5 Stupidly Simple Retention Wins You’re Probably Ignoring

Hi Friends!

This newsie comes to you from the Offaimme Café at  The George, a relatively new hotel in the center of Tel Aviv, one of the greatest cities in the world.

It’s been a quick but packed work trip. I landed on Sunday, had a few full days, and am heading back home later tonight on the redeye. 

Last week, we went deep on the million-dollar question: how do you get more customers from orders #1 to #2? If you missed it, TL;DR: Most brands focus on the wrong things, and the smarter play is often doubling down on existing high-LTV customers instead of forcing unnatural behavior shifts.

But this week, I want to go even simpler.

For all the big, splashy retention strategies floating around—loyalty programs, fancy segmentation, SMS gamification—most brands miss the basic, lower-effort wins that could instantly improve retention.

Funny enough, I’ve seen 8- and 9-figure brands missing these same things.

Let’s fix that—fast

This week’s newsie is brought to you by Monocle, the AI-powered platform that allows you to create personalized offers to drive incremental revenue.

For too long, brands have been stuck using one-size-fits-all discounting strategies, leaving revenue on the table. Monocle changes the game, delivering personalized offers by understanding each customer’s behavior and purchase intent.

I met the founders a while back and was WOWED by what they are building. 

Brands like Honeylove, True Classic, Death Wish Coffee, and Obvi are already seeing the impact:

• 30% increase in revenue from email and sms flows by using smart offers

• 20% increase in popup signup rates from offer and timing optimization

• $1B total incremental revenue generated by Monocle to date

“Monocle has been invaluable in helping us deliver a shopping experience that captivates and converts without sacrificing profitability."

Kelly Spencer, Communications Marketing Manager at Death Wish Coffee

Here’s how it works: Monocle’s platform analyzes millions of customer signals before delivering the right offer to the right person at the right time. Whether it’s personalized email, SMS, or popups, Monocle’s AI ensures every incentive maximizes revenue and builds long-term loyalty.

Ready to stop guessing and start growing?

5 Quick Retention Wins Most Brands Ignore

Most brands chase larger, more significant, and flashier retention plays—membership programs, deep segmentation, gamified SMS—while skipping over the easiest high-impact wins.

I’ve seen 8- and 9-figure brands miss these five things. 

1. Build the Flows, Don’t Just Send Campaigns

A surprising number of brands don’t have core email flows set up. Even some pulling in $50M+ are missing the basics.

This usually happens when brands bring on an agency early. Since most agencies charge per campaign, the focus shifts to knocking out a few email sends a week instead of setting up automated flows that drive retention long-term while you are asleep.

Campaigns are great, but flows are what guide customers through their journey. They reinforce value, smooth out friction, and make repurchasing the obvious next step. If these aren’t dialed in, you’re making customers do too much work to stay engaged.

If you do nothing else, these three flows should be dialed in:

• Post-Purchase Flow
  Most brands underthink this. A strong post-purchase flow does three things:

  • Re-sells the product to reinforce the buying decision and eliminate buyer’s remorse.

  • Guides customers on how to maximize value—when to use it, how to get the best results.

  • Teases the next order by introducing refills, add-ons, or complementary products.

• Browse Abandonment Flow
  A well-timed reminder can recover a meaningful percentage of high-intent shoppers.

  • Remind them what they looked at—straight to the point.

  • Layer in social proof: reviews, best-seller status, or a quick customer quote.

  • Test a plain-text email here—sometimes, it outperforms polished, design-heavy emails.

• Winback Flow
  Some customers won’t come back unless you remind them. With minimal effort, a well-timed winback flow can recover 10-15% of lapsed customers.

  • Send before they fully ghost—timing matters.

  • Make reordering frictionless: subscription nudge, bundle deal, or a quick reorder link.

  • Skip the “we miss you” fluff—just deliver value.

2. Stop Sleeping on Plain-Text Emails

Most ecomm brands lean on polished, editorial-style emails. They look great—but they also blend into your inbox and often feel very promo-ey.

Plain-text emails can break through the noise.

• They feel personal—like a direct note instead of a mass email.

• They stand out—especially when everything else is over-designed.

• They drive replies—which leads to better engagement and trust.

I've seen brands double email engagement just by swapping a few campaign sends to plain text, especially for retention-focused emails.

3. Your Discount Strategy Is Costing You More Than You Think

Most brands treat discounts like a sledgehammer—big, broad, and imprecise.

“20% off sitewide.”
“$10 off your next purchase.”
“BOGO this weekend only.”

And look, these work to an extent. But when you’re blasting the same discount to everyone, you leave money on the table.

You are much better off providing personalized offers based on customer behavior.

Think about it—why would you give the same 20% discount to:

• Someone who just purchased it at full price last week?

• A VIP customer who already buys every month?

• A first-time shopper who might have converted anyway?

Instead, test smarter discounting strategies:

• Offer higher-value discounts to first-time buyers who hesitate at checkout.

• Give loyal customers early access to sales instead of straight-up discounts.

• Test low-risk perks like free shipping or bonus gifts before slashing prices.

This is exactly what Monocle (this week’s sponsor) helps brands do at scale. By analyzing millions of customer signals, it delivers the right offer to the right person at the right time, maximizing revenue without eroding margins.

4. Most Brands Ignore Low-Hanging Cross-Sell Revenue

Cross-sells are the easiest way to drive incremental revenue, yet so many brands completely ignore them.

The best time to sell someone more is:

• When they just bought something and are still excited about the brand. (very brand/product dependent–test it) 

• When they’re actively shopping and open to suggestions.

And yet, I can’t tell you how many brands just let customers check out and disappear without offering their customers a thoughtful and intentional cross-sell opportunity.

Easy fixes:

• Post-purchase upsells: Right after checkout, suggest an easy add-on. “Hey, you’ll love this with your order—add it now and get free shipping.” You can use tools like Rebuy, Zipify, Aftersell, etc. You can also easily add AI recommendations to your post-purchase emails with Yotpo email. 

• In-cart cross-sells: Tools like PrettyDamnQuick make recommending complementary products at checkout effortless.

• Smart reorder reminders: Instead of generic “time to restock” emails, personalize based on purchase history.

This isn’t complicated—it’s just about making the next purchase feel obvious.

5. Your Best Customers Are Getting Zero Recognition

This one baffles me.

Your best customers—the ones who spend the most, refer friends, and keep your business alive—get the same experience as a random first-time buyer.

A little recognition goes a long way:

• Send personalized thank-you emails to high-value customers. It doesn’t have to be fancy—just something real.

• Give top spenders early access to new drops or exclusive perks.

• Surprise VIPs with an occasional small freebie (without making it a formal program).

Brands obsess over acquisition while completely neglecting retention. Your highest-LTV customers are the easiest to keep happy, yet most brands do nothing to make them feel special.

And that’s an expensive mistake.

TLDR:

Most brands chase complicated retention plays while ignoring the stupidly simple wins:
✅ Set up three core email flows (post-purchase, browse abandonment, winback).
✅ Test plain-text emails to stand out in inboxes.
✅ Ditch the one-size-fits-all discounts—use personalized offers instead.
✅ Add cross-sell and upsell nudges to capture easy revenue.
✅ Show your best customers some damn appreciation.

If you implement even one of these ideas, you’ll probably see an immediate impact.

Which one are you testing first?

That’s it for this week!

Cheers, 

Eli 💛

P.S. Looking for inspo on your next email/sms campaign?

I know you will love this.