Five Ways to Actually Fix Subscription Churn

your churn is not a billing problem, it's this

Hi Team!

Welcome to the summer chaos where pickup, drop-off, and camp laundry somehow fill half my spare time.

This is newsletter #197, and while I’ve covered more topics than I can count, there’s one topic I get more emails and consulting requests about than almost anything else:

Increasing subscription LTV.

More brands than ever, especially in CPG and supplements, are pushing subscription as the default and doing whatever little hacks they can come up with to juice recurring revenue. Some of it works, but some of it feels like it was brainstormed in a room where nobody ever tried to cancel anything online.

Most subscription retention problems are expectation problems dressed up as billing problems.

Brands treat retention like a dunning issue or a cancellation flow project. Delay the churn event, add a discount, make the portal a little more annoying, force the customer through three screens and hope they get tired…

By that point, the customer already decided.

They’ve been annoyed for weeks because the product timing, quantity, or frequency stopped matching their life. The shipment shows up and they already have three bottles in the cabinet. Or they ran out two weeks ago and forgot to order. Or they didn’t see results and assumed the product wasn’t for them.

At that point, the retention moment has passed, and the cancellation is more of a formality

This week, I want to talk about five levers that actually move subscription LTV, and why most brands are optimizing the wrong part of the funnel.

Let’s get into it.

This week’s newsie is brought to you by my friends at Hoop!

(Hoop is one of the newest tools I found and one I highly recommend checking out)

Brands pour a huge chunk of their budget into acquiring new subscribers. On average, 50 to 70% of those subscribers churn before month 2.

Stop and consider that for a moment: you paid an expensive CAC for that revenue, and most of it walks out through a cancellation ticket or self serve flow that gets closed with a polite confirmation. You don’t know exactly why each subscriber cancelled, and you didn’t make a reason based offer to help them stay.

So what can you actually do today to keep more of those customers for longer? That’s exactly what Hoop does, out of the box. Built by the team behind Trello, it runs the save conversation on every cancellation:

- Asks why before offering anything: then matches the offer to the specific reason (product education, price, a product swap instead of a cancel, and fully customizable based on your brand)

- Reads full subscriber context: from systems of record like Shopify and Recharge or Skio

- Works inside Gorgias, Zendesk and Kustomer: No new tools, no migration.

MoonBrew, a scaling sleep supplement brand, went live in about a week and hit 24/7 coverage within a month, for roughly the cost of one agent instead of five.

Their team stays on the complex, high-touch conversations while Hoop handles cancellation requests and boosts save rate.

Since launch, not one customer has asked to “talk to a human.”

Want to see how much revenue you could be keeping?

Take the free audit: Hoop reads 90 days of your helpdesk tickets and hands you your baseline save rate, why subscribers actually leave, and the annual revenue you’re leaving on the table.

The first purchase doesn’t need to be a subscription

Most brands are obsessed with converting the first purchase into a subscription because it makes the dashboard look clean. Higher attach rate, prettier LTV projection, easier forecasting.

The problem is that forcing a subscription on the first purchase can suppress AOV, attract discount-chasers, and set the wrong expectation from day one. Someone who says yes because you offered 20% off isn’t the same as someone who says yes because they already know they want the product every month.

Sometimes the better long-term customer is the person who buys a larger one-time bundle, uses the product for six weeks, understands the value, and subscribes later with actual intent.

The subscription funnel gets optimized to death while the OTP path is treated like a waiting room. Brands spend all their retention energy on cancel flows and almost none of it on turning high-intent one-time buyers into subscribers after they’ve proven they like the product.

That customer often has better intent and fewer “wait, why am I being charged again?” vibes.

Save offers should match the cancellation reason

A lot of cancellation flows are basically Mad Libs. Customer clicks cancel, brand says, “Sorry to see you go, here is 20% off.”

Doesn’t matter if the reason was price, quantity, timing, product fit, travel, moving, or the customer having six tubs of greens powder in the pantry. Same sad offer every time.

A discount only helps when price is the actual problem. If the customer has too much product, 20% off is just a cheaper way to make the problem worse.

If someone has too much, offer pause or skip. If price is the issue, offer a smaller bundle or lower frequency. If they didn’t like the product, offer a swap. If they’re traveling, delay the shipment. If they didn’t see results, reset expectations or send usage content.

The save offer should solve the reason they’re leaving. Otherwise you’re just bribing them into one more billing cycle they’ll resent.

Frequency is retention

This is probably the most underrated lever in subscription retention, and the one that kills LTV for consumable brands.

Most subscription churn is less of “I hate this brand” and more of “I have too much of this product sitting in my cabinet and I can’t keep up.”

Funny enough, this was our #1 churn reason at OLIPOP way back.

This is huge for supplements, coffee, skincare, pet, household, beverage, pantry, basically anything that gets used up.

If you ship a 30-day supply every 30 days and the customer only uses 22 days’ worth, they’re building backstock after every shipment. After six months, they have a small museum of your product in the cabinet. That’s when they cancel.

Let customers set frequency. Make skip easy. Use first-order behavior to suggest the right cadence. If someone buys a 60-day supply as their first order, please do not default them into a 30-day subscription like a lunatic.

OTP customers aren’t failed subscribers

I saw Olivia Kory from Haus post a clip from Andrew Faris on this, and it put words to something I’ve been seeing in audits.

Subscription customers look amazing in the first 90 days because LTV front-loads nicely. Recurring revenue, predictable orders, easy modeling. The dashboard gets all dressed up and tells everyone the strategy is working.

Then you look six or twelve months out and the gap between subscribers and non-subscribers can get a lot less dramatic.

One-time buyers often have higher AOV on the first purchase because they weren’t chasing a subscription discount. They have lower first-order friction because they didn’t have to opt into recurring billing. And if your replenishment marketing isn’t terrible, they come back.

The mistake is treating subscription as the only retention path and OTP customers as failures.

OTP customers can be retained. They just don’t show up as neatly in the subscription dashboard. You have to work a little harder to bring them back, but the economics can be just as strong, and sometimes cleaner because they’re not locked into a cadence that stops matching their life after three months.

The OTP funnel is under-optimized because subscription makes the spreadsheet feel safe. That doesn’t mean it’s always the better customer experience.

Cancellation is not the first retention moment

Most brands wait until someone opens the cancellation portal to “do retention,” which is completely backwards. By the time a customer clicks that button, they’ve already made the decision. The portal is just where they go to make it official.

The better retention levers happen way earlier. Onboarding sets expectations. Usage education helps them get results. Delivery timing prevents backstock. Failed payment handling catches accidental churn. Support moments build or destroy trust.

All of that happens before cancellation.

Save flows still matter, especially when they respond to the actual reason someone is leaving. The bigger win is making sure the cancellation data changes the business. If 40% of cancellations are “too much product,” the problem is not your save offer. The problem is your default frequency.

By the time the customer is in the cancellation portal, the brand is already playing from behind.

Most subscription brands are optimizing the cancellation moment and ignoring the decisions that happened before it: first purchase path, save logic, frequency setup, OTP retention, and the early customer experience.

That’s why so many subscription programs look good on paper and bleed out in month six.

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 💛