#364 - Cracking the Code on Retention: Recharge CEO Reveals What Best-in-Class Subscription Brands Do Differently

31 Oct 2025 · 44 min · 20 chapters

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In short

Retention and churn in subscription e-commerce—what “best-in-class” subscription brands do differently, and how Recharge helps optimize the full funnel (acquisition → conversion → retention).

Guest backgrounds

Ashin O’Connor, CEO and founder of Recharge. Background in art/architecture and economics; taught himself programming; previously ran a nonprofit startup (~10 people). Co-founded Recharge with Mike (CTO) after meeting Shopify’s Harley.

Key claims

  • Recharge hit 100M subscribers and 100M annual revenue; powers 75% of Shopify subscriptions.
  • Subscribers are ~4x more valuable than one-time buyers; “subscription by default” converts ~3x more than offering subscriptions later.
  • Healthy benchmarks: second order (order 1→2) retention 70%+; order 3 45%+.
  • Biggest retention lever is fixing the first 30 days (onboarding/education) and cancellation prevention.

Notable examples

  • Early merchant: Cachava (now a nine-figure business).
  • Legacy brand example: 15% of customers acquired in 2000 still buy decades later.
  • Early Recharge merchants included unusual products (e.g., cockroaches/Komodo dragons on subscriptions).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Ashin's Journey to Recharge

2:08 to 3:57

Ashin O'Connor shares his background and journey to founding Recharge.

“Why don't you give us a little bit about your background, what Recharge is all about, and maybe how you got into building the company in the first place?”

The Birth of Recharge

3:57 to 5:46

Discussion on the development and launch of Recharge's subscription service.

“And so they started to open up Facebook lookalike audiences.”

Building for Subscription Success

5:46 to 7:56

Ashin explains the challenges of enabling subscriptions on Shopify.

“And it was like, basically, people always ask you, do you know what product market fit is?”

Identifying Key Brands

7:56 to 9:33

Ashin discusses early brands that adopted the subscription model successfully.

“is so important because like you want to do both, right?”

The Power of Subscription

9:33 to 12:03

Exploring the long-term benefits of subscription models for businesses.

“We're like, oh, wow, there's going to be a lot more companies like looking like them that will come on.”

Challenges and Strategies in DTC

12:03 to 14:00

Insights on building a DTC business, including competition and customer acquisition.

“And I think this is a super important point.”

Evolution of DTC TV Advertising

14:00 to 14:59

Learn how the landscape of direct-to-consumer TV advertising has changed over the decades.

“And, you know, actually, last year, we migrated over this company called Guthy Ranker.”

Key Characteristics of Successful Subscription Brands

15:00 to 17:28

Discover the essential traits that make subscription businesses thrive in a competitive market.

“is like the types of companies that advertise, right?”

Building an Effective Conversion Funnel

17:29 to 19:36

Understand how to optimize your sales funnel specifically for subscription models.

“Then I think the second is people understanding the acquisition funnel, right?”

Strategies for Reducing Churn in Subscriptions

19:37 to 22:20

Learn strategies successful brands use to minimize churn and retain subscribers.

“What components of PDP, cart, like, how does it all play together from anywhere from the top of funnel to the place the experiences in the cart or the checkout to, you know, create a great conversion experience?”
Show all 20 chapters

Utilizing Analytics for Customer Retention

22:21 to 25:06

Explore how analytics can be leveraged to improve customer retention rates.

“hey, here are the benchmarks you want to be hitting.”

Innovative Tools for Managing Subscriptions

25:07 to 28:06

Discover the latest tools and technologies that enhance subscription management and customer experience.

“And so for us, it's like one, we got to give you the analytics so that you have the data to understand like, oh, hey, here's my cohorts that I'm acquiring.”

Enhancing Subscription Retention with AI

28:06 to 29:50

Learn how AI tools can improve subscription management and customer retention.

“And we can all think about this as a shopper ourselves is oftentimes the issue you subscribe to these physical products, you end up getting too much of the product or you get versions of the product you don't want.”

Long-Term Customer Relationships

29:50 to 31:37

Explore the importance of building lasting relationships with customers for sustainable growth.

“And you've got like this overlap between what's happening in subscription, what's happening in support, what's happening in conversion, what's happening at the Shopify level.”

The Complexity of Customer Experience

31:37 to 33:37

Understand the multifaceted nature of customer experience in the subscription model.

“And then I think the other point there that's just so important is like, you know, customers or people like they don't really care about software, like even recharge.”

Navigating the Subscription Landscape

33:37 to 36:18

Gain insights into the competitive subscription landscape and Recharge's position.

“Congrats on hitting the 100 million subscriber and ARR milestone.”

Future of Subscription Services

36:18 to 40:05

Discover the future direction of subscription services and innovation at Recharge.

“Like, here's a couple like quick wins that, you know, you guys obviously aren't doing.”

Common Mistakes and Experimental Strategies

40:05 to 42:03

Learn about common subscription mistakes and effective strategies for founders.

“And it's so cool how you started as like the subscription platform and that's like your core thing.”

Strategies for Subscription Success

42:03 to 42:41

Learn effective strategies to improve customer retention in subscription models.

“You can use our car checkout, post checkout tool or another one for that.”

Connecting with the Community

42:41 to 43:34

Discover how to engage with customers and the importance of communication.

“And for anyone who's looking to learn more about yourself all along, I love the content that you've also been posting on LinkedIn.”
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Transcript

Automatic transcript. May contain errors.

0:05Oisin O'Connor:This is D2C Pod, where the worlds of creators, consumer goods, and brands collide. We get behind the wheel to show you how today's biggest products and ideas are made, launched, and scaled. If it's shaping the future of commerce and culture, you'll hear it here first. Catch new episodes weekly on Spotify, Apple Podcasts, or d2cpod.com. Be sure to check out our newsletter for weekly breakdowns and recaps linked in the show notes. So before we kick off today's recording, I've got one more for you. E-commerce costs are rising. USPS changes alone could push delivery costs up more than 25 % this year.

