The Billion-Dollar Question Nobody Wants to Answer

Hi Friends!

The next few weeks will probably be the most hectic travel weeks I’ve done in years. Tel Aviv on Saturday Night, Palm Springs for eTail at the end of February, and London at the beginning of March for Uncensored (the greatest “unconference” in the world.)

Armed with my AA Exec Platinum status (thanks, status challenge) and my Monos carry-on, I’ll still be seated in row 36B—but this time, with a pep in my step because I hAvE sTaTuS. 🙃

Travel shenanigans aside, this newsletter is a practical one for anyone in CX or Retention.

This week alone, I had the same conversation with three different 9-figure brands:

“How do I get more customers from order #1 to #2?”

Always followed by:

“If I can move that number just a little, the impact would be massive.”

Yes. Obviously. A tiny shift would make a huge difference. But that doesn’t mean it’s always the right thing to put your entire focus on. Let’s break it down.

P.s. If you are looking to hire phenomenal CX’ers that I can personally vouch for, please drop a comment here. I was made aware that some exceptional folks were let go, and I’d love to help place them somewhere great. 

This week’s newsie is brought to you by Tapcart—the platform helping brands crush mobile commerce and set the stage for stronger CX and retention in 2025.

Why Savvy Retention Marketers Are Choosing Mobile Apps to Tackle Rising CAC and Boost Loyalty 

Customer acquisition costs (CAC) are soaring, up 60% over the last five years. For eCommerce brands, this means making every dollar count—and ensuring that hard-earned new customers turn into loyal shoppers. But with rising digital ad costs and diminishing returns from traditional channels like SMS and email, savvy marketers are finding solutions in owned channels.

Unlike paid channels, push notifications are free to send and consistently outperform SMS and email in engagement. Fashion brands like Oh Polly sent 400M push notifications in 2024, fostering customer loyalty—all without increasing costs. 

For retention managers, the strategy is clear:

• Reduce reliance on paid retargeting by focusing on high-value customer segments.

• Send free push notifications to stay top of mind and build loyalty at scale.

• Create a personalized experience customers can’t ignore—FOMO-driven exclusives, personalized offers, and effortless engagement.

As Hans Harris, Director of Growth at BrüMate, explains, “Having the app lets me be more aggressive on acquisition because it’s a reliable and efficient sales channel that increases our MER. It's a huge safety blanket when it comes to scaling the most expensive channels." This CPG brand sees 43% higher CVR on the app vs their website.

In 2025’s high-CAC environment, mobile apps are more than a channel—they’re a cost-efficient retention powerhouse. Want to lower your CAC and boost retention? Tapcart’s mobile apps and push notifications can help your brand build a loyal customer base while maximizing ROI.

1. Industry Benchmarks: Are You Actually Underperforming?

Before you stress over your repeat purchase rate, figure out if it’s actually a problem.

For example, if you’re selling cosmetics and 40%+ of your customers repurchase, you’re already outperforming most of your competitors. Pushing that number higher might be an expensive, uphill battle with diminishing returns.

Instead of fixating on squeezing an extra 1% of customers into a second order, ask yourself:

• Is my business actually underperforming, or am I chasing a vanity metric?

• Would my time and budget be better spent optimizing CAC payback period and increasing AOV?

• Am I trying too hard to create new customer behavior instead of accelerating existing behavior?

Worth looking at a tool like Varos to track by industry or Yotpo’s RFM benchmarking (in beta, coming soon!)

For most brands, pushing first-time buyers into a second order takes way more effort than increasing AOV and LTV among customers who are already engaged. Sometimes, the smarter move isn’t to force another order—it’s to double down on the customers who are already showing signs of sticking around.

One brand I worked with spent months running experiments to move more customers from order #1 to #2. We tested aggressive discounts, personalized retargeting, and “exclusive” second-purchase offers. The result was a very small incremental lift.

Then, we turned our attention to customers who had already made multiple purchases—focusing on in-cart upsells, bundling, and post-purchase cross-sells. The impact on revenue was massive. 

Instead of spending thousands nudging one-time buyers to place a second order, we maximized the value of customers already in our ecosystem.

In so many cases, the easiest incremental dollar is pushing for the replenishment of the same item at a slightly sooner timeline than the time between purchases.

