🥗 Baby Get Back - with Winbacks

Hey there,

Welcome back for another bite to chew on.

In our last newsletter, we covered why cancellation surveys are paramount in your subscription program.

Few things are more important than understanding why customers cancel.

This is the key to winning them back - today we’ll tackle this topic.

Before we get into retention and winback, let’s start with how you can treat subscriptions like acquisition…

By convincing one-time buyers to subscribe.


📖 Reading time: 5 minutes


At Obvi, we’re fairly early in the journey of embracing the subscription model. 

Right now, we’re aiming to be first-order profitable.

And treat subscription revenue as upside. 

One way we quickly boosted AOV was by bundling future orders. 

We enabled the customer to buy a one, three, or six-month supply up front. 

40% of our customers bought only a 30-day supply…

So immediately - we hit this segment with content highlighting the gains they would see at the 60 and 90-day mark. 

This flow convinced another 10% to opt in and subscribe. 

Small wins right?

Even with just a 10% lift, you’re talking about a dramatic gain in your recurring revenue momentum. 

That’s the magic of subscription -  and why we all want to make it work.

Here are two strategies you can try immediately to boost AOV on one-time purchases, courtesy of our friend Pierson Krass, founder at StayAI:

  1. Appeal to the customer’s concern for the environment. 

Try bundling a 3 month supply into one shipment to save on carbon footprint. 

This boosts AOV while saving you the shipping cost. 


  1. Throw in a freebie 

If you’re bundling 3 orders in one shipment and pushing into $100+ AOV, add a gift to the cart. 

This tactic does two things:

  • Allows you to build loyalty by making customers feel rewarded 

  • Even better, It sets up SKU flexibility for customers, making product swaps easy when they crave something new

So far, this strategy has paid off - but we’re not stopping there.

Don’t sleep on your cart.

You should have a smart cart feature to test a discount when a customer is willing to commit to auto-replenishment. 

One learning we got around acquisition was testing two different discounts: 

- Subscribe and save 15%

- Subscribe and save 20%

Can you guess what we saw?

Higher churn on the 20% since we trained these customers to expect a deeper discount.

And LTV was a lot lower. 

You should be A/B testing right in your cart to learn the LTV upside your brand can unlock.

Getting commitment to subscribe after the order. 

We’ve found that new customers less familiar with our brand may not subscribe on their first order. 

So what are some ways to move them towards subscription? 

If we take a step back and really do this right, there’s some work involved – but it can have a big payoff.

Laying a solid groundwork from the start is the way.

Do this by creating amazing storytelling for your customer personas…

This will inform the perfect messaging for product education later in the subscriber journey.

We all want to move beyond lazy offers and discounts, right?

What do different personas look like? 

  • Some customers only respond to discounts. 

  • Your best customers want to engage with your brand on a deeper level. They participate in your community, supporting each other. 

  • Fanatical customers want to be part of your product development process. You want more of these.

Yes, it’s extra work - but treat each of these personas with unique messaging and flows. 

Building on the foundation

You did your homework. 

Now, run 2-3 separate offers or funnels from your core site to lead to your subscription offers. 

This will be your testing ground to learn messaging angles that move away from price-based selling.

Analyze what messages resonate with different demographics/psychographics to evolve your segmentation strategy.

Over time, you'll develop a messaging framework that nurtures the right customers at the top of the funnel

And you’ll know what education works for customers lower in the funnel to keep them coming back for more. 

From this foundation, you’re ready to introduce new subscription flows… here’s how:

We talked about testing on the cart above. That’s a no-brainer.

Turn one time orders to subscriptions

Ok, so they purchased a one-time supply. 

Maybe they’re feeling a bit of buyer’s remorse knowing they haven’t fully committed to what they know your product can do for them. 

Here’s a quick way to increase post-order subscription opt-in: 

Offer them an instant $5 back on the order they just placed.

Within that flow, let them customize the delivery cadence that works best for them. 

Buyer’s remorse gone! They feel committed to their goals, while taking control of replenishment timelines

Keep AOV rising with quick actions.