0:40Oisin O'Connor:And to stay competitive, you need a supply chain partner built for scale. And that's what Stored is, a modern 3PL that unites warehousing, fulfillment, and transportation with cloud software for full visibility and control. In 2024 alone, Stored saved customers$130 million in parcel fees and powered nearly 1 % of all US Black Friday and Cyber Monday sales. Now they're offering a free mystery shopping report. See how your ops and logistics stacks up against competitors with real actionable insights. Get yours at stored.link slash mystery and scale smarter with stored.

1:18Oisin O'Connor:What is going on DTC pod today? Super excited for our recording. We've got the CEO and founder of Recharge. That is Ashin O 'Connor on. I'm really excited for this episode for a couple of reasons. Number one, Recharge is a major player in the subscription space of e-commerce. they recently hit 100 million subscribers and 100 million in annual revenue. So you can think when you think of subscription in e-commerce, you automatically think of Recharge. And another reason is it's a brand that or it's a company that we've worked very closely with. I myself operate a brand running on Recharge. You know, it's something that consistently when we have some of the brands that come on D2C pod, they're constantly, you know, scaling and they serve some of the biggest subscription brands in the space.

2:05Oisin O'Connor:So without further ado, Ashin, I'll let you kick us off. Why don't you give us a little bit about your background, what Recharge is all about, and maybe how you got into building the company in the first place? Yeah, totally. Thanks so much, Blaine, for having me on. Background. So I went to school originally for art and architecture, then economics. Then I taught myself to program, so I became a programmer. Had a startup in the nonprofit space before Recharge. So I was very like minded on I always wanted to help people and empower them. Like that was always the core of everything I did. That startup kind of like, you know, it got to about 10 people.

2:44We kind of like put on autopilot and I got to a point in my life. I'm like, OK, well, what's the next thing I want to do? Right. To build out.

2:51Oisin O'Connor:And this was about 12 years ago. And, you know, I met my co-founder around that time, Mike, who became my CTO. and we were like, okay, why don't we cold call and we hit up all the smartest people we can get a hold of in the world and ask them a simple question. If you were going to start a company today, what would you start, right? Because they were like, there's a lot of people who have way better knowledge than us of like what actually is the right thing to go after, right? And so we went through that process and one early person that we hit up was Harley at Shopify. And at the time, Shopify was only 100 employees.

3:25So they were super small, this sleepy company in Canada. and he basically sold us on on commerce on shopify on d2c and you know you know in those conversations it wasn't just harley sold us but it was like half the people told us we should go into commerce the other half said we should go into crypto so that that was our 12 years uh i really enjoyed that i went into commerce because i think i like working with entrepreneurs i like building businesses i definitely should have put more money in bitcoin but that's a different story you know um so anyway so we got in into shopify 12 years ago and we were like okay we truly believe in this wave this small canadian company we think it could be massive shopify was only you know 100 or so employees you know there was you know maybe you know 10 000 merchants on the platform right but we saw it and you know at the time the big structural change that we saw was that facebook was starting to get really good at advertising and targeting, right?

4:25And so they started to open up Facebook lookalike audiences. And we realized like that created distribution, right? For merchants to actually sell products and scale. So we got in the space and we were like, okay, we believe in the wave. We believe in where it's going to go. But what do we build, right? And so what we did is we started an agency so that we could actually get really close to merchants, build products for them, be partners with them. and we started to launch different software products. So over the course of a year, we launched seven different products and Recharge happened to be the seventh product that we launched in that year.

5:02So yeah, and we did loyalty products, we did email products, we did like an early B2B warehouse product. We just did everything. And the idea was like, we love the audience, we love the entrepreneurs, but what do we think was gonna be a really truly big problem and opportunity for us to go after, right? And, you know, I like to say that I'm the one that came up with the subscription idea, but I actually was a lot of we voted against it amongst the three of us early days. I was like, oh, who's going to subscribe to a physical product? Can't you just go to the store and buy most of those products?

5:35But we're like, fuck it. Or I guess it can't cost on these things.

5:38Oisin O'Connor:Yeah, you say whatever you want. Yeah, right. But anyways, you know what? We launched subscriptions and it just took off from day one. Right. And it was like, basically, people always ask you, do you know what product market fit is? And I'm like, if you have to ask that question, you have an issue. You just know. It's like hitting a vein. And early days, when we first launched subscriptions, all the merchants we had were pretty weird. I'm going to be honest. It was things like cockroaches on subscriptions, Komodo Dragons on subscriptions. We had a company that sold, their slogan was, it's better than cocaine, but it's legal.

6:14I still don't know what that company does, but it was one of our top merchants. So we just had all these like weird early adopters to the model, but we could tell like there was going to be something big there. And so that was kind of our early days of how we got into subscriptions into Shopify.

6:29Oisin O'Connor:And what did that landscape look at the time, right? Because like you're saying, Shopify is like 100 people, you know, subscription wasn't super popular on e-com. Like what did you need to build to enable it? Where was the opportunity? Why wasn't Shopify supporting it? and what did you guys need to do at the MVP level to enable this behavior? Yeah, totally. So I think the big thing is they're actually, so Shopify had launched their app market like a year or two years before that. And they actually had done this whole competition, like spent a couple of million dollars in prizes for people to build apps into their ecosystem.

7:01And basically there was a bunch of subscription apps, right? So there was like 10 different apps in the market, but they all were kind of shitty. And what they did is they basically, So Shopify didn't natively support subscriptions. So what you would have to do is when someone buys a subscription, you would have to go to a third-party checkout that this app would control, and then people could buy it there. And so what every app did is that you could go to this other checkout and you could buy a subscription, but you couldn't buy the one-time items and subscriptions together. And you couldn't also have a way to handle taxes, shipping, discount codes, and a customer portal for the end shopper, right?

