Good morning, Chase and Jimmy here!

Today’s a milestone for us at eCom Email Marketer: 100 editions.

If you’ve been here since the beginning last October, thank you for showing up every week. If you’re new, welcome aboard. Either way, our goal’s always been the same: share actionable strategies you can actually use to keep the revenue rolling in.

After 100 editions, one thing hasn’t changed: email and SMS retention isn’t complicated. But it does take work.

Between the two of us, we’ve spent 20+ years sending millions of emails, running thousands of campaigns, and helping brands generate hundreds of millions in revenue.

So to celebrate 100 editions, we’re sharing 10 of the biggest lessons each of us have learned along the way.

Also in the edition:
🎂 How one simple automation drove $37K in sales
>> The Year-Round Retention Playbook (Real tactics for slow months)
🗞️ Quick Clips: 4-day Prime Day, a Sauz-y deal, tips for Reel-ing in the views, and how Beckham scored a sweet new gig

👇 Let’s get into it.

🎂 One workflow. $37K in sales.

The Cake Store didn’t need 10 automations.

They needed one smart one.

The Cake Store was frustrated with Mailchimp’s limitations: no product imports, no flexible automations, and a clunky interface. So they switched to Omnisend and quickly built a custom reminder flow that sent customers a timely nudge just before their next big celebration. The result? A 32x higher conversion rate and over $37,000 in revenue>>from a single automation.

What made it work:

• A 340-day delay + past purchase trigger = birthday magic

• Omnisend’s Product Picker to drag products straight into emails

• A lean automation that upsold right on time

• Easier to set up (and support that actually helped)

🎊 Celebrating 100 Editions: 10 Things We’ve (Each) Learned About Retention Marketing

100 issues. 20+ years of experience. Millions of emails and texts sent. Hundreds of millions in revenue generated.

We’ve seen what works, what doesn’t, and what actually drives growth. The tactics evolve, but the fundamentals stay the same.

To mark 100 editions, we’re each sharing 10 of the biggest lessons we’ve learned helping brands grow through email and SMS.

No fluff. No theory. Just what works.

10 Lessons from Chase: What Actually Drives Retention

1️⃣ Treat Your Subs With Respect

Email isn’t a free billboard. It’s permission-based. Subscribers give you access to their inbox expecting value, not endless sales pitches. Brands that protect this trust win long-term attention and loyalty.

Key Takeaway: Before every send, ask: "Would I find this valuable if I were my customer?"

2️⃣ Reignite The Fire

When subscribers disengage, it's usually a relevance problem. Every unopened email signals misalignment between your offer and their needs. Change up your approach to re-engage them before they churn for good.

Key Takeaway: Use re-engagement campaigns with fresh offers or exclusive content to revive inactive subscribers.

3️⃣ Be Unexpected

Predictability kills engagement. Surprise, humor, or curiosity can disrupt patterns and draw people back in. Make your emails feel like messages your audience looks forward to opening.

Key Takeaway: Use curiosity-driven subject lines, pattern interrupts, and content that sparks a reaction to drive higher open rates.

4️⃣ Test Everything

Retention isn’t set-and-forget. Small iterative tests compound into significant gains over time. If you're not testing, you're guessing.

Key Takeaway: Always run A/B tests (subject lines, send times, offers) and track statistically significant lifts in open, click, and conversion rates.

5️⃣ Tag Everyone

Your subscribers are constantly telling you what they care about. Every click, product view, and purchase offers data you can act on. Proper tagging turns passive data into active targeting opportunities.

Key Takeaway: Tag behaviors like multiple purchases, SKU interest, AOV thresholds, and abandoned carts to drive smarter segmentation and retargeting.

6️⃣ Get To The Point

Inbox competition is brutal. You have seconds to grab attention, clarify value, and drive action. Fluffy intros lose readers fast.

Key Takeaway: Your subject line should earn the open, your headline should earn the scroll, and your CTA should earn the click. One message, one action.

7️⃣ It’s A Relationship

Email is permission-based marketing. Treat it like an ongoing relationship where you deliver value consistently, not just when you want to make a sale.

Key Takeaway: Balance your sends: mix educational content, product education, and soft sells to build long-term trust.

8️⃣ Be Useful

Every send should solve a problem, answer a question, or provide timely guidance. Utility keeps subscribers engaged and conditioned to open future messages.

Key Takeaway: Anchor every send in a customer problem or need. Utility drives engagement, which drives revenue.

9️⃣ Don’t Make Them Sick Of You

Frequency isn’t bad… irrelevance is. Find your cadence sweet spot based on your audience's tolerance and your content pipeline.

Key Takeaway: Monitor unsubscribes and spam complaints closely to calibrate ideal send frequency.

🔟 Quality > Quantity

A bloated list filled with disengaged subscribers tanks your deliverability and inflates costs. Focus on acquiring people who actually want to hear from you, and maintaining a list that performs.

