Hey, it's Chase and Jimmy here.

Retention marketing in 2026 isn’t about doing more. It’s about knowing where the line is and not crossing it, especially now that customers are smarter, more aware, and quicker to tune brands out.

This morning, we're breaking down how to stay proactive without becoming pushy, where brands still get themselves into trouble, and how to build a retention program that actually holds up long term.

Also inside:

✔️ Email changed a lot in 2025. Most brands just haven’t caught up yet.
✔️ Your inspo folder is just vibes. This is data.
✔️ Quick clips: This week's top eCom news stories

Let’s dive in.

Email changed a lot in 2025. Most brands just haven’t caught up yet.

Omnisend’s 2025 Email Report breaks down the benchmarks, performance shifts, and patterns that actually mattered this year (and what they signal for 2026). In this live session, the team walks through what moved, why it moved, and how brands should adjust as they get their new year strategies locked in.

If you’re planning budgets, flows, or KPIs for 2026, this is the data you want in your corner.

January 29th @ 7:00 AM PT >> Register free

The line you shouldn’t cross: Smarter retention marketing in 2026

Retention marketing in 2026 is less about what you can do, and more about what you should do.

In 2026, brands have more data, more channels, and more automation than ever. That’s the upside. The downside is that it’s incredibly easy to overdo it. Send too much. Say too much. Get too clever. Cross a line without realizing it.

Ethical retention marketing isn’t about playing defense or just checking compliance boxes. It’s about knowing where the line is and choosing not to cross it, even when short-term gains are tempting.

The brands that last are the ones that respect the inbox, the phone, and the customer on the other side of the screen.

Here’s how that actually shows up in practice.

Why ethics matter more now than they used to

Customers aren’t naïve anymore. They know how marketing works. They know you track behavior. They know personalization exists.

What they’re paying attention to now is how you use that power.

Trust is fragile. One misleading subject line, one overly aggressive SMS streak, or one creepy reference to behavior can undo months of good will. And in a world where unsubscribing is easy and switching brands is easier, people won’t hesitate.

Ethical retention marketing does three important things:

• It keeps your brand credible

• It protects deliverability and engagement over time

• It builds relationships that actually compound

This isn’t about being “nice.” It’s about being sustainable.

The real balancing act: being proactive without becoming pushy

Every retention team is navigating the same tension. You want to stay visible, drive repeat purchases, and maximize LTV. But you also don’t want to crowd the inbox, overwhelm the phone, or turn helpful reminders into background noise.

The difference between proactive and pushy usually comes down to a few strategic choices.

1. Frequency should respond to behavior, not calendars

If your send schedule is driven by “we email X times per week,” you’re already behind.

In 2026, frequency works best when it flexes based on engagement. Recent buyers, active browsers, and high-intent segments can handle more touchpoints. Quiet subscribers can’t.

A smarter approach:

• Increase frequency when intent is clear

• Pull back when engagement drops

• Let behavior determine cadence, not internal schedules
  

Consistency matters, but relevance matters more. Silence is rarely the problem. Irrelevance is.

2. Personalization should guide decisions, not show off data

Just because you can reference a specific action doesn’t mean you should.

Good personalization helps customers move forward. Bad personalization reminds them they’re being tracked.

Use data to:

• Recommend products that make sense in context

• Anticipate needs based on past behavior

• Remove friction from repeat purchases

Avoid personalization that feels unnecessary or overly precise. If a message would make you pause as a customer, that’s usually your signal to simplify it.

3. Every message needs a clear reason to exist

One of the fastest ways to cross into “pushy” territory is sending messages without a clear purpose.

Before hitting send, ask:

• What’s the value for the customer right now?

• Why is this message better today than later?

• Who actually needs to see this?

If the answer is vague, the send probably is too. Strong retention programs prioritize intent over output.

Where brands still get themselves into trouble (and how to fix it)

Even well-intentioned teams fall into habits that quietly erode trust. The good news is most of these are easy to correct once you see them clearly.

Misleading subject lines

“Re:” and “Fwd:” tricks might spike opens once. Then they cost you credibility.

Clear, honest subject lines win long-term. Curiosity is fine. Deception isn’t.

How to fix it: Use curiosity without deception. Set clear expectations so the open feels rewarded, not tricked.

Shady sender names

If customers can’t immediately tell who the email is from, that’s a problem.

Consistency builds recognition. Recognition builds trust. Don’t hide behind clever aliases.

How to fix it: Stick to consistent, recognizable sender names. Familiarity builds confidence and improves engagement over time.

Making unsubscribing difficult

This one is simple. If someone wants out, let them out.

Easy unsubscribes improve list health, protect deliverability, and signal respect. Trapping people on your list only hurts you in the long run.

How to fix it: Make unsubscribing easy and visible. Pair it with preference options so customers can opt down instead of opting out completely.

Treating compliance as an afterthought

Regulations aren’t going away, and neither are customer expectations around consent.

How to fix it: Build compliance into your workflows early. Clear opt-ins, transparent messaging, and clean data practices protect both your brand and your performance.

What ethical retention looks like in practice

The brands getting this right aren’t perfect. They’re intentional.

They focus on:

• Clear communication about what subscribers can expect

• Preference centers that actually work

• Regular list cleanups

• Segmentation based on consented data

• Staying current on regulations without letting compliance drive creativity

Ethics isn’t a separate initiative. It’s baked into how decisions get made.

A better way to think about ethical retention

Ethical retention marketing isn’t about being cautious. It’s about being confident enough to play the long (smart) game.

It’s choosing long-term trust over short-term spikes.
It’s using data to help, not pressure.
It’s knowing when to show up and when to step back.

What you need is trust, consistency, and messages that feel worth receiving.

Because in 2026, the real competitive edge isn’t better automation.

It’s better judgment.

Your inspo folder is just vibes. This is data.

Be honest… how many “inspo” folders do you have right now that you totallyyy plan to revisit someday?

Exactly.

Inboox.ai fixes that.

It’s a searchable database of 1M+ real Shopify brand emails (flows, campaigns, promos, launches) the stuff brands are actually sending (and making money with). You can filter by brand, vertical, email type, and more, so instead of guessing what “good” looks like, you can literally see it.

Less staring at a blank doc.

More “oh… that’s what we should be sending.”

👉 Get inside Inboox.ai and get the competitive advantage

Quick Clips:

• Mid-Day Squares launches No Bread PB&J: The functional snack brand is ditching chocolate for the first time with a crustless PB&J-style bar. Now at select Target stores and online.

• David Protein goes bronze: The new dessert-style Bronze line combines candy bar texture with functional macros: 150 cals per bar, high protein, and flavors like S’mores Chocolate Crunch and Cookie Dough Caramel.

• Pat McGrath Labs heads to auction: The cult beauty brand known for pigment-packed formulas and collabs with Prada, Versace, and more is seeking a buyer. Bids are due Jan 26, with the auction set for Jan 27.

• How holiday 2025 played out: AI, tariffs & cautious shoppers: Inflation-weary consumers still showed up to spend; leaning on buy-now-pay-later, AI gift-finders, and early promos. Retailers leaned on nostalgia, exclusives, and tech to keep the season merry.

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.

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