7:41So there was just like a lot of like basics that a physical product company selling subscriptions would need versus like a digital product, right? And so we basically built out these like core building blocks and that's what like really differentiated us early days and took off.

7:56Oisin O'Connor:Yeah, and I think even just that little distinction is so important because like you want to do both, right? You want to be able to sell it as a one-time product for the person who wants to try it out and you want to sell it as a subscription product for the person who's totally bought in. And like, even if you can't just do that little thing, it totally changes the equation. Even like us, when we were getting set up on recharge, like that was like, it's one of the non-negotiables. It's like, I don't want to create a different SKU for this. And like, you've got all the ways it ties into your 3PL.

8:24Oisin O'Connor:I'm like, I want one SKU and I want to be able to do one-time purchases. And I want to be able to, you know, for the people who want subscription to be able to do that. So that totally makes sense. And then the other thing that you mentioned that was interesting was kind of like the, you know, the funny sort of brands that were like getting set up with you in the beginning. What was your first what was like the first brand you'd say you worked with where you're like, OK, this is this is the real deal. Like there's something like major here. And and what did that like transition look like going from like these kind of weird one offs were really willing to kind of take a flyer on you guys.

8:58Oisin O'Connor:And then you were like, wait a minute, like we actually got something. Yeah, totally. You know, it was interesting. So there's actually a funny story is, you know yeah we had a bunch of you know alternative different types of you know merchants early days uh with like kind of a niche and out there products but our very first company that actually ever installed us was a company called cachava and they had just started and today they're like a nine-figure business and so we got to see our very like row number one in our database is cachava and so to see them and partner with them over the last decade and see their huge success.

9:32That's been a huge, you know, driver for us because we just saw them. We're like, oh, wow, there's going to be a lot more companies like looking like them that will come on.

9:41Oisin O'Connor:Right. Yeah. And and I think that's like kind of the power of subscription. And we'll get into that in a little bit. But like, just for example, even like this brand, Olivia, that we're like bootstrapping and starting to scale up like for the first bit, you know, we were obviously with the first thing right out of the gates we did was not like set up subscription. We're worried about supply chain. We're worried about product. We're like at the Shopify store up, all of that sort of stuff. But subscription is so powerful as a compounding mechanism. Right. And, you know, we see it in the data. It was kind of like, you know, we'd be doing 3K, 4K, 5K a month, whatever, whatever, whatever.

10:16Oisin O'Connor:But then when we really turned on subscription, like all of a sudden you see the business just just start to like blow up. And like now, like 20, 30 percent month over month growth, it's like expected almost. It's wild what literally just flipping that switch can do to your business. Oh, 100%. And I feel like people don't start it quick enough, right? Because one, of course, this is like the simple math that we see across. We have like 30 ,000 merchants and we see that their one-time buyers are worth one-fourth of the value of their subscribers. So basically subscribers are worth four times more, which is crazy, right?

10:52So you should be doing everything to push people into subscriptions. But what's even crazier too is like, so we get a lot of like big brands that come to us and I had a big brand that came to us a couple of weeks ago and they had started this brand in the 2000s. So this is like super legacy. They actually did TV advertising to the brand, all that. And they had stopped advertising in like 2005. And the crazy thing is 15 % of the customers they acquired in 2000, they still have today. So you think about that. They were making money for two decades now on people they acquired 20 years ago. That's insane.

11:37Right? And just think about the profit margin because so much of what's broken in commerce is that you basically have to feed money into acquisition and that's where all your margin gets taken out of. So if you can build this compounding base right over a long period of time, it basically makes your business just so much more profitable and able to outcompete everyone else who's basically surviving day by day by the acquisition. Yeah.

12:03Oisin O'Connor:And I think this is a super important point. And it's something we talk a lot about on the pod. It was something, you know, I thought a lot about before launching this business. And even sometimes when people come to me, they're like, you know, when you're thinking about getting things set up, like, how do you think about building a business? And I'm like, look, there's like a lot of competition. Number one, like just as a framework that I like to think about, number one, obviously pick a problem that's something that like you want to solve, you want to work on, because it's no fun like working and grinding on a business that you like really couldn't care about.

12:31Oisin O'Connor:So like, let's assume that you've got table stakes in terms of like founder, like product or market sort of alignment. But after that, like, you really want to make sure, especially in the commerce space that like the unit economics work for what you're doing, and you can pair up your acquisition flywheel with the unit economics of your product. So that might mean, you know, what does subscription look like for your business? Is this a product that, you know, naturally works with a subscription versus something that doesn't? What's the form factor? Is it something that's like light, easy to store, easy to ship?

13:02Oisin O'Connor:Or is it something that's massive that you're going to have a little bit more trouble with, right? And when you think through that, it kind of, you know, it's like a good way of thinking through things. Because the reality is, when you're building out that growth motion, like you were saying, CACs have been going up and up and up on Facebook. The platform's stabilized. It's more predictable. But if you want to push and you want to scale a budget there, you need to be able to have that LTV or that customer lifetime value that can support that motion. And subscription, to your point earlier, you said that you get the 4X, the customer LTV for a subscriber than you would have for a one-time purchaser, well, that all of a sudden increases what you can spend to acquire that customer and how you can do it predictably, right?

13:49Oisin O'Connor:So I think, you know, when you're thinking about building a business, subscription fits really well into the tailwinds of this landscape as well from a business builder's point of view. Totally. Yeah. And, you know, actually, last year, we migrated over this company called Guthy Ranker. They were like kind of like old school DTC on TV advertising, right? So they did brands like Proactive back in the day. They sold that for a couple billion. So they've done multiple brands, huge GMV levels. And when you talk to them, because I'm a big fan of history because I think that kind of gives you ideas of what the future will look like.

