The Retention Filter I Use to Avoid Wasting Time

Hi Team,

More sun, less seasonal depression, I hope?

This was our last full week before we wrap up a month in Tel Aviv, and it flew by. I’m excited to get home, settle in, and finally unpack from the move we made right before this trip.

Over the past two weeks, I spoke to four brands working on their H2 retention strategy. Every one of them asked the same thing:

How do we decide which big swings to take?

There are so many things you could do. Campaigns to launch. Flows to tweak. Segments to explore. But how do you figure out what’s actually worth doing?

It’s a question I’ve wrestled with for years, and one I come back to often. This week, I want to share how I think about it.

Let’s dive in.

This week's newsie is brought to you by Portless.

What's more expensive than tariffs? Missing the summer selling season entirely.

While competitors' inventory sits on a boat:

• You could be restocking best-sellers in 3-5 days

• Selling within days of manufacturing

• Freeing up more working capital

• Paying tariffs only after customers pay you

Portless turns 6-week delays into 6-day deliveries directly from China. Take back control of your summer season. Schedule a risk assessment today and start leveraging tariff deferment today.

The Retention Prioritization Problem

One of the hardest parts of retention work is deciding what’s actually worth doing. Once you start digging, the list gets long fast.

Should we overhaul our loyalty program?
Should we build a better post-purchase journey?
Should we create different flows for each SKU or category?
Should we try direct mail? Bundling? A quiz? A pop-up?

All of these can work. But that doesn’t mean they’re worth your time right now.

The problem isn’t a lack of ideas. It’s a lack of clarity on how to choose. And when everything falls under the “retention” bucket, it’s easy to either try to do too much or to do the wrong things.

I’ve watched teams spend months on retention projects that changed nothing. I’ve also seen small changes drive massive impact when done at the right time.

When retention is treated like a checklist, the default is to focus on what’s unfinished or shiny. But that’s not how you build real outcomes. It’s not about doing more. It’s about doing what matters most right now.

The Retention Filter I Use

Here’s how I actually think through what to take on:

Start with the business problem.
Are we trying to increase LTV? Cut churn? Improve repeat purchase rate? Push subscription? Sell through bundles? The goal shapes everything else.

Then, look at the data.
Are you losing customers after the first order? Are repeat buyers not converting to subscription? Are high-LTV buyers all in the same SKU or AOV bracket? Where are the real drop-offs?

Now ask:
If I could only do one thing over the next quarter to move this number, what would it be?

From there, I use a simple test:

• Will this meaningfully shift behavior?

• Will it reach the right segment?

• Can we get this live fast enough to measure it?

If the answer is no, it’s usually not the right bet right now.

Here are a few projects I’ve said yes to in the past:

• Adding post-purchase cross-sell based on top bundles

• Building a first-to-second-order conversion flow

• Creating a quiz to push into the second SKU

• Sending direct mail to high-AOV one-time buyers

• Launching a better subscription landing page for returning customers

And here are a few I’ve passed on:

• A loyalty refresh with no clear value gaps

• A new referral program when only 10 people were using the old one

• A hyper-personalized campaign that would have taken 3 months to build

The right project has to match both your goal and your moment. Some things are a great idea six months from now but a complete distraction today.

The Impact–Lift Framework

When I’m weighing a few different options and nothing is clearly rising to the top, I fall back on something I’ve used for years: Impact–Lift.

Here’s how I think about it:

Impact

If this works, how much will it actually move the metric I care about?
Not “is it cool” or “do I like it.” If this thing performs, does it matter?

Improving your second-order rate by 5% might be worth 7 figures.
Fixing your winback email might save a few hundred customers.
Not every win is equal.

Lift

How much internal lift will it take to make this happen? Is this a one-email tweak or a six-week sprint across CX, creative, and dev?
Does it require new systems, approvals, or channels you’ve never touched?
Does it touch customer support, ops, or the PDP?

High-lift projects might be worth it, but they better be needle-movers.
For lean teams, you have to be ruthless.
Your calendar isn’t infinite. The lift of one thing is the opportunity cost of another.

A few ways I’ve used this filter recently:

• A brand wanted to create a whole post-purchase flow just for one SKU. But that SKU had low volume and low LTV. The impact was low, the lift on their team was high, and the effort was significant. We skipped it.
  

• Another brand wanted to build a reactivation campaign for customers who used to subscribe. The impact was solid, the lift was reasonable, and it could be done with a simple flow and offer test. That one moved forward.

What to Take On, and What to Leave Alone

The best retention teams aren’t the ones doing the most. They’re the ones doing the right work at the right time. They stay focused. They don’t chase noise. They don’t build for the sake of building.

Every brand is at a different stage. For some, fixing a leaky welcome flow is the highest ROI thing they can do. For others, it’s about pushing second-purchase rate, unlocking category depth, or turning subscription into a real program rather than a checkbox.

There’s no single blueprint. But if you start with a clear goal, look honestly at your data, and apply the Impact–Lift filter, you’ll make better decisions, and your team will move faster without burning out.

You can’t do everything. That’s the point. So choose what’s worth doing.

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. If you want to figure out how to get your brand to rank high in LLMs and show up in ChatGPT, Gemini, and more… check this out.