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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. I...

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 attribut...

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 workin...

The email "best practices" everyone repeats are quietly costing your brand real money. In this episode, Jimmy Kim and Chase Dimond break down 10 hot takes on retention marketing that go against almost everything you've been told. From welcome series aggression to subject line strategy to why unsubscribes can actually be a good sign, they back every take with data and real-world exper...

The 5-person retention team is on borrowed time. In this episode of Send It, Jimmy Kim and Chase Dimond go on the record about something a lot of brands have been quietly doing for the last 12 months. The traditional retention pod (manager, two coordinators, designer, copywriter, SMS specialist) is getting restructured out of existence. CFOs are running the math, AI got actually good, and the tool...

Letting AI hit send on your email program is how brands lose their list overnight. In this episode of Send It, Jimmy Kim and Chase Dimond join Bernard Meyer, Omnisend's AI Operations Manager, to get on the record about what AI in email marketing actually looks like when it's working and where the fully autonomous fantasy falls apart. Brand voice drift, deliverability damage, and irreversib...

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...

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...

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 o...

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 t...

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 sig...

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...

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...

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 deci...

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 wh...

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, thi...

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...

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 do...

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 bra...

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 tr...

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 g...

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...

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...

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...

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...