14:29And when you talk to them about how TV advertising changed, especially direct-to-consumer TV advertising changed from the 80s to the 90s, they said in the 80s, it was a lot more types of businesses that could advertise on TV, right? Because the cost to the payback worked, right? But as the market matured, the types of businesses that could actually thrive started to narrow, right? And it started to narrow to companies that had a high LTV, right? And you can think about this today, just like objectively, if you ever watch TV, is like the types of companies that advertise, right? It's like CBG companies, it's car companies, it's insurance companies.

15:09It's actually quite narrow, alcohol companies. It's very narrow the type of companies that thrive. And I think we're starting to see this more and more on Facebook and Meta and Acquisition is that it's becoming so competitive that certain business models are just starting to outcompete everybody else. And it's going to narrow what type of business you should do. It doesn't mean you can't do a different type of business. You have to know that it's going to be harder with time. Right. And, you know, we see in our own data is our merchants are growing way faster than the rest of the Shopify base.

15:42You know, not only because of our partnership and us providing great solutions to them, but also just the category of subscriptions is a better category than most.

15:50Oisin O'Connor:Yeah, absolutely. And like we're saying, the unit economics of the businesses lend themselves to that sort of thing. they lend themselves to growth. So I'd love for you if you can just talk to me a little bit about, you know, what do the businesses that get subscription, right? Like, what, what do they do? You've seen all sorts of businesses on recharge by now, right? You've seen ones that, you know, have like amazing outcomes. You've seen ones that have like less than amazing outcomes. What are the characteristics of the businesses on recharge that, you know, do the best the subscription-based business, like what are they doing that, like what's core to their DNA that, you know, really helps unlock their growth?

16:29Yeah, totally. So I think first, like, I mean, this is pretty obvious, but it starts with product, right? How good is the product? What does the product solve? Does it solve a recurring need, right? If it doesn't have that, it's very hard for it to work, right? You know? So I think that'd be my first point is like, you actually have to think about how often do people want to consume this product, right? And if they want to consume it regularly. The next question is, is your product good enough to stay in their daily rotation? Right. And, you know, when I think about this is the shopper, you know, at the end of the day, buys a product oftentimes to solve a problem, especially in CPG.

17:06It's like, hey, I have gut issues, so I'm going to buy a probiotic. You know, I want to work on building muscle mass. I want to buy creatine. Right. And so that problem for the consumer doesn't change. Right. It often it stays there. The question is, can you sell into them and then stay with them? Right. So I think that's first, that's core. It's like, it has nothing to do with technology, has all to do with the product you sell. Then I think the second is people understanding the acquisition funnel, right? Are they actually optimizing for subscriptions and to keep people at, right? And I think like, you know, you were, you were saying, Hey, you know, you guys, you didn't start with subscriptions right away.

17:47You turn it on. It's like a no brainer now. Is it even that level? Like people have to get to, and then people have to get to the level of like, wait a minute, I make four times more for my subscribers than my one times. I should optimize every touch point from the product page to the cart, to the checkout, to the post checkout as a conversion funnel to push them in. And maybe, you know, maybe I lose five, 10 % of my conversions because of maddening friction. But the reality is I know that I'm converting X and R people who are four times more valuable. So it all pays off, right? So I think then they figure out the conversion funnel.

18:21Then after that, what I see is people, so you get product right, then you get acquisition right. Then you really got to get your analytics right of understanding what is the true value for these people, right? And once you can understand the true value and what that looks like, then you can pump more money into top of funnel acquisition, right? Right. Once you got that, then I would start to focus on retention. Right. How do you stop them from canceling? You know, that's either through cancellation flows, either through a great shopper experience, either through rewards, things like that set up as well.

18:57But that's kind of the cycle that I think of, you know, and the truly great ones can master it all.

19:01Oisin O'Connor:Yeah. And I think that's a great framework in terms of thinking about it. It's because like you don't need to do everything all at once. Like think about it in phases. And even like us, when we're getting set up on recharge, I told you. like first was like build a good product, figure out, make sure it sells, like make sure it's something that people want. And then we can start, we can add the subscription. And now we're actually in the phase of like starting to optimize for CRO. So that's kind of my next sort of point. You mentioned the conversion funnel. What does a conversion funnel look like for a really high performing brand?

19:32Oisin O'Connor:How do they think about building the funnel for subscribers to like, you know, get into that experience? What components of PDP, cart, like, how does it all play together from anywhere from the top of funnel to the place the experiences in the cart or the checkout to, you know, create a great conversion experience? Yeah, totally. And I think number one, the best people test, right? The best people try multiple different things, right? So it's not like one size fits all. I would say, first, the best ones I've go subscription by default, right? So that is the default. And I think you can even go to Amazon now.

20:09When you buy a lot of products that are like, you know, CVG products or things, cosmetics or beauty or whatever, there could be on subscription. It's subscription by default now for a lot of them, right? Because they know that defaults matter, right? People like have, if people have to think about going into something, they're way less likely to do it than, you know, already being in it. So I think that's first, subscription by default. Second, I think it's the offer, right? Is like what, you know, we all know this is like, hey, what is the great compelling offer why they should subscribe, right?

20:40You know, hey, is it like a special like one time discount versus one time? Is it they get all these benefits? You have to give the right offer, right? And test that offer. And then I think once people are in your funnel, then the cart, you know, it starts to become like, it all starts to become either upsells or cross sells, right? And that really depends on your products. So it's like if you got them subscribing, now do you try to upsell them to higher frequencies for bigger discounts, right? You know, basically or quantity breaks. Or do you want to cross out like, hey, you know, they're you know, they bought two pace.

