

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

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

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

______

00:00 Welcome to the show

02:30 Principle 1: Reciprocity - give value before you ask

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

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

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

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

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

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

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

30:43 Recap of all six principles and final thoughts

______

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

______

Follow Jimmy & Chase on social!

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

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

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

EP 73: Our 5 step ESP migration warmup guide

Here's what they cover:

The three reasons most ESP migrations fail before they start

Step 1: Setting up a fresh subdomain and authenticating SPF, DKIM, and DMARC

Step 2: Configuring platform settings before sending a single email

Step 3: Connecting your store and rebuilding your flows the right wayStep 4: The segmentation strategy that separates buyers from prospects and why it matters

Step 5: Monitoring reputation by TLD and what to do when things go wrong

When to hire help and what a managed migration actually costs

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

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

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

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

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00:00 Welcome to the show

02:44 Why most ESP migrations fail before they even start

05:55 Step 1: Setting up your new subdomain the right way

09:26 Step 2: Configuring your platform settings before you send anything

11:24 Step 3: Getting your store integration right

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

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

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

28:31 What to do when deliverability drops mid warmup

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

31:26 DIY migration vs working with a professional

33:40 Recap of all five steps and final thoughts

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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 & 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!