2. Your One-Time Buyers Aren’t Ghosting—You’re Just Not Asking Why

Brands love to send a million follow-up emails but almost never ask customers why they didn’t repurchase.

Most companies just assume:

• Maybe they hated the product

• Maybe they just aren’t the right customer

• Maybe they’re dead (okay, not really, but you get the point)

But I found that if you just ask, customers will tell you why they didn’t repurchase.

Try this instead of hammering them with promo codes and “We Miss You” emails:

• A quick, straightforward survey in an email or SMS

• A plain-text check-in from a real person

• A simple post-purchase follow-up that asks, “Hey, what did you think?” instead of hard-selling another product

And yes, this works.

Funny story: I was chatting with a store employee at a very well-known omnichannel brand. They’re famous for sending an absolute tsunami of emails and SMS and non-step aggressive ad funnels (tornados.)

I once saw the CEO in an article saying brands “don’t send nearly enough” emails and should double down on frequency.

Welp. The store employee told me that nearly every single customer who walks in complains about how aggressive their emails and ads are. People feel relentlessly hounded.

So, yeah. If your follow-ups are giving restraining order vibes, maybe rethink the strategy.

(Also, if you already know your highest-value customers, why not make their experience actually worth sticking around for? This week’s sponsor, Tapcart, lets you build a VIP-level mobile app experience for your best repeat buyers—no more spamming, just direct, personalized engagement.)

3. Your Offer Might Be Wrong (or Just Boring)

There’s a huge difference between nudging a happy customer to repurchase and trying to convince someone to buy again when they weren’t thrilled the first time.

If your first-purchase experience wasn’t amazing, no amount of discounting is going to bring people back.

This is why surveying customers is critical. You need to know:

• Was the product quality what they expected?

• Did they feel it was worth the price?

• Was shipping/delivery smooth, or was it a disaster?

• Did they even remember they bought from you?

If your first-time buyers aren’t coming back, there’s a reason—and it’s probably not because you didn’t email them enough.

TBH, this is one of the best reasons to leverage your customer reviews to segment post-purchase communication.

If someone rates your product 1-star, why are you pushing a replenishment?

Send a plain text email asking them to select a reason they did not like it, and then segment based on that. 

Example: A brand I worked with spent months pushing aggressive second-purchase discounts, but repurchase rates barely moved. After actually asking customers what was up, we found out a huge chunk of them thought shipping was too slow—so they just moved on to another brand.

Once they fixed logistics, repeat purchases jumped almost overnight. (Also, if you’re not testing with tools like Pretty Damn Quick, you’re probably leaving money on the table. Expectations set and met = fewer excuses to churn.)

4. Personalization Actually Matters 

Most brands think personalization means:
✔️ Using the customer’s first name in an email
✔️ Sending them generic “recommended for you” product lists
✔️ Offering a blanket “10% off your next order”

That’s not personalization. That’s automation dressed up as effort.

If you really want to drive repeat purchases, your follow-ups should feel like they were written by a human who actually remembers what the customer bought.

For example:

• Instead of “You left something in your cart,” try “That moisturizer you grabbed is even better when paired with [Product X]—here’s why.”

• Instead of “We miss you, here’s 10% off,” try “You grabbed our [Product] a few weeks ago—how’s it working for you?”

• Instead of “Check out our new arrivals,” try “Since you bought [Product], you might love [Related Product].”

Instead of spamming them into another purchase, try reminding them why they bought from you in the first place.

TLDR—Where to Focus Instead

If you’re already performing at or above industry benchmarks, don’t kill yourself over squeezing a few more customers into order #2.

Instead:
- Find the biggest LTV levers—bundling, upsells, exclusives, etc.
- Ask why people aren’t coming back instead of guessing.
- Make sure you’re not spamming people into oblivion.
- Fix the actual experience before throwing more discounts at them.

So, if you’re sitting there sweating over your repeat purchase rate, take a breath. Maybe the real answer isn’t forcing another order—it’s creating an experience where customers actually want to come back.

That’s it for this week. Now, if you’ll excuse me, I need to go figure out how I’m surviving 13+ hours in an economy seat (prob binging Bald & Bankrupt YT videos).

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.