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21:14Now I'm going to sell a floss on subscription into them, right? That's where the cart comes in. And then the checkout again, same thing, cross sells and upsells and post checkout as well. So I and what I see is people get more aggressive in the funnel. So you might start with a smaller offer on the product page. And then by the time it gets to post checkout, that's your most aggressive offer. Because that's when you're really trying to convert the last group that's holding out.

21:38Oisin O'Connor:Yeah. And it's cool to see that you start this sort of stuff. You start getting a motion that's sort of six. And then as you start to scale, like we're talking about on the acquisition side, you're like, wait a minute. I can actually, through these improvements that I'm doing on the CRO and the conversion and the cart and the subscription, all of a sudden I can really drive AOV, which gives me more money to pour into that top of funnel. So those first two parts of the entire customer sort of experience are sort of solved for. The next thing I want to talk about is it's because it is something you mentioned is, and this is a great thing also, like anytime we're, you know, talking to the recharge team, like, you know, you guys are always super helpful in terms of like pointing out like, hey, here are the benchmarks you want to be hitting.

22:25Oisin O'Connor:If you are in this category, here's the churn numbers you want to hit. Here's ways that you can reduce churn. So I want to think about, let's assume that we've got a brand spun up. We're starting to do well. We're starting to get subscribers. And then now we want to say, okay, let's make sure our numbers look healthy. What is what is healthy look like in terms of, you know, general benchmarks? I know it may vary across categories, but generally for a subscription brand, what's a healthy number that you like to see? And then, you know, what are some ways that brands that are successful at like reducing that churn element?

23:03Oisin O'Connor:How do they how do they tackle it? Yeah, totally. So I think, you know, if you want to be healthy, you want your second order to be 70 percent or above. right like that's the benchmark of in the second order really matters the most because that's the biggest delta of churn right the biggest group turns out in that one to two and i think you're also in this period where people have just tried out your product for the first time right let's say they try your olive oil supplements you need it's your job then to educate them and keep them in on the journey with you right so the first 30 days is really important from like the onboarding sequence of how do they feel connected to the brand?

23:44How do they feel educated around the problem space that you're going after, how your product solves it? And what is it like things like the benefits and usage and when should they see those things? Right. So I think that's, I really tell people focus on order one, order two. Right. And then you can order like order three should be like 45 % or plus, right. And onwards. But if you fix those, like the first, let's say a couple orders that has huge impacts because by then you have a group of people who like the product have been using it for a while and they'll stay with you at a high way higher clip than if you hadn't fixed those groups so that that's what i would go after first

24:19Oisin O'Connor:and then the other question i was going to say is how do you like how do the best brands who do this how do they tackle it right like do you what tools does recharge have in there to like you know kind of monitor it the and like you mentioned analytics are such a big piece so like how do the brands actually tackle this, assuming that, you know, okay, I see that my numbers are maybe a little bit below that 70 mark or that 45 mark after month two and three, I want to get in there. You know, do you guys integrate with other tools so that people can like, like a Klaviyo or something? Like, what is the, what does the picture look like to say, okay, now we want to take action here.

24:56Oisin O'Connor:How do we improve it? Yeah, totally. Totally. Yeah. And I think our goal is to be like the best partner to help you retain your customers, right? Fundamentally, Like that's our mission. And by doing that, we want to be that retention platform in a lot of ways with subscriptions at the core. And so for us, it's like one, we got to give you the analytics so that you have the data to understand like, oh, hey, here's my cohorts that I'm acquiring. Here's how they're, you know, churning out month one, month two, month three or between orders. Right. Two, once we give you the data and then we also give you the benchmarks to understand, OK, here's what your business, what's happening in your business.

25:32Here's what, you know, the industry looks like within your category, right? And we have 30 ,000 merchants, so we can give you a pretty clear view of that insight. We then give you the tools then to help retain, right? And so, like, the key tools are here is, like, things like cancellation prevention. So when people go to cancel, how do you deal with that, right? How do you use that as a push point to gather data, to educate the shopper, to potentially give offers? So the cancellation flows. things like the upcoming order emails, we actually launched those out so that they're the first class in the user experience for the shopper to manage subscriptions.

26:13We have a lot of people, you know, 90 % of our customers use other email solutions like Klaviyo for like more campaign-based things. But we see more and more people want to use our email pages because what happens is, let's say you email a customer about their upcoming order. You really want to make it so that it's easy for them to skip a date. or to change the product and not have to like log into a website to figure that out. Right. And so because it's congruent, it's in one place, we allow you to do that. Another thing that we allow you is rewards. Right. So another big tactic that people want to do is as people get to order two, three, four, how do you reward the person so they feel connected to the brand and they feel locked into the program?

26:55Right. So we also provide that loyalty suite as well.

26:58Oisin O'Connor:Yeah. And another Another cool one that, you know, we've had the pleasure of leveraging is the automate flow. So maybe you talk about that a little bit in terms of like, so I mean, at least on the logistics side, you know, when you're dealing with 3PL or something like that, maybe, you know, in our case, we've got a certain type that goes out in the first order of a subscription. And then afterwards, there's a second type. And if you don't have ways to, you know, make adjustments like that in an automated fashion your 3pl is going to get really mad at you so you just tell us a little bit about like the flows and the automated side of things that you guys are doing yeah totally so we yeah we have a whole automate product which is like basically like very much like shopify flows where it helps all the back-end processes of like swapping out products changing tags the stuff the nuts and bolts to make your subscription program work so that's also really important um and then One actually that I did mention that we're really excited about is that we've launched an AI concierge for shoppers.

27:59So the biggest issue that we see in retention is the end shopper has a hard time managing orders. And we can all think about this as a shopper ourselves is oftentimes the issue you subscribe to these physical products, you end up getting too much of the product or you get versions of the product you don't want. and then you get frustrated and you cancel, right? And we see this in the data is like people that log into the customer portal, over 40 % of them want to cancel. When they cancel, you know, two thirds say either it was, you know, basically they weren't on the right product or they had too much of that product.

