You're Sending Too Many Emails (And You Know It)

Hi Team,

This email comes to you from an American Airlines flight, LHR-PHL. For the first time in a hot minute, we landed a points upgrade to BUSINESS CLASS. The points gods have blessed me on this flight.

I spent the last 48 hours in London for Retention Uncensored alongside 75 phenomenal marketers. I’ll share some high-level learnings next week—but let’s just say it was life-changing.

So excited for our third one in LA this April (brand folks, you can join folks like Hexclad and Society6 for free here).

Now, onto this week’s topic.

There’s a sentence that’s been living rent-free in my head for months, and I can’t let it go.

I took part in a panel at a conference recently. We talked about retention and personalization. There were three well-known brands on stage alongside me.

In the same breath that they preached “personalization,” one of them dropped this gem:

"You can never message your best customers too much."

I nearly fell out of my chair.

I’ve ranted about bad personalization for years. But should you even try to personalize? I assumed the answer was obvious. 

If a marketer had a magic wand that lets them send the right message, at the right time, to the right person—and make the same amount of money (or more)—they’d do it.

Right? RIGHT??

Apparently not.

The wildest part is that this isn’t just one bad take. The entire industry seems to be running with this lazy, tired groupthink that says:

➡️ More emails = more money.
➡️ You can’t send “too many” messages.
➡️ Just blast the list.

I asked around. I asked real customers—people who don’t know what ESP stands for. People like my mom.

“Do your favorite brands send too many emails?”
“YES.”

She rattled off five brands she actually likes—all of which send her 5+ emails a week about products she’s never bought or would never care about.

So why does this dissonance exist?

Why do real customers feel spammed into oblivion while email bros on LinkedIn keep telling brands, “You’re not sending enough”?

It’s not that more emails don’t make you more money. They do—but only because, in that full-list send, there are some people ready to buy who just needed a push.

The problem? The other 90% weren’t ready. Instead of using even the most basic personalization to find the ones who are close to buying, most brands take the lazy route—just blasting everyone, over and over, until they “break.”

Let’s break this down.

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1. The Tension Between Growth and Retention is Screwing Personalization

The problem isn’t just that brands send too many emails. It’s that they do it for all the wrong reasons.

Growth and retention teams are supposed to work together, but their goals rarely align. Leadership assumes they’re on the same page, but unless someone is actively managing that tension, bad things happen.

The growth team is responsible for bringing in as many new customers as possible at the lowest cost possible. Once the customer buys, they move on.

The retention team is responsible for getting those customers to buy again.

Since growth teams rarely have any accountability for what happens after the first sale, they do whatever it takes to get people in the door—overselling, overpromising, and attracting customers who are never going to stick around.

(FWIW, I think SaaS does this better because, very often, the Sales team will be in hot water if a customer churns right after they onboard.)

Let me give a quick example: A supplement brand runs aggressive ads promising that if you drink their green juice, you’ll never get a headache again. People buy. A week later, they still have headaches. They never buy again.

Now, the retention team is stuck trying to clean the mess and re-engage customers who were set up for failure from the start.

Their easiest hammer at this proverbial nail is to send more messages, hoping that, eventually, enough people will convert.

Leadership should be managing this balance, but they often don’t. More emails make more money in the short term, so they keep pushing.

The pattern is always the same. First, brands start sending more emails and texts. Then, they start relying on heavier discounts. Eventually, they realize they’ve trained customers to only buy with discounts and completely destroyed their margins.

Walking that back is nearly impossible.

2. Even Retention Teams Are Sabotaging Themselves

So many retention teams aren’t just battling misaligned incentives with growth—they’re actively sabotaging their own long-term performance by spamming their entire list without thinking about the cost of what they’re doing.

A 2024 survey of 1,400 customers from SimpleTexting found that:

• 48% of people unsubscribe from texts because brands message them too often

• Close to 50% of customers say they don’t want to receive texts more than once a week

These are real customers saying they’re annoyed. Yet most brands ignore this and keep pushing the idea that “you can never send too many messages.”

(Jack from Para, a cool SMS marketing tool that lets you send voice notes via text, shared this survey with me, and I had to dig in.)

The crazy part is how much money brands spend to acquire an SMS subscriber just to immediately lose them.

Look at the numbers:

• You pay to drive traffic to your site

• Some of that traffic bounces

• Some convert into SMS signups

• And then, because your messaging strategy is lazy, they opt out almost immediately

The entire channel becomes a leaky bucket. You spend all this money to collect numbers, only to churn through them as fast as you get them.

This is wild, considering SMS is one of the most powerful revenue channels when used correctly.

Most brands think they need to send more texts when the real opportunity is sending the right text, at the right moment, to the right person.

Instead of using even basic personalization to identify who’s actually ready to buy, they keep blasting full-list sends, ignoring the fact that most of their audience isn’t interested at that moment.

This cycle is completely avoidable, but only if brands start thinking about retention in a smarter way instead of treating it like a volume game.

3. The People Telling You to Send More Are the Ones Profiting From It

The loudest voices telling you to send more emails and texts are almost always the ones making money every time you hit send.

Most ESPs and SMS platforms charge per send. The more messages you blast, the more revenue they make. So, of course, they’ll never tell you to slow down.

Agencies are held accountable for growth today, and because customers swap agencies so often, caring about your deliverability or the long-term detriment of customer engagement is rarely their priority. 

The same goes for the “send more” crowd on LinkedIn. Most of them work for ESPs, agencies, or SMS providers—or they’re just parroting what they’ve been told.

TBH, one thing I love about Yotpo SMS/Email is that the CS team is not incentivized by the volume you send and will actively push you to send better messages, not more. Also, we hired a bunch of CSMs from the brand side (Malin & Goetz, Armra, Act + Acre) who sat in the same seat and knew how to strategize vs. sling.

Now, it’s not that sending more messages won’t make you money. It will, in the short term. But that’s not the full picture.

Instead of blasting your entire list, start with the most obvious signals:

• Browse abandonment – They looked at a product but didn’t add to cart.

• Abandoned cart – They were seconds away from buying but bounced.

• Last purchase date vs. replenishment window – If they usually reorder every 30 days, don’t send them five promo emails in the first two weeks.

• Categories they purchased from – If they only buy skincare, stop sending them promo emails for haircare.

• Review sentiment – A 5-star reviewer gets a different message than someone who left a 1-star review.

• Loyalty program engagement – If they’re active in the program, acknowledge it. If they have unused points, remind them.

• Subscription status – Don’t send “subscribe & save” offers to people who are already subscribed.

Using even a couple of these signals can reduce unsubscribes, improve conversions, and make the experience feel 100x more intentional—without needing some fancy AI-powered personalization engine.

Personalization isn’t hard. 

What’s hard is breaking out of the lazy groupthink that says blasting more is the only strategy.

That’s it for this week!

Any topics you'd like to see me cover in the future?

Just shoot me a DM or an email!

Cheers, 

Eli 💛

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

I know you will love this.