Key Takeaway: Prioritize clean acquisition (zero pop-up tricks) and regular suppression of inactive profiles. A lean, engaged list drives better inboxing, higher CLTV, and stronger campaign results.

10 Lessons from Jimmy: The Stuff Brands Overcomplicate

1️⃣ Send More Than You Think

Most brands under-send out of fear. But consistent communication trains your audience to expect (and respond to) your messages. Inactivity breeds disengagement.

Key Takeaway: Build a weekly campaign cadence. Consistency builds trust and trains engagement behavior.

2️⃣ Campaigns Move the Needle

Automations are great, but they're not enough. Campaigns create urgency, excitement, and consistent reasons for people to come back.

Key Takeaway: Use campaigns to drive momentum between flows. Map out monthly campaigns tied to product drops, seasonal hooks, or education.

3️⃣ Retention Starts On Day 1

Retention isn't something that starts after the second order; it begins with how you onboard every customer. Their first post-purchase experience sets the tone for whether they'll buy again.

Key Takeaway: Optimize your post-purchase flow immediately: product education, cross-sells, referral asks, and usage tips drive early repeat purchases.

4️⃣ Data Without Action Is Useless

Collecting data doesn’t make you data-driven; acting on it does. Most brands track everything but rarely use it to inform strategy.

Key Takeaway: Focus on core metrics: revenue per order, lifetime value, repeat purchase %. Build flows that directly improve these numbers.

5️⃣ Make It Stupid Easy to Buy Again

Every extra step costs you sales. Once someone is ready to purchase again, your job is to make that as frictionless as possible.

Key Takeaway: Use personalized product recommendations, pre-filled carts, fast checkout, and clear CTAs to reduce friction.

6️⃣ Segmentation Is Overcomplicated

Most brands build overly complex segments that create more confusion than clarity. Simplicity scales better.

Key Takeaway: Build segments based on buying stages: first-time, repeat, VIP. Speak to the needs of each group differently.

7️⃣ No Such Thing As Set-And-Forget

Flows decay over time. What worked last year may be irrelevant today. Build a habit of continuous optimization.

Key Takeaway: Schedule quarterly flow audits. Review performance and refresh creative, offers, and logic based on new data.

8️⃣ Obsess Over Repeat Purchase %

Revenue is easy to chase. Repeat purchase % reflects the true health of your customer relationships.

Key Takeaway: Track repeat rates by cohort (30, 60, 90 days). Build incentives to drive faster second and third purchases.

9️⃣ Stop Copying The Big Brands

Enterprise brands play a different game: big budgets, broad brand awareness, and endless resources. Most DTC brands can’t afford to follow their playbook.

Key Takeaway: Focus on cash flow, LTV, and customer intimacy. Not splashy brand campaigns that don’t convert.

🔟 Retention Is The Long Game

Retention compounds slowly but meaningfully. Sustainable retention isn't built with hacks; it's built with consistency.

Key Takeaway: Set LTV growth goals over 6, 12, and 24 months. Play long-term games with long-term customers.

Here’s to the next 100.

If you’ve been reading this whole time, you’re already ahead of 90% of brands out there.

Let’s keep building.

📅 The Year-Round Retention Playbook

Most brands ghost their customers after Q4.

Big mistake. Your best chance to build loyalty (and drive repeat revenue) is during the quiet months... if you know how to use them.

That's why we put together The Year-Round Retention Playbook; a 7-part email series that breaks down how to turn slow months into strategic wins. No fluff, just real tactics you can plug into your calendar today.

Inside, you'll learn how to:

✅ Run urgency-driven flash sales that don’t feel spammy
✅ Tie campaigns to real customer goals, not just the calendar
✅ Make referrals, reviews, and loyalty perks work year-round
✅ Segment smarter to send more personalized, better-timed emails
✅ Track the right metrics to know what’s actually working

And it's free! Access the series now.

🗞️ Quick Clips

• Double Time Prime Time: Amazon’s turning up the heat with a 4-day Prime Day this year (July 8–11). Deals will drop every 5 minutes, with big brand promos and a LeBron-led ad campaign fueling the summer sales frenzy.

• A Sauz-y deal: Sauz just raised $12M to reinvent your pasta night. With 7,000+ stores already stocking their modern sauces, they’re betting bold flavors and better ingredients will win over the next generation of home cooks.

• Beckham Scores a Sweet New Gig: David Beckham is officially in the snack game. BEEUP, his honey-powered fruit snack brand, just hit Target shelves. Non-GMO, dye-free, and made for parents who want better-for-you options without the junk.

• LinkedIn Says: Hook ‘Em Early: LinkedIn’s new video tips are clear: don’t just upload; optimize. Start with a strong hook, add engaging captions, and focus on one clear message to drive views and engagement.

• Reeling in The Views: Instagram is testing “Trial Reels,” letting creators test content with non-followers first. Early results: 80% are seeing reach gains, helping creators double down on what actually works before going wide.

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

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