28:34And so what we actually have launched out now is the AI concierge is as you buy the product and you subscribe, you get notifications via SMS and then you can chat with the SMS to manage everything, right? Which has been a game changer on not only retention of these cohorts for shoppers, but we've also seen like when we survey shoppers using this tool, 93 % of them say it's essential. Like they wouldn't order or manage subscriptions without that tool. Wow.

29:05Oisin O'Connor:So basically the way it works is you guys are integrating with the SMS. So like orders go out, it can SMS text the customer, And then you have an AI layer that's interfacing between Recharge and the actual subscriptions and behaviors that they have set up and the customer in a super easy to deal with way. If someone says, hey, I'm out of town for a week. Can you change my order? It'll be like, oh, cool. I bumped your order a week. Or you're like, hey, this flavor isn't working out. What are the flavors you got? It gives you recommendations and you can choose your recommendations. Like, cool, I've updated your upcoming order.

29:39Things like that.

29:40Oisin O'Connor:And this area is super. And this is what always gets me about like the e-commerce enablement system is like there's so many like customer touch points and they always like overlap. And you've got like this overlap between what's happening in subscription, what's happening in support, what's happening in conversion, what's happening at the Shopify level. Like it's also like intertwined, like in this example, right? Like, you know, so much of like CX, like when customers reach out, it's like, hey, can you update my subscription or hey, can you help me here? And then the customer support real person or agent has to go take action.

30:14Oisin O'Connor:But, you know, developing tools and giving the merchants the way that like they can, you know, the AI can handle this like that. You're saving so much time just by being able to to do something like that with the customer. Right. A hundred percent. Yeah. Yeah, so like definitely like, you know, we see it significantly drops the custom support tickets that merchants have. Right. So that's a cost and that's like time. Also, it just delights the end shopper. Right. And like, you know, when I talk about like, you know, these like when I see these like more legacy subscription companies that move to us is the fact that they still have these cohorts, you know, 15, 20 percent of people there.

30:51They're buying decades later. That is the true value of these subscription businesses. Right. And that's the true uncompetitive dynamic that they build up. And I think so many people in commerce are really short-sighted because they've been built on this model. Like, I do a Facebook ad. I make a sale. I make a bit of money. And they're thinking day-to-day, which they have to because they have a hard time to get cash flow and so competitive. But I really think that the businesses that I see are going to be truly great companies are thinking decades outwards of like, oh, cool, we're going to build up this brand.

31:29We're going to have all these subscribers. We're going to build a great, delightful experience where people just won't turn off them. And they'll be using this for decades. And we paid whatever,$50,$70 for acquisition up front. And we make everything else as gravy.

31:43Oisin O'Connor:Yeah. No, it's awesome. And then I think the other point there that's just so important is like, you know, customers or people like they don't really care about software, like even recharge. Like before it was like, oh, you've got a customer portal where they can go in and they can update their frequency. But like at the end of the day, like when a customer wants their thing updated, they just want it updated. They don't want to like they're like, oh, yes, you can have a support agent tell them, hey, go into your portal and do this. But if they get a text and they're like, yeah, update it, like they're happy.

32:11Oisin O'Connor:The brand's happy. Less work for everyone on both sides and better experience. Right. Yeah. And it's so funny. It's like, I think people in our industry need to think more about their own shopping experiences and what they like, you know, and geared towards that because it's like, it's that simple. It's like, we're the end consumer and we all get frustrated when things are hard to manage, right? Like I can tell you right now, if I'm on a subscription and they ship me a bunch of products I don't want, by order three, I'm like, forget this brand. I'm out. I'm done. You know, and maybe I'll come back to it at some point.

32:44But what happens is I then like rage quit. I go into the post number portal. I quit. And then I'm on my Instagram or TikTok and someone starts talking to me about the same product or same problem with a different product. And I buy from them. I'm like, oh, I'll try these guys out. Maybe the experience will be different. it. And yeah, it's just really interesting. It's like, I think the truly big, great companies on us really think about customer experience a lot. Maybe that's also something just at the core.

33:12Oisin O'Connor:Yeah. And when you think about customer experience, it's everything. It touches every platform. It's not just the product. It's also the email communication from the top of funnel stuff you might be doing from when you acquire them to like the email campaigns you might be running in something like Klaviyo to the experience. Like, you know, subscription is such an important experience because like there's everyone knows like there's nothing worse than dealing with a subscription that you don't want to be on that you're getting charged for right so like but that's part of the customer experience i think that's that's a that's that that's a super spot on take the next thing i want to ask about and just get some clarity on because like we're talking about it's like this landscape is so complex with all these different tools they all have functions that sort of overlap even in the subscription space right like you guys aren't the only player.

33:56Oisin O'Connor:You guys are scaled up. Congrats on hitting the 100 million subscriber and ARR milestone. That's amazing. But tell me a little bit about the subscription landscape. What is it that you guys do? Where are the other players? How do you guys see this landscape evolving? Yeah, totally. So I think, number one, we always want to be the best partner for brands and entrepreneurs and builders to scale, right? And to start and scale, really, right? And so I think part of that is we want to be the best on innovation and R &D because you need the best solution. But we also want to be the best in support and guidance.

34:33Right. And so I think when I think on those those pillars, right, of like innovation, support and guidance, I think from a innovation perspective, you know, the reality is we power 75 percent of all subscriptions on Shopify. And we're the one, you know, our next biggest competitor, we're probably 10x the size them. So we just pile more money into innovation and we're in it for the long run, right? We're, you know, we've been doing this for a decade. I love working with entrepreneurs and builders. I want to do it for decades forward. So we're in that long run part, long-term partner for people, right?

