Three Retention Commandments

Hi Team,

This newsletter comes to you from a Hyatt House in Salt Lake City, Utah. It's my first time here, and I'm thoroughly impressed. It is a beautiful city with a thriving ecom scene.

I was an “honored guest” at the ecom dinner hosted by Jess and Tanner and recorded a quick podcast. Twenty-four hours, in and out. 

Earlier this week, Sam put together the first-ever Retention Roundtable. Excited to share more on this as we build, and I will aim to share some of my learnings in next week’s newsletter. 👀 

Over the last few weeks, I have hit on many core retention foundations, including what to do in the first two weeks of a new job.

Advice is a dish rarely served well, especially in the Retention world. There are hardly any “best practices” that actually work across all categories and businesses.

Yet it certainly does not stop gurus from pedaling gated “value bombs” that will change your business.

Truth be told, there are very few surefire ways to “increase your LTV within x days” (great post on that here), but if you reframe your thinking, you might have a chance at this. 

Today, give me a shot at trying to change your thinking with a few pillars I have been thinking about recently.

I won’t take up too much of your time. 

Grab a chair. Let’s talk. 

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Retention Pillars Worth Losing Sleep Over:

I’ve consulted for 100+ brands in the ecommerce and tech universe over the last four years, and if I have learned anything, its this:

No two brands have the same retention unlock. Even if the problems look the same, the solution rarely looks the same. 

But some core pillars stretch across 100% of brands, and they are these. 

1. Know Thy Customer 
2. Test Properly 
3. Frequency Matters

I’ll try to make it painless; here we go: 

1. Know Thy Customer: 

Who they are: 

As marketers, we often tend to think we know the answer to every customer concern and love to drop the “they wanted faster horses” quote in an effort to tell ourselves we know what they want better than they do. 

If there is one learning I have had across most of the brands I have worked with, it’s this:

Almost none of them have a clue what their customers actually want, or what their customer behavior looks like.

I have often seen folks build a community and then use that as a place to ask customers questions.

While that is great, considering you are talking to your already top 1% of customers (hell, they joined a Facebook group of your BRAND), it won’t help you much to unlock info from the one-and-done customers or the not-super-engaged customers. 

The best two ways to get to your average Joe or Jane is actually through CX or the Retention team, either through the one-off convos your CX team has or through surveys you send via email. 

What they do:

The easiest way to keep your customers engaged with your brand is to better understand which direction the wind is already blowing.

It is easier to encourage already existing behavior than to try to create net new ones.

99% of brands sleep on this data. It is easily accessible through almost every data tool you use (Triple Whale, Peel, etc.)

100% of your customers have purchased once. Of that crew, what are the most popular purchase seuquences?

If the bulk of your customers that buy a tee shirt in their first order end up buying another tee in a different color order number two, sending emails that highlight your entire collection won’t do nearly as well as the emails highlighting the top colors of the tee they already bought first.

You obviously want to highlight other great products as well, but don’t forget the journey they are on and the already existing behavior if you are looking for a quicker win. 

2. Test Properly 

This is def not my forte, and I will spare you the neurotic details that some others can shed light on, but I will say this:

1. A/B test most large changes to your retention plan, especially changes in email/SMS flows.

2. Change on variable at a time, keep the rest as is. If you change everything, you’ll have no idea what actually drove the positive (or negative) outcome. 

3. Combine small bunts with home runs. Test the small things like the subject line and header, but also the items you cross-sell and the strategic direction of your post-purchase flow. 

4. Start with a hypothesis, and document everything. 

3. Frequency Matters

Ever wondered how some brands end up bombarding your inbox like there’s no tomorrow? 

Take Wayfair as a case study—sign up for their emails, and brace yourself. It's like opening a floodgate: an onslaught of daily emails, each one louder and more desperate than the last. It's relentless, whether you engage or not.

So, what's the deal? Why the spamfest?

It's all about KPIs. Somewhere along the way, the teams handling lifecycle marketing got fixated on a simple equation: more emails = more money.

Under the relentless pressure of hitting those monthly targets, they keep hammering away.

But here’s the kicker: As the frequency cranks up, so does the rate of unsubscribes and email fatigue. Engagement plummets, but the emails don’t stop.

They can’t. The machine has been set to maximum, and dialing it back feels like a direct hit to revenue. 

Could a more targeted, less frequent approach work better? Maybe, but who's brave enough to try when every drop in frequency hits the bottom line?

This is the email marketer’s paradox. Once you crank up the frequency, it's almost impossible to scale back without top-level intervention—and often, it’s those at the top who were cheering for the increase in the first place.

Here’s the takeaway: It’s a trap. An easy one to fall into, hard to escape. Before ramping up your email cadence, consider the long game. 

Is the temporary spike in revenue worth the potential long-term damage to customer relationships? 

Because once you’ve turned the dial up, turning it down is a battle that few are brave enough to fight. Not shockingly, it’s the same with discounts. 

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!


Eli 💛

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

I know you will love this.