Good morning, Chase and Jimmy here.

Every brand says retention matters. Fewer actually sit down and look at what’s helping, what’s hurting, and what’s quietly getting ignored.

This morning, we’re sharing the exact framework we use to quickly review a brand’s retention engine. What’s firing, what’s missing, and what’s doing less than it should. You can run it in under an hour and it’ll give you a much clearer picture of where to focus next. So grab your coffee and lock in.

Also inside:
✔️ You can’t judge an email by its design... but Inboox can
✔️ Knowledge drop: Why selling right after checkout backfires
✔️ DTC wins: Popflex turns viral dupes into a sustainability play

Let’s get into it.

You can’t judge an email by its design... but Inboox can

Inboox’s AI Breakdown pulled apart Hello Bello's Valentine’s Day email and surfaced exactly why it performed:

• A bold, clear headline that instantly frames the offer

• Playful visuals that reinforce the brand voice

• A simple, direct CTA that drives action

It also flagged easy upgrades (stronger urgency and light personalization) that could push conversions even further.

That’s the power of Inboox.

Access over 1.5M Shopify emails and get instant AI insights, send time optimization, HTML and more.

→ Get started on Inboox.ai

A 60-minute retention diagnostic to find what’s actually holding growth back

You don’t need a replatform, a new ESP, or another tool to improve retention. Most brands already have enough data and infrastructure. What they’re missing is clarity.

This is a 60-minute retention diagnostic you can run a few times a year to understand what’s working, what’s leaking revenue, and where your effort will actually pay off. Think of it as a focused checkup, not a deep audit, designed to point you toward the highest-impact fixes.

1. Start with your data foundation

Before you look at campaigns or creative, make sure the data underneath everything is solid. If events are misfiring or attribution is messy, every insight downstream becomes unreliable.

Spend the first part of your diagnostic validating that your core events are syncing correctly between your ecommerce platform and your ESP.

What to check:

• View product, add to cart, checkout started, purchase, and subscription events

• Event duplication or missing events

• Consistent UTM naming conventions across campaigns

• Proper subdomain setup and authentication for email sending

If your data is fragmented, nothing else in this process will be trustworthy. Fix this first.

2. Check deliverability and list health before blaming performance

When emails underperform, creative often gets the blame. More often than not, the real issue is list quality.

Look at engagement over time, not just the last send. This helps you understand how quickly interest drops off and where fatigue starts to creep in.

Focus on:

• Engagement by 7-day, 30-day, and 90-day windows

• Bounce rates and spam complaints

• How long inactive subscribers remain on your list

If you’re still mailing people who haven’t engaged in six months, you’re hurting both performance and deliverability. List cleaning isn’t about shrinking your audience. It’s about protecting reach with the people who still care.

3. Map your lifecycle automation coverage

Next, step back and look at automation as a system, not a collection of individual flows.

Most brands cover the basics. High-performing brands make sure automation supports the full customer journey.

Ask yourself:

• Do we guide customers after the first purchase, not just before it?

• Are there replenishment or reorder nudges tied to actual product usage?

• Do we collect feedback at meaningful moments, not just right after delivery?

• Are VIPs treated differently, or just labeled differently?

Automation should reduce friction and decision-making for the customer. If it exists but doesn’t actively move someone forward, it’s probably underperforming.

4. Pressure test your segmentation strategy

If segmentation starts and ends with openers versus non-openers, you’re leaving money on the table.

Good segmentation changes the experience someone has with your emails. It makes messages feel timely without adding complexity.

Prioritize behavior-driven segments like:

• First-time buyers versus repeat buyers

• Category or product-line loyalists

• High AOV or high-frequency customers

• Seasonal or gift-driven purchasers

One simple rule that saves a lot of frustration: always exclude people who’ve already taken the action. Sending a promo to someone who already redeemed it erodes trust fast.

5. Evaluate creative for clarity, not cleverness

Creative does not need to be flashy to convert. It needs to be understood quickly.

Review your emails on mobile first and ask how fast someone can answer two questions: What is this about? What am I supposed to do next?

Things to look for:

• Clean headers that set context without distraction

• Short sections instead of long walls of text

• Clear visual hierarchy that naturally leads to the CTA

• Buttons that are easy to spot and tap on mobile

When design gets too busy, the message gets lost. When it’s clean and intentional, engagement often improves without changing a single word of copy.

6. Review offers through the lens of customer experience

Retention is not driven by discounts alone. It’s driven by how easy and rewarding it feels to keep buying from you.

Look at how you encourage second purchases and long-term engagement.

Evaluate:

• Whether cross-sells and upsells are relevant or random

• If loyalty rewards feel meaningful or forgettable

• How much education and guidance customers get after purchase

• How easy returns and support feel when something goes wrong

Strong offers work best when they feel like a continuation of the relationship, not a constant attempt to extract value.

7. Tie performance back to lifetime value

End the diagnostic by zooming out from individual sends and flows.

Look at:

• Repeat purchase rate by cohort

• Time to second purchase

• Customer lifetime value trends

• Where customers tend to drop off in their journey

This is where everything connects. The goal isn’t better open rates or higher clicks in isolation. It’s understanding which efforts actually move lifetime value and which ones just look good in reports.

Wrapping it up: Clarity beats complexity

This retention diagnostic isn’t about fixing everything at once. It’s about knowing where to focus.

When you understand where the biggest gaps are, you can stop guessing and actually start prioritizing. Run this quarterly, document what changes, and let it guide your roadmap instead of reacting to short-term metrics.

Knowledge drop:

Most brands try to sell more right after checkout. Jimmy explains why that’s a mistake, and how post-purchase emails should focus on reassurance before revenue.

DTC wins:

Instead of letting copies of her viral Pirouette Skort end up in a landfill, Popflex founder Cassey Ho launched the Popflex Upcycle Project. This new initiative turns dupe skorts into DIY fashion kits designed by independent creators. It’s a smart blend of IP protection, sustainability, and community-driven creativity.

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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