35:09So that's our goal. And then I think on the guidance side, because we have so much data and because we see so much, it's my belief that we can also then become the best partner in giving you guidance on what you should do because we just see everything, right? And then support, we have to be great support just like everybody else. So I'm always, I'm never like focused on competitors because I think you need to be focused on the problems of the brands and the merchants you serve, right? But I think competition helps you become stronger, right? Yeah.

35:41Oisin O'Connor:And it might push you in different ways and give you the nudges that, you know, this is something that the market wants. But like to your earlier point, I think that what you said about guidance, is like so important because a lot of times brands like you guys it's it's almost like you know like when you're operating you said you guys started almost like as a little agency well even when you're an agency versus one brand you're seeing like 10 brands and how those 10 brands are like doing things so you've got like more data points to operate versus one and you guys at recharge you scale you said you you're serving 30 000 brands across like 100 million subscriptions so you see it and like i think one of the cool parts like even when you know we'd chat with the team, they'd be like, hey, guys, here's the benchmarks.

36:20Oisin O'Connor:Like, here's a couple like quick wins that, you know, you guys obviously aren't doing. Just turn them on. And we'd turn them on. And all of a sudden, like revenue would go up. You know what I mean? So like just having that like data and perspective and confidence to be like, this is kind of what you need to do and this will help you and this is best practice. It goes a long way. Totally. Yeah. And I think and then we because we see everything that's happening, we're then able to innovate faster because we then take the best practices and we bring it into the product. You know, because and, you know, it's been interesting.

36:52I was looking at the data today of all the products that we've launched in the last year. The incremental lift on merchants has been over a billion dollars.

37:00Oisin O'Connor:That's insane. Right. But all those products at the core started with us seeing what our merchants were doing, what was working, what was not, and then bringing those into the product so that we can better help accelerate the ecosystem, right? And I think in a lot of ways, that's how we want to be the best partners. We want to be not only hands-on from support perspective, but also that guidance and then also that innovation and product. No, absolutely. And the other questions I have for you is like, where do you see this space evolving to? Like what's next for Recharge? You know, you talk about innovation, different products that like excite you solving these like customer points.

37:39Oisin O'Connor:Like where are we headed in subscription? like you know call it like the mvp like you said it was like oh someone just wanted to be able to differentiate between a one-time product and a subscription product and now you hit these complex like landers with all sorts of customizations and personalizations um where do you see subscription going and what's kind of like on your roadmap as you think about continuing to uh you know build in the space yeah totally so i think like first i look at where merchants are and where they're going right so that's like my first my north star is the brands right and the merchants.

38:13So I think right now, life is hard, right? Like everybody has a million things they got to figure out, a million different systems, you know, especially in our categories, a lot of people have to like not only get D2C right, they got to get Amazon right, they got to get retail right. So things are just really complex, right? And I think what we see is people want more of a partner in that journey, right? More from a hands-on perspective, from, you know, product innovation, all that stuff. And I think from ours, they don't want to partner just like, hey, can you handle my subscription billing? They fundamentally want a partner of like, hey, how do I retain customers?

38:53You know, how do I keep my customers in for the long run? And what can you do to solve that? Of course, subscription is at the core of that, but that's the relationship they want with us, right? And so then when I think about that is like from us is like, hey, what do we need to do from a, you know, our account managers and guidance perspective, just like hands on like people almost like giving them more services to help them and support to from the product is we've been bringing in more of the data. Right. So we brought in we have all your one time data and your subscription data. Our goal is to bring in more data to give you that full picture of what retention looks like.

39:30Right. So you can know what's going. and then we also want to bring in the tools that drive retention right so you know we've launched a suite of tools around how do you convert people into subscriptions from the product page the cart to the checkout to the post checkout so we want to help you better convert we also launched a bunch of tools on basically how do you retain people right which is like loyalty and churn tools and fail payments and all that stuff and then now i think with the concierge ai concierge how do you communicate to your subscribers to lock them in better, right?

40:01Oisin O'Connor:On that journey. So I think that's our goal is to be the retention platform. And there's many pillars that lead into that. Yeah. And it's so cool how you started as like the subscription platform and that's like your core thing. But at the end of the day, that's what you're serving is like retention, which drives growth. And it's like a key part of the business. So the last question I have for you is, you know, for founders, right, who might be like thinking about launching a brand, maybe they have a brand. Well, I actually have two questions. The first one is like, what is the biggest mistake that like founders or like brand operators typically make when it comes to subscriptions?

40:38Well, I think first is they don't get that product, right? So I think first, first focus on the product, right? That you're making. Do customers love it? All that. Is it a repeated formula? Then I think the first, after that, again, it's acquisition, right? How do you create the funnel to push people to subscriptions? And I actually think when it comes to acquisition, what people do is they over-discount for people to subscribe oftentimes. And they don't make subscription by default. Those are the two easiest things. And it's actually interesting. We look at the data. If you make subscription by default, it converts 3x more people into subscriptions.

41:18If you move from a 10 % discount to a 20 % discount, it only improves it by 2%. Wow.

41:24Oisin O'Connor:That's wild. I had no idea. Our products were 20 % for its subscription. I may have to test that. Yeah, what you've done is you now have given a 10 % discount margin to these people forever for the lifetime when you didn't have to do it. So, yeah, no, that's super fair. Yeah. And the second thing that I was going to ask that, like, kind of pairs up with with what we're just talking about or what kind of experiments, you know, if you had like a one or two sort of experiments that founders should be running or testing with recharge, like what would those be aside from like turning on subscriptions in the first place?

41:58Yeah, I mean, I think the experiments, I would be first, I would focus on top of funnel. I'd be like subscription by default. I would add upsells to subscription. You can use our car checkout, post checkout tool or another one for that. So that'd be my first, right? And then I would be looking at the data of what the retention is and lifetime value of that. I then would experiment on how to keep people in the program, right? Because like, you don't want to scale the thing up too quickly and have a leaky bucket. So then I would experiment with like, okay, cancellation prevention. When people go to cancel, how do I educate them about the product, right?

