A funny thing happens when brands discover SMS works.

The first few campaigns perform well, revenue starts rolling in, and suddenly every promotion becomes a text message.

Then the opt-outs show up.

SMS is one of the most effective channels in retention marketing, but it's also one of the easiest channels to burn out.

This week, we're breaking down what actually makes SMS work, how to write messages people want to receive, and the mistakes that quietly kill performance.

Also inside:

→ People trust strangers on the internet more than brands.
→ Knowledge drop: The 3-second checkout moment that quietly creates buyer's remorse
→ Retention breaks when every channel operates like it's an only child.
→ Diamond Brew sells out 3x after 7-figure pre-seed + REMEDY lands Series A

People trust strangers on the internet more than brands.

Think about it… before buying, we check reviews, ask friends, search Reddit, etc. 

We'll take advice from someone with a cartoon profile picture before we believe what's written on a product page.

Why?

Because it feels human.

And let’s face it, most retention marketing… doesn't.

It's emails. Texts. Notifications. Messages talking at people.

Outcraft reaches them while the purchase is still sitting in their head.

→ Calls abandoned checkouts within minutes
→ Follows up across SMS, email, and WhatsApp with the context from the conversation
→ Even collects payment over the phone

Turns out people still like talking to people (even when one of them isn't human).

See what recovered revenue sounds like → outcraft.ai

*Sponsored

Knowledge drop

Most brands obsess over getting the sale. Jimmy highlights the tiny moment that happens after the click; and why filling the "confirmation gap" with reassurance instead of silence can reduce doubt before it turns into regret.

The SMS Playbook: How to make 160 characters actually matter

SMS can drive outsized results for retention teams, but it leaves very little room for error.

What makes the channel so powerful is also what makes it easy to get wrong.

The brands that consistently win with SMS understand that success doesn't come from sending more messages. It comes from sending messages that are timely, relevant, and worth the interruption.

Every text has to earn its place.

Let’s dig in.

1. Respect what makes SMS different

Email gives you room to educate, tell stories, explain offers, and build context. SMS gives you a much smaller window to create action. That means every decision becomes more important, from the first few words to the timing of the send.

Three realities shape every successful SMS program:

• It interrupts. A text arrives immediately and demands attention in a way email rarely does.

• It's constrained. Character limits force clarity. There isn't room for fluff, lengthy explanations, or multiple competing messages.

• It carries a higher expectation of relevance. Customers are far less forgiving of unnecessary texts than unnecessary emails.

Strong SMS strategy starts with understanding those constraints and building around them instead of fighting against them.

2. Build every SMS around a simple framework

A surprising number of SMS messages fail because they straight up just try to do too much.

The best-performing texts are usually built around three simple components:

• A hook that earns attention

• A clear value proposition

• One obvious action

The hook is what gets the message read, the value gives the reader a reason to care, and the action removes any ambiguity about what to do next.

For example:

Last chance: your cart is about to expire. Complete your order in the next hour and save 15% → [link]

The message works because it quickly answers three questions:

• Why am I receiving this?

• What's in it for me?

• What should I do next?

Whenever one of those answers is missing, performance tends to suffer.

3. Match the timing to the intent

Great SMS performance often has less to do with copy than marketers think.

Timing does a lot of the heavy lifting.

A cart abandonment text works because intent is still fresh. A replenishment reminder works because it arrives close to the moment someone needs more product. A launch alert works because exclusivity has a shelf life.

Different message types deserve different timing strategies:

Before writing the message, make sure you've identified the right moment for it to arrive.

The best copy in the world can't fully compensate for bad timing.

4. Personalize beyond the first name

Most personalization starts and ends with a merge tag.

That's rarely enough anymore.

Customers feel understood when the message reflects something they actually did.

Some of the strongest personalization opportunities come from:

• Products previously purchased

• Browsing behavior

• Loyalty status

• Purchase frequency

• Geographic relevance

A replenishment reminder that references the exact product someone purchased feels far more useful than a generic promotional text. The same goes for VIP launches, regional promotions, and behavior-based recommendations.

The goal isn't personalization for personalization's sake. The goal is relevance.

5. Test the details that influence behavior

SMS optimization tends to happen in small increments.

Tiny changes can have an outsized impact because there isn't much competing for attention inside a text.

Areas worth testing include:

At the same time, pay close attention to opt-out behavior.

Opt-outs are one of the most honest forms of customer feedback available. If unsubscribe rates spike after a campaign, the issue is usually larger than the copy itself. It could be frequency, targeting, timing, or a mismatch between the offer and the audience.

The channel will tell you when something isn't working... but YOU have to pay attention.

6. Let AI handle variation, not strategy

AI can be extremely useful for SMS because the format is so constrained.

One of the biggest challenges with SMS is generating enough high-quality variations to test. And that's exactly where AI can save time.

Use it to:

• Generate multiple hooks for the same offer

• Explore different psychological angles

• Shorten longer drafts

• Create testing variations

Now, what it shouldn't replace is strategic judgment.

AI doesn't know your customer as well as you do. It doesn't understand the nuances of your brand voice or your audience's buying behavior.

Use AI to accelerate execution while keeping strategy firmly in human hands. A strong prompt can produce five solid variations in seconds, but choosing the right one is still your job.

Better SMS starts with respecting the channel

SMS rewards discipline more than almost any other marketing channel.

The brands that perform best are choosing relevance over frequency. They're timing messages better. They're segmenting more thoughtfully. And they're treating every message like it has to earn its place on the lock screen.

Because it does.

When every text delivers a clear value exchange, customers stay subscribed longer, engagement stays healthy, and SMS becomes one of the most profitable channels in your retention mix.

Retention breaks when every channel operates like it's an only child.

Email does one thing. SMS does another. Paid traffic lives in its own world.

EditStudio took the opposite approach for fashion retailer White Mood, connecting acquisition, retention, and customer behavior into one coordinated system (all inside Omnisend).

The result?

→ €1.3M from cart recovery
→ €477K from a welcome flow
→ 44%+ open rates across key automations

Turns out customers convert better when your marketing remembers what they've already done.

👉 See how EditStudio built it

*Sponsored

DTC wins:

Diamond Brew Sells Out Three Times After Seven-Figure Pre-Seed

Coffee startup Diamond Brew closed a seven-figure pre-seed and has already sold out three times across TikTok Shop and Amazon. Founder Douglas Yu spent 2,000+ hours on TikTok Live building the brand's audience, proving that consistency and community can be just as powerful as paid media.

REMEDY Lands Series A Led by L Catterton

Dermatologist-developed skincare brand REMEDY raised a Series A led by L Catterton, with participation from Norwest and Sonoma Brands Capital. The funding will support clinical research, new product development, and expansion across DTC, Amazon, and Target as the brand continues its rapid growth.

Annnnd that’s a wrap for this edition! 

Thanks for hanging with Chase and me, always a pleasure to have you here.

If you found this newsletter helpful (or even just a little fun), don’t keep it to yourself! Share ecomemailmarketer.com with your favorite DTC marketer. Let’s get them on board so they don’t miss next week’s drops.

Remember: Do shit you love.

🤘 Jimmy Kim & Chase Dimond

PS - Your next best customer might be reading this right now. Want in? Email Jimmy to sponsor this newsletter and more.

Love this newsletter but want to receive it less frequently? Let us know by clicking here!