Send It!

Send It!

By Send It!BusinessMarketing
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Send It! episodes

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

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


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


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


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


    Here’s what they’re digging into:

    - Why discounts borrow from future revenue and make the problem worse

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

    - Framework 2: Bundling products to sell outcomes, not just SKUs

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

    - Framework 4: Content micro-wins that build confidence and drive repeat purchases

    - Framework 5: Winning on convenience and service instead of price

    - What a no-discount retention calendar actually looks like week to week

    - The mindset shift from promo calendar to lifecycle marketing


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


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


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


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


    ______


    00:00 The discount addiction nobody wants to talk about

    02:35 The discount death spiral explained

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

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

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

    17:56 The four step drop strategy broken down

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

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

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

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

    33:01 Recap of all five frameworks and final thoughts


    ______


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

    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    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!

    35 min
  • EP 71: The funniest things email marketers did in 2025

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


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


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


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


    Here's what we're getting into:

    • The top 10 most used emojis in subject lines (the number one will surprise you)
    • Which celebrities got name-dropped most - and why Drake topped the list
    • The TV shows and movies marketers referenced most
    • Why owls beat dogs and cats as the most mentioned animal
    • The internet culture moments brands actually leaned into
    • Most mentioned holidays and whether the order matches the revenue
    • The overused cliches showing up in thousands of campaigns
    • Why "exclusive" appeared in over 74,000 campaigns
    • The oops and apology email trend - and how much of it was intentional


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


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


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


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


    ______


    00:00 Welcome to The Show

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

    08:43 The TV shows and movies marketers referenced most

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

    15:54 Internet culture moments brands actually leaned into

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

    17:46 Viral moments that made it into email campaigns

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

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

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

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

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

    30:12 How 82% of marketers start their emails

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


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    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!

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

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


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


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


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


    Here's what we're diving into:


    -Why setting retention-specific goals changes everything (and why most brands skip this)

    - What "layer two metrics" actually means and why open rates aren't enough

    - How top brands look beyond email and SMS to drive retention across every channel

    - Using retention data to fuel acquisition and close the feedback loop

    - Why a strong product and honest internal feedback matter more than any campaign

    - How 8 and 9-figure brands rapidly test technology without getting distracted by the hype

    - The real role AI should play in a retention strategy (and what it can't replace)


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


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


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


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

    ______


    00:00 Welcome to The Show

    02:00 Meet Our Guest: Feras's Khouri

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

    10:00 #1: Set retention-specific goals

    14:00 #2: Understand layer two metrics

    17:00 #3: Look beyond email and SMS

    22:00 #4: Use retention for acquisition

    27:00 #5: Create an internal feedback loop

    37:00 #6: Rapidly test technology

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

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


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    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!

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

    AI is everywhere in email marketing… but is it actually working


    In this episode of Send It, Jimmy Kim sits down with Filip Pejic, Co-Founder of Bedford & Pearly, to talk about how smart email marketers are actually embracing AI right now (and where it's still falling flat). Plus, Filip shares three real campaign ideas that are driving serious clicks and engagement for brands today.


    From training entire agency teams on AI design tools, to why ChatGPT is making copywriters lazier, to the Super Bowl halftime sale that became a client's biggest revenue hour ever; this episode is full of honest takes and actionable ideas.


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


    Here's what we're diving into:

    - How Filip's agency runs weekly AI training sessions with their whole team

    - Why AI copywriting is creating a "degradation of ideas" + what to do instead

    - The flowchart email concept that's unlocking click engagement for brands

    - How a 60-minute Super Bowl halftime sale drove record-breaking revenue

    - The nostalgic Valentine's Day campaign that crushed for an apparel brand

    - Why timely, unexpected promotions beat perfectly scheduled campaigns

    - Jimmy and Filip's take on where email is headed as AI agents emerge


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


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


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


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


    ______


    00:00 Why Most Brands Are Using AI Wrong

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

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

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

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

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

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

    19:43 Using Gemini to Align Copy and Design Faster

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

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

    24:05 Why Retention Still Needs Humans

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

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

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

    37:16 Final Takeaways: What Actually Matters


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    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!

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

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


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


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


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


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


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


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


    Here's what we're diving into:

    - The modern customer journey most brands ignore after first purchase, and how to fix it

    - How segmentation should mature from basic to predictive

    - Strategy for making email and SMS work in tandem

    - How to leverage AI while maintaining the human touch to build trust

    - The 8 automations that form a real retention engine

    - The 2026 retention scorecard

    - A simple 90-day plan to implement the framework


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


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


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


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


    ______


    00:00 Welcome to The Show

    04:04 The Importance of Retention Marketing

    09:58 The Modern Customer Journey

    15:06 Effective Segmentation Strategies

    18:37 Channel Pairing: Email and SMS

    21:05 Leveraging AI in Retention Marketing

    25:11 Personalizing Messages at Scale

    26:52 Optimizing Key Flows for Retention

    28:35 Advanced Retention Strategies

    32:58 Metrics That Matter in 2026

    39:35 Implementing a 90-Day Retention Plan

    42:19 Final Thoughts and Resources


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    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!