42:34And like tell those founder stories. I would also experiment with the first 30 days, how to educate the person as well.

42:40Oisin O'Connor:No, I love that. Super sound advice. Appreciate you coming on. And for anyone who's looking to learn more about yourself all along, I love the content that you've also been posting on LinkedIn. Like, where do we connect with you? Why don't you just shout out your socials and where people can find out more about you and recharge? Totally. So feel free to always hit me up on LinkedIn or X. So LinkedIn is just my name. Pretty unique. So and X, it's a O-I-S-I-N-O. I always have my DMs open. I always love to hear from entrepreneurs, builders, people, you know, scaling businesses. I also keep my Fridays open for just calls with merchants because that's like the lightblood of like why we exist and who we want to help and partner with.

43:27So always down to chat, always down to like give back to the community. And yeah, that's awesome.

43:33Oisin O'Connor:I love that. And even as just like a builder, like thinking about it, like keeping Fridays open and staying close to the customer. That's a great one. So appreciate the time. Cool. Awesome. Thanks so much. If you enjoyed the show, we'd love your support. A rating and review would go a long way as we continue to host the best builders in DTC and beyond. Follow and subscribe to the show and make sure to check out our show notes where you can find our socials and weekly newsletter. Visit us on DTCpod.com to join our founder community and access resources from every episode. We'll see you on the next pod.

From the publisher

Oisin O'Connor is the CEO and co-founder of Recharge, the leading subscription management platform powering 75% of all Shopify subscriptions. Under his leadership, Recharge has become a critical infrastructure partner for over 30,000 brands, reaching 100 million subscribers and $100 million ARR.

In this episode of DTC Pod, Oisin pulls back the curtain on what it really takes to win with subscriptions in today’s DTC landscape. He shares insider strategies for subscriber growth, optimizing retention, and leveraging Recharge’s newest AI-powered tools to minimize churn. Oisin also shares specific benchmarks every brand should measure, real-world examples of subscription funnels that convert, and actionable experiments operators can run to unlock long-term profitability and scale.

Episode brought to you by Stord

Interact with other DTC experts and access our monthly fireside chats with industry leaders on DTC Pod Slack.

On this episode of DTC Pod, we cover:
1. Evolution of subscriptions in physical product e-commerce
2. How to spot and create product-market fit 
3. Differentiators that set Recharge apart from early competitors
4. The compounding power of subscriptions for long-term growth
5. Unit economics, LTV vs CAC, and why retention is king
6. What best-in-class subscription brands do differently
7. Optimizing conversion funnels for subscriber growth
8. Subscription benchmarks: churn rates, retention, and second order metrics
9. Reducing churn with data, cancellation flows, loyalty, and rewards
10. Automations and integrating Recharge with supply chain and 3PL operations
11. Leveraging AI Concierge for customer retention and support
12. Evolving customer experience and the need for seamless subscription management
13. How Recharge guides merchants with data, support, and innovation
14. Experiments and mistakes founders make launching subscription brands

Timestamps
00:00 Oisin’s background, founding story, and early agency experiments
04:06 The rise of Shopify and the breakthrough with Recharge
05:19 The subscription model: initial skepticism and quirky early adopters
06:47 Technical challenges in enabling subscriptions on Shopify
09:00 First major subscription brand success story
10:15 Compounding growth through subscriptions
11:36 Legacy brands and decades-long customer retention
13:06 Building DTC businesses with sustainable unit economics
14:37 Lessons from TV advertising history and the narrowing of scalable models
16:29 Key traits of successful subscription businesses
17:09 Product, recurring need, and conversion strategy
18:27 Understanding subscriber value and optimizing acquisition
19:26 Retention: keeping customers post-acquisition  
19:52 High-performing brands and funnel design
20:05 Subscription by default, offers, upsells, and cross-sells
21:39 Conversion tactics from PDP to post-checkout
22:38 Benchmarks for healthy churn and retention
23:06 How top brands reduce churn and track performance
24:58 Recharge tools: analytics, cancellation flows, Klaviyo integration
26:41 Rewards and automations to boost retention
27:33 Automate flows for backend fulfillment and logistics
28:20 Launching AI SMS concierge for subscriber experience
29:40 Reducing customer service friction and delighting shoppers
32:15 Customer experience as a core differentiator
34:04 The competitive subscription landscape: Recharge’s position
35:41 Product innovation, support, and actionable guidance
37:16 Data-driven product innovation and merchant success
38:04 The future of subscription, retention, and platform innovation
40:38 Biggest mistakes founders make with subscriptions
41:58 Experiments founders should run with Recharge
42:58 Where to connect with Oisin for advice and mentorship

Show notes powered by Castmagic

Past guests & brands on DTC Pod include Gilt, PopSugar, Glossier, MadeIN, Prose, Bala, P.volve, Ritual, Bite, Oura, Levels, General Mills, Mid Day Squares, Prose, Arrae, Olipop, Ghia, Rosaluna, Form, Uncle Studios & many more.  

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• #184 Jake Karls, Midday Squares - Turning Your Brand Into The Influencer With Content

• #205 Kasey Stewart: Suckerz- - Powering Your Launch With 300 Million Organic Views

• #219 JT Barnett: The TikTok Masterclass For Brands

• #223 Lauren Kleinman: The PR & Affiliate Marketing Playbook

• ​​​​#243 Kian Golzari - Source & Develop Products Like The World's Best Brands

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DTCetc - all our favorite brands on the internet
Olivea - the extra virgin olive oil & hydroxytyrosol supplement
Castmagic - AI Workspace for Content

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Oisin O'Connor - Co-Founder and CEO of Recharge
Blaine Bolus - Co-Founder of Castmagic
Ramon Berrios - Co-Founder of Castmagic

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