"When is the best time to ask a customer to subscribe to your brand?" is one of the most common questions we get. Unfortunately, it’s also a hard one to answer because the brand and the customer usually have different objectives.

Before we answer that question, we must understand the customer's motivations behind when/why they want to subscribe.

Why do customers want to subscribe?

The easiest way to think about this is to ask yourself why you subscribe. Is it to get a discount, for convenience, or something else?

DTC brands have historically over-indexed on the idea that subscriptions are about the convenience they provide customers.  Yes, it can be very convenient if the timing and amounts are just right. Otherwise, the wrong quantities can actually become quite inconvenient.

Eli Weiss on why customers want to subscribe


In a previous episode of Customer Hat, Eli Weiss said that a subscription today is more or less a handshake to enter into a long-term commitment to each other. The brand provides consistency and a discount, and the customer provides long-term support and consumption.

But as Eli stated, if you want customers to subscribe, it has to be about more than offering a good discount to do it. Otherwise, you incentivize one-time purchasers to subscribe and then churn in month one.

So… why do customers want to subscribe?

  • Trade a commitment for a more favorable price
  • Consistency mixed with a bit of convenience
  • Feel like they belong to something with the brand

This feeling of belonging is why many brands are evaluating running pay-to-join membership programs alongside or in place of subscription programs. But before a customer sees value in these benefits, they have to make it deep enough into the customer journey.


What does a customer need to know to subscribe?

customer needs to know before they commit. The easiest way to do this is to think about what holds you back from subscribing to a physical product.

These questions come to mind:

  • What if I don’t like it?
  • What if I get too much of it?
  • What if I find something better?
  • What if I need to change it later?


These hesitations hold people back from subscribing, and are why many brands elect to build a subscription explainer page. Here are a few that brands in CPG House admire.

CPG House shares subscription explainer pages they admire

While you can ease people’s minds with a subscription explainer page, the best way to get people comfortable is to have them understand the answers to those questions through usage.

Usage takes each customer down a purchase journey, eventually making them a better subscriber.


The customer journey to subscription

I promise I will get to the answer of when to ask a customer to subscribe, but let's first look at where a subscription naturally fits into a customer’s purchase journey.

Generally speaking, the way someone ends up consuming consumer packaged goods (CPG), and other products that have a replenishable nature, looks like this.

Discovery > Trial > Repeat > Loyalty

To make things as simple as possible, a customer must first discover your brand and try it. That's when the fun starts. You might think this is an ok time to consider offering a subscription, but that customer still needs enough repetitions to understand if it will become a part of their routine.

Discovery: A customer needs to know your brand exists to try it. Discovery can happen through paid ads, retail availability, or word of mouth.

Trial: Once a customer is aware of your product's existence, they must actually try/use it. Once they do, they may move to repeating the use quickly, but they might also need to try another product before they find the one that's for them. Flavor, scent, and other factors all contribute to whether a customer is willing to buy that product again.

Repeat: This could be considered the point at which a subscription begins to make sense. The customer liked the product enough during the trial to use it again. Most people, however, still are not committed at this point; this is when a few repeat purchases allow them to understand their usage before fully adopting it into a routine.

Loyalty: When customers have found a product and used it enough to adopt it into their routine, they have become loyal. They become much more likely to adopt other products and are very receptive to your campaigns and offers. Do not mistake loyalty for subscription, though. You can have a loyal returning customer, even if they don’t subscribe.

Now that we understand what the customer needs to get from you, the brand, to subscribe, let's tackle the big question.

When should I ask a customer to subscribe?

There is a straightforward answer to this question, with a few stipulations. Though the answer is simple, the execution is difficult.

Ask for a subscription once the customer understands the product and usage

This statement raises another question: when does a customer understand the product and their consumption? Unfortunately, that depends on what you sell and to who. I can tell you that it’s not before the first purchase, and it's not after a single purchase.


Customers need to be able to trial and repeat before understanding how they consume a product. I did a poll on Linkedin where I asked how many purchases people need before subscribing. The popular answer is more than three, but this sentiment is also shared by CPG retention marketers that obsess over the subscription experience like Chandler Dutton from Magic Spoon.

The number of purchases a customer wants to make before subscribing

This sentiment, that someone is more likely to subscribe after a few purchases, is something that Chandler at Magic Spoon sees as well. Not only are they more likely to subscribe, they are also less likely to churn, he finds.

There are obviously a bunch of stipulations to this rule. If you want to get into those nuances, like what if people have already tried the product in retail, you can listen to our full conversation about subscription strategy with Chandler.

Chandler Dutton, Director of Retention at Magic Spoon, shares his views on subscription strategy


Without overcomplicating it, the right time to ask someone for a subscription is when they are in the Loyalty phase of the customer journey. At minimum, thats going to take two purchases.

Oversimplified, the right time to ask is once a customer has 2+ purchases under their belt

Alright we finally know when to ask a customer to subscribe, but how should you go about asking them to do it?

How do I ask a customer to subscribe?

If you wait until purchase 2 to offer a subscription, how should you actually ask someone to subscribe?

More great questions that have both an easy answer, and a more nuanced one. The simple answer is that you should ask them post-purchase via email or SMS. With flow builders like Klaviyo, you offer a subscription with an automation that fires a certain amount of days after the second purchase.

There is a way to ask for a subscription that also increases the chances of a repeat purchase for those who might never subscribe. There are a lot of us out there, including myself. I’m very subscription averse.

How many physical products is the average person subscribed to?


Repeat replenishment flows are triggered based on your store’s reorder interval data. That way, an invitation to buy again is always delivered at the most opportune time. This timing allows people to continue through the “repeat” phase of the journey as efficiently as possible.

And, you can now invite customers to subscribe directly from these reminders. That wa,y no matter how many orders it takes to move to “loyalty,” you are ready and waiting with the offer to let them subscribe. The best part is that even if they aren’t ready, they can easily reorder via the Repeat cart.

Subscription upsell via the Repeat Cart


It really comes down to giving your customer agency on how they prefer to reorder and move through the customer purchase journey.

The TL;DR of when you should ask a customer to subscribe

There is no one size fits all answer to this question. The truth is you need to dig deep, analyze, and experiment to truly figure it out for you and your brand. I hope this article has given you a few mental models to think through to understand your customers' motivation for subscribing.

You can get a head start when you know what motivates the customer.

Here’s the head start I would take:

  • Make OTP the default to encourage trial
  • Allows people to easily reorder without requiring a subscription
  • Encourage product usage (2 orders) before asking for subscription
  • Build a subscription upsell campaign to trigger after two orders
  • Use Repeat and our subscription upsell

Want to give your customers more agency over how and when they subscribe? Grab some time with us, we will show you how.

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