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

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


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


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


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


    Here's what we're diving into:

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

    - How inbox providers now use engagement as a visibility signal

    - The 4-layer engagement stack top brands are adopting

    - Which metrics actually prove retention impact to leadership

    - How to rethink attribution without chasing “perfect” numbers

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


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


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


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


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


    ______


    00:00 Welcome to The Show

    02:21 Redefining Engagement Metrics

    02:54 Impact of Privacy and AI on Email Marketing

    04:37 New Requirements from Google and Yahoo

    05:43 Gmail's Algorithm and Engagement

    07:38 The Shift to Quality Over Quantity

    11:49 Building a Real Engagement Stack

    14:50 Key Email Metrics

    15:23 SMS Metrics Overview

    16:04 Customer Behavior Insights

    17:24 Business Outcomes Metrics

    20:05 Challenges in Attribution

    25:01 Actionable Steps for Improvement

    28:32 Conclusion and Wrap-Up


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    https://x.com/yojimmykim

    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!

    30 min
  • EP 66: 12 Unusual segments that drive serious eCommerce revenue

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


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


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


    EP 66: 12 Unusual segments that drive serious eCommerce revenue


    Here's what we're diving into:

    • How to identify discount rejectors, promo-only buyers, and risky first-time customers

    • What to actually send each segment (not just how to build them)

    • The 3 things every good segment should change in your marketing

    • How to avoid over-discounting and protect your brand's positioning


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


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


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


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


    ______


    00:00 Welcome to The Show

    04:29 Why Microsegmentation Matters for Your Business

    09:33 12 Unusual Segments for Revenue Growth

    09:46 Discount Rejectors

    11:25 Product Loyalists

    13:05 Risky First-Time Buyers

    15:09 High AOV, Low Frequency Buyers

    16:55 Engagement Only Buyers

    19:02 Seasonal Only Buyers

    21:58 Promo Only Buyers

    23:43 Reactivating Recently Lapsed High-Value Buyers

    25:26 Engaging Multi-Category Explorers

    26:56 Converting Subscription-Adjacent Buyers

    29:28 Recognizing and Rewarding Brand Advocates

    33:39 Understanding and Targeting Silent VIPs

    35:37 Tips for Implementing Segmentation Strategies

    40:27 Recap and Final Thoughts


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    https://x.com/yojimmykim

    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!

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

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


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


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


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


    Here's what we're diving into:

    - The 4 critical stages in a subscriber’s first 45 days

    - How to create emotional “micro-wins” that build brand trust

    - Using habit loops to make your product part of the customer’s routine

    - The importance of timing in repeat purchase messaging

    - Real brand examples and lifecycle strategy breakdowns


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


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


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


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


    ______


    00:00 Welcome to The Show

    03:02 The Critical First 45 Days of a Subscriber's Life

    08:08 Breaking Down the First 45 Days into Stages

    16:00 Creating Micro Moments and Micro Wins

    20:27 Understanding Habit Loops: Cue, Routine, Reward

    23:00 Building Habits Through Email and SMS

    26:37 The Importance of Repeat Trigger Windows

    29:26 Proactive vs. Reactive Messaging

    31:51 Calculating and Utilizing Repeat Trigger Windows

    34:05 Bringing It All Together: A Cohesive Strategy

    36:28 Conclusion and Recap


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    https://x.com/yojimmykim

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

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

    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!

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

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


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


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


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


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


    Here's what we're diving into:

    - Why your campaign-heavy strategy is missing out on potential gains

    - The underrated flow that beats abandoned cart in both revenue and conversions

    - How to turn transactional emails like shipping updates into revenue-generating touchpoints

    - When SMS actually converts (and when it’s just wasting your send)

    - The 5 automations you should prioritize


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


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


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


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


    ______


    00:00 Welcome to The Show

    02:17 Key Insights from the Report

    07:54 Transactional Emails: Untapped Potential

    12:24 Preparing for Q4: Strategies and Insights

    16:44 The Role of SMS in Marketing

    17:57 SMS Campaigns vs. Automations

    21:31 Optimizing SMS for eCom

    24:34 Order Growth Insights

    26:22 Global eCom Trends

    27:30 Fundamentals of Automation

    35:35 Campaigns vs. Automations

    39:22 Final Takeaways and Recommendations


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    https://x.com/yojimmykim

    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!

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

    Struggling with retention but not sure what’s broken?


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


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


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


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


    Here's what we're diving into:

    - The 7-part retention audit framework

    - What to check when open rates drop

    - How to evaluate deliverability, infrastructure, and attribution

    - Which flows every DTC brand should have (and most don’t)

    - High-impact segmentation strategies

    - The biggest mistakes brands make in messaging, offers, and timing


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


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


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


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


    ______


    00:00 Welcome to The Show

    03:12 Retention Audit Framework Overview

    04:17 Data Infrastructure: The Foundation

    08:51 Deliverability and List Quality

    15:37 Lifecycle Automation: Maximizing Revenue

    20:17 The Importance of Timely Replenishment

    23:09 Effective Segmentation Strategies

    26:43 Crafting Mobile-Optimized Emails

    31:08 Enhancing Customer Experience Beyond Emails

    35:47 Analyzing Metrics for Better Retention

    37:56 Final Thoughts and Recap


    ______


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


    ______


    Follow Jimmy & Chase on social!


    Follow Jimmy Kim at:

    https://x.com/yojimmykim

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

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

    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!

    40 min

About Send It!

From the publisher's feed

The SendIt Podcast, hosted by email marketing experts and veterans Jimmy Kim and Chase Dimond, is your go-to for leveling up your retention game. Jimmy, Founder and mastermind behind Sendlane, brings…