A few weeks ago we were auditing a brand’s account and noticed something wild.

Thousands of people were clicking the same products, browsing the same collections, adding to cart… then disappearing.

And the brand’s response?

The EXACT same generic campaign everyone else got.

No follow up based on what people actually showed interest in. No triggered experience. Nada.

That’s the gap.

Your customers are constantly telling you what they want through their behavior. Most brands just aren’t listening.

So today, we’re breaking down how to use behavioral signals to build email and SMS flows that feel more relevant and convert way better.

Also inside:
✔️ Claude can now audit your campaigns
✔️ What happens when retention marketers leave their desks for a few days
✔️ Quick clips: the biggest eCom stories this week

Let’s get into it!

Your AI writes emails. It just can't send them… until now.

Your AI writes emails. Cool. So does everyone else’s. 😉

On May 20, Chase and I are joining Omnisend’s Bernard Meyer live to show you how we’re actually using Claude and ChatGPT to run an email program, not just write for one.

Here’s what we’re walking through live:
• Build and launch a full campaign from a single prompt
• Create segments using plain English instead of logic builders
• The reports AI is actually useful for (and the ones it completely screws up)
• Where we still step in manually and why
• Live Q&A + the exact prompts we use ourselves

The marketers who learn this stuff now are going to move way faster than the ones still doing everything manually six months from now.

Register now before you’re playing catch up later!

→ Register free

*Sponsored

The contextual data plays running 2026's highest-converting email programs

Marketing budgets are tighter, third-party cookies are gone, and your customers are smarter about ignoring generic email. The brands pulling outsized results from email and SMS in 2026 have one thing in common: they treat every click, view, and purchase as a signal, and they let AI route the response.

That's contextual data. And when used right, it's the difference between a campaign that converts at 1 percent and one that converts at 8.

Here's how to put it to work.

Decode the signals your customers are already sending

Contextual data, (AKA intent data), is the running record of what each subscriber actually does:

• Emails opened, clicked, or ignored

• SMS engagement and reply behavior

• Pages and products browsed

• Items added to cart, then abandoned

• Past purchases and reorder patterns

• Reviews left, support questions asked

Every one of those is a vote about what your customer wants next. Tag them and route them with AI, and they become the most accurate prediction of next purchase you'll ever get.

Example: A subscriber clicks an email link on earrings, browses three product pages, and bounces. That's a full intent statement, three signals deep. The right next message names the earring they almost bought and pairs it with the matching necklace.

Tag behavior automatically (and let AI fill in the gaps)

Manual personalization breaks the moment your list passes 5,000 subscribers. Lucky for you, behavioral tagging fixes that.

Here’s the basic version: when someone clicks an "earrings" link, your ESP auto-applies an "earrings-interested" tag. Every flow can branch off that tag.

The 2026 version layers AI on top:

• Intent classification. AI models read browse and click patterns and apply tags you didn't manually define. Omnisend AI segments and Klaviyo predictive analytics all do this.

• Predicted next purchase. Algorithms score each subscriber for what they're likely to buy next, based on look-alike behavior across your list.

• Churn risk flags. Subscribers drifting toward inactive get tagged before they unsub, so you can intervene with the right offer.

• Generative product recs. AI assembles a per-subscriber product block at send time, using their browse and purchase history.

Trigger smart flows from every signal

Tags are great, but useless without flows attached to them. These are the four highest-leverage triggers to build first:

1. Browse abandonment with category context. Subscriber views 2+ pages in a category within 10 minutes? Trigger a category-specific email, then an SMS 24 hours later if no engagement.

2. Cart abandonment with offer logic. First-time visitor abandoning gets education and social proof. Repeat customer abandoning gets a smaller, sharper nudge. AI picks the offer tier automatically.

3. Post-purchase cross-sell. Bought earrings? Three days later, send the matching necklace with a bundle discount. Bought a serum? Replenishment reminder hits at day 45.

4. Win-back triggered by absence. Subscriber goes quiet for 60 days? AI predicts which offer pulls their segment back, and the flow fires automatically.

Each of these gets built once and runs on autopilot. The compounding revenue from doing all four well usually beats every campaign you ship next quarter.

Pair email and SMS so the message lands twice

Email and SMS work harder together than apart. Every contextual flow should run across both in coordinated sequence.

Here’s how to layer them:

• Lead with email when there's content to read or browse: launches, drops, education

• Follow up with SMS when timing matters: cart, restock, flash sale, low stock

• Use SMS for shipping and confirmation, let email carry brand storytelling

• Stagger by 12 to 24 hours so the second touch lands when the first gets ignored

A subscriber offline still sees an SMS. A subscriber too busy at 9 AM might catch the email at 9 PM. Two channels means two real chances for the same message to convert.

Layer AI on top to scale personalization

The hardest part of contextual marketing used to be writing 50 versions of the same email. AI removed that bottleneck.

Three places AI is doing the heavy lifting now:

• Subject lines and preview text

• Dynamic email body content

• Send-time optimization

What to skip: don't let AI auto-write full campaigns yet. Use it for variants, dynamic blocks, and send timing. Voice and brand still need your human pass.

Run these three plays first

Contextual data only pays off when it's connected, tagged, and triggered. Three moves that pay back the fastest:

1. Audit your integrations today. ESP, SMS, Shopify, reviews. If any aren't syncing, fix that first.

2. Build behavioral tags for your top three product categories and turn on basic intent flows.

3. Switch on AI send-time and predictive segmentation in your ESP. Both are free in most platforms and lift results without a content lift.

Every email, click, and cart event your customers leave behind is a vote about what they want next. Tag the votes, route them with AI, and your marketing starts running smarter every week.

That's how clicks become customers.

What happens when a room full of retention marketers actually step away from their desks?

The retention marketers who level up this year are the ones getting in rooms like this.

Not watching recaps three weeks later. Not bookmarking strategies they never implement.

The Retention Roadshow is a one day deep dive into the email, SMS, and lifecycle strategies brands are using right now to drive more revenue in 2026.

• Tactical retention sessions
• Live workshops you apply in real time
• Direct access to operators scaling top brands
• 75–100 marketers per city max

Join us in a city near you this June!

NYC (6/5) 🍎 • Miami (6/8) ☀️ • LA (6/10) 🌴 • Austin (6/12) 🤠

Some cities are already close to selling out.

→ Use code ROADSHOW20 for 20% off before tickets are gone

Quick Clips: Tariffs, Prime Day & $38B Moms

• Tariff refunds are finally moving: US Customs just launched the CAPE system to start processing refunds on the IEEPA tariffs the Supreme Court struck down in February, which means hundreds of thousands of importers can finally get back a piece of the $160B+ that was paid. Refunds run on a 60-90 day timeline post-approval. If you imported anything during the IEEPA window, get your filings in.

• Prime Day moves to June: Amazon Prime Day 2026 is rolling out across 26 countries this June, with Australia, Brazil, India, and Japan joining later in the summer. Last year drove 13 billion+ same-day or next-day deliveries and a record number of independent sellers crossed $1M in annual sales.

• Mother's Day spend hits $38B: Consumers are budgeting a record $284.25 per person for Mother's Day 2026, with men planning to spend $346 vs women's $225. Experiences are gaining ground with Millennials and Gen Z, and the "gripe but swipe" mindset is real: shoppers complain about budgets and keep buying anyway.

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!