A lot of brands are seeing success with quick actions. 

This is where you can drop an offer at any marketing touch point prompting the customer to add products to a subscription.

You can do all this by partnering with Stay.ai.

In fact, our Obvi subscription portal is powered by Stay.ai

We focus on ensuring our portal isn’t just a place to cancel. 

Realize its potential to be the heart of your CX fostering education and upsells. 

A key portal metric we measure is the ratio of negative (cancel/pause) to positive (subscribe/add-on) customer interactions.

Brands that are crushing it see over 60% positive, revenue-boosting portal engagement.

When they don’t want to stick around 

You’ve worked hard to know your customers.

But the unthinkable still happens and a customer wants to cancel.  

When you’ve been operating a brand for years, your winback cohort becomes a big opportunity to revisit.

What can you do?  

At this point, you’ve done the hard work of setting up flows that address cancellation reasons. 

You’ve tailored product education to individual customer personas. 

A good tactic is to apply your product education to what you know about this subscriber.

Present an offer that addresses the reason they canceled. 

For example, if they didn’t like a flavor, let them swap to other options in the reactivation quick action. 

Unlock new tactics you can use with an enhanced winback engine

Doing the upfront work on messaging by persona is the foundation for successful winback strategies. 

From there, having all of your tools work together to engage the customer where they are  

- Email


- Direct mail

- Social 

- Etc 

Conditional blocks (powered by Stay.ai) allow customers to easily reactivate their subscriptions with one click from anywhere. 

Don’t just offer discounts, make sure you are using messages that help drive accountability around your value prop

Try headlines that say “Building healthy habits” 

Or “You're this much closer to beautiful skin” 

Got a new, exciting flavor to share? Send an SMS asking which new flavor they prefer. 

You might just reactivate a churned customer with a single text!

Tool of the Week 

We want you to do one thing right now…

Take a look at how you’re running your marketing operations and answer us this:

Is it a well-oiled machine or are you juggling multiple platforms with your thousands of customers?

How’s that working out for you?

You probably have numerous email flows like post-purchase, abandoned cart, and winback automation funnels to drive sales – and several sub-flows attached to each

So did we – but running these communications on several platforms was killing our potential impact.

And we understand – you’re assuming moving to another tool is going to bring everything downhill

Like migration taking forever, email deliverability dropping, and more

But I promise you – put some socks on those cold feet and unify marketing ops with Sendlane

Immediately their incredible team calmed all of our nerves and was there for us every step of the way. 

Their onboarding team not only made sure we had a smooth migration but also leveled up our strategy – by moving email and SMS to one platform, they were able to:

Clean up our contact database and increase subscriber value by 32%

Upgrade automation flows

Add fresh email content that increased click through rates 8%

And create new customer segments based on missing attributes

On top of all of that – the best part is their 'Move Now, Pay Later' offer. 

You pay nothing upfront. No hidden fees, no unexpected bills during the switch.

They take over the entire migration process—transferring data, warming up emails, everything and you won’t pay a dime until you’re fully warmed and sending.

So, if you’re dragging your feet on a migration because you're worried about the costs, disruptions, or just the sheer amount of work it might take, 

It’s never been a more efficient time to move to Sendlane.

Smooth migration with no bumps in the process + an amazing team to do it all for you.

Upcoming Events

SubSummit is right around the corner… do you have your tickets yet?

RSVP and get on the list for our June 17th event hosted at SubSummit here!

Thanks for Reading Along

We hope this edition gives you lots of ideas for winning back churned subscribers. 

In summary:

  • Ace your cancellation flows & insights

  • Build your persona framework 

  • Proactively communicate with customers to keep them engaged 

  • Give customers full flexibility to control their delivery cadence/quantity

  • Turn your subscription experience into a product education hub

Got any questions or want to share a tactic we didn’t cover?

Reach out and tweet us - Ron’s Twitter - Ash’s Twitter

We love getting to know what you’re doing for your brand. Be sure to keep in touch! 

Until next time,

Ron and Ash