2nd Offers and Re-engagement

Don't give up!

Jacob Rushfinn

Mar 01, 2025

Hey there, it’s Jacob at Retention.Blog 👋

I got tired of reading high-level strategy articles, so I started writing actionable advice I would want to read.

Every week I share practical learnings you can apply to your business.

Don’t give up on those users!

Win them back with 2nd offers and contextual re-engagement

We know the first paywall is the most important, but there is still an opportunity to get the 90%+ of users who don’t convert immediately.

Your goal is to build a valuable product, so even people who don’t pay immediately have a reason to come back and check you out

How do you get these users to stay or pay for your product?

Let’s look at how a few different apps approach this.

I looked at: Waterllama, Headway, Flo, Zing AI, Impulse, MyFitnessPal, Ahead, Fabulous, Ladder, Finch, Elevate, Breeze, LingoKids, Calm, Strava, Deepstash

Waterllama

Waterllama uses a limited time, discounted Lifetime offer to try to win you over. $8.99 is quite an affordable price for access forever, so I bet it does decently.

Headway

If you don’t convert on the first paywall, Headway has a mini-survey that asks you “Why?” and then tries to address those needs. This seems like an attempt to convert more users without a discount.

See all the survey options in my post here ➡️

If that doesn’t work, then Headway goes back to the more traditional discount offers:

Flo

After a period of inactivity, Flo shows a paywall that reminds me of the different value props and describes them in decent detail. I believe this $59.99 is the standard price.

Think about the mindset of your users who are returning. They are likely more familiar with the product, and coming back is a decent signal of intent, so don’t be afraid to give more detail and explanation on why they should convert.

They also celebrate 365 days since I first opened the app (this shows after the paywall)

Zing AI

After I open the app again, they show a one-time offer with a trial toggle. If that purchase fails, they do show a “Retry” modal.

There are many reasons why an in-app purchase could fail. Don’t be afraid to nudge your users to Retry the purchase.

If I still don’t purchase they work to reengage with a “What’s new” in-app message and then with different tooltips to help guide me.

These tooltips don’t pop up all at once. The first tooltip appeared, I tapped something, and came back to the home screen. The 2nd tooltip only appeared after Zing saw I wasn’t engaging.

Don’t overwhelm users with messages, but also don’t let them get lost. It’s a fine balance.

Impulse

Impulse shows a discount paywall on app open after a period of inactivity.

I’d bet they get a lot of people on the weekly trial renewing quickly and get a few periods of payments before people remember to cancel.

They don’t even show an annual plan, only lifetime.

MyFitnessPal

Shows an in-app message promoting a “free premium pass.”

Really this is just a reframing of their existing 30 day trial. No new offer.

I believe MyFitnessPal is against discounts because I rarely, if ever see them offered. They have a strong brand, many users leave and come back, so I bet they actually see conversions over a long period of time.

Could they make more money with discounts? Maybe, but it’s hard to know.

Ahead

Ahead has a hard paywall and you cant use anything unless you have an active subscription. After my first trial expired and I went back into the app they put me back through a simplified onboarding flow. (I don’t show the full thing here)

Check out two things:

The title personalization on the paywall based on your goals

and “Ahead is working on a guardian program”

Maybe they’re gathering data at this point because nothing changed based on the answers I select. But I’m also not a new user, so potentially it only changes for new users. Unclear.

The app Finch offers a “Guardian” program. It’s quite interesting:

Fabulous

Fabulous welcomes me back into the app after a period of inactivity to ask me what path I want to take.

There was no discount offer besides a free trial.

Ladder

Ladder offers 50% off via an in-app message. These in-app messages link to iOS “Offer Codes” which allows Ladder to create new offers without ever building a new paywall.

It links to the App Store, so you don’t have control over the visuals, and if they don’t subscribe, they land in the App Store (not back in your app), but it does make it faster to test new offers.

(The in-app message is likely controlled by their CRM tool)

Finch

No re-engagement offer, but they do acknowledge I’ve been gone and put me through a mini-reengagement flow. They also heavily utilize “live ops” so every month there is a new theme. They push me to get excited and engage with the seasonal rewards.

Elevate

No discount offer, Elevate instead tries to re-engage me with their widget to keep me active. Widgets can be a pretty powerful retention tactic. (if done well)

LingoKids

LingoKids go to re-engagement offer is this 60% off. I’m 98% sure it’s powered by a Braze in-app message.

This tactic of using an IAM and then linking to your paywall allows you to be constantly changing the creative and copy so users can see the same offer many times without feeling “stale”

Calm

Starts when I open the app for an offer of a free trial.

Then when I close that, they have an interesting “Unlock your special gift for

today”. I traced the sound bowl and then it rotated through a few different offers. It landed on a free piece of premium content.

I’d suspect this is a A/B/C test and different people get discounts to see what performs better (or at least I’d hope it is)

Strava

Didn’t automatically show me a paywall on app open, but when I tapped on the premium button this is the paywall it showed me. I think it’s pretty standard for what they offer to everyone.

I do like this copy: “Every 19 seconds, a subscriber hits a goal. Start chasing yours.”