🎤 AFTER DARK LIVE — CHICAGO • SEPT 17
Episode 418
September 5, 2025

The Sports Brand's Guide to Fandom

Klaviyo has become the de facto personal CRM for eCommerce. Ben Jackson, Managing Director for EMEA, joins us to unpack how brands move beyond campaign calendars into relationship-building at scale. We get into rocketship growth, why attribution is still broken, and how Castore’s multi-instance CRM model points to a future where both/and thinking beats false trade-offs.

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Klaviyo has become the de facto personal CRM for eCommerce. Ben Jackson, Managing Director for EMEA, joins us to unpack how brands move beyond campaign calendars into relationship-building at scale. We get into rocketship growth, why attribution is still broken, and how Castore’s multi-instance CRM model points to a future where both/and thinking beats false trade-offs.

If You’re Just Following the Data, You’re Following the Past

Key takeaways:

  • The marketer's identity crisis: Evolving from channel specialists to customer relationship managers orchestrating holistic experiences.
  • Scale meets personalization: Castore manages 32 Klaviyo instances while maintaining intimate relationships through strategic automation.
  • Attribution's cultural revolution: How brands are moving beyond "either/or" to "both/and" so they can measure immediate performance while building long-term value.
  • Channel affinity intelligence: AI identifies not just preferred channels, but optimal timing to eliminate fatigue.
  • "There's not many brands that you would get tattooed on yourself. But if you're a sports fan, if you're a supporter of a national team or a football club... that means you really care about the experience you have with that brand." - Ben Jackson on Castore's passionate customer base
  • "Rather than our reliance being quite heavy on sending out a load of email blasts to try and tick revenue targets... Let's tell those stories. Let's give the customer who we know is already incredibly passionate a reason to be loyal." - Max Holland (Castore) on content-driven relationship building
  • "If you're just following the data, you're following the past. If you're following the competition, you're following what everybody else has done, and it's really difficult to differentiate if you're gonna do that." - Ben Jackson on creative marketing philosophy
  • "Some of the impact you have as a marketer today, typically you take credit for the success in that moment. But some of it is about building that brand, building that customer experience... that doesn't just last for that point of one transaction. It kind of lasts over years." - Ben Jackson on long-term value thinking

In-Show Mentions:

  • Castore - Athletic wear brand managing 32 Klaviyo instances for partner teams and clubs
  • Rory Sutherland - Behavioral economist discussing explore/exploit marketing philosophy
  • K London - Klaviyo's European conference with 1,500 attendees and waiting list

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[00:00:05] Phillip: Ben Jackson, welcome.

[00:01:59] Ben Jackson: Thank you very much.

[00:02:00] Phillip: Thanks for having me. Yeah. It's a beautiful spot you've got here.

[00:02:04] Ben Jackson: Yeah, really nice, really nice. We moved in November of last year.

[00:02:08] Phillip: I was going to say, do you actually get to come to the office much?

[00:02:11] Ben Jackson: Yeah, when I'm in The UK. Three days a week when I'm in The UK.

[00:02:16] Phillip: Managing Director?

[00:02:17] Ben Jackson: Managing Director for EMEA. So that covers all of Europe, Middle East, and Africa.

[00:02:25] Phillip: Man.

[00:02:26] Ben Jackson: Got offices now, obviously, here in London, but we opened up an office in Dublin.

[00:02:31] Phillip: Which is growing by leaps and bounds, I hear.

[00:02:33] Ben Jackson: Oh, yeah. So we opened it in February. We have over 50 people in that office already. Twelve nationalities in that office.

[00:02:42] Phillip: Wow.

[00:02:43] Ben Jackson: Eight different languages, really diverse team.

[00:02:47] Phillip: Think of Steve. Steve Roland or...

[00:02:50] Ben Jackson: Steve Roland is there.

[00:02:52] Phillip: Steve told me he was said to be projecting in the hundreds in the next few months or something. I don't know. I don't know if that's public information. It just seems like Klaviyo is a rocket ship. And it seems like an incredible company to be with. Congrats on all of the success.

[00:03:08] Ben Jackson: Yeah, thank you very much. All driven by our customers, though, obviously. We're not just growing the number of employees, but we're growing the number of customers, growing in all of the different segments. We've even just opened up a well, we just hired a team in Paris as well. So we have two in that team already, but we're planning to grow that locally as well.

[00:03:31] Phillip: Obviously, all of this success is driven off of the back of your customers. It's an incredible time to be in ecommerce despite all the uncertainty. I'll apologize for some of the uncertainty in the world. {laughter} The United States certainly has its fair share in some of that. But despite all of it, it's kind of an amazing time to be in marketing, an incredible time to be driving marketing through platforms, especially those powered by AI. I was at K London. I saw you on stage.

[00:04:07] Ben Jackson: Thank you.

[00:04:07] Phillip: Some incredible announcements. We'll talk about that here in just a little bit. But a lot of those changes are driven by some really incredible shifts in perspective that I think you're at the forefront of here at Klaviyo. And one of those shifts in perspective was what I heard at your announcement of the B2C CRM back in February. For those who aren't familiar, give me a little bit about that shift of perspective about how the world is changing around this B2C CRM and the reorientation of the role of the marketer.

[00:04:41] Ben Jackson: Yeah, I think we're seeing that across the board. So not only in smaller organizations, but also larger organizations. The aspect of kind of thinking rather than "I'm a an email marketer," or "I'm an SMS marketer," so going from single kind of point of click kind of channels, more to a how do I manage the customer experience? How do I manage the customer relationship, not only from a single point of contact, throughout the journey of the customer.

[00:05:18] Phillip: So before I might have been a marketer where I'm thinking about marketing product. Now I've been in ecommerce for two decades. And I had the role of marketer and a strategist in former life. And I might have thought of myself as a person who, you know, I designed emails or I designed offers, I created Black Friday, Cyber Monday campaigns.

[00:05:43] Ben Jackson: Yeah.

[00:05:44] Phillip: What I heard back in February was there was a coming time where that might shift to someone who is more concerned about the customer relationship.

[00:05:51] Ben Jackson: Yeah.

[00:05:52] Phillip: That sounded like sort of pie in the sky vision.

[00:05:55] Ben Jackson: Yeah.

[00:05:56] Phillip: But I think you might actually be on to something.

[00:05:59] Ben Jackson: Yeah, yeah. So we launched the B2C CRM back in February. We're very excited about that. We have the vision that actually, it's about the customer experience across all of the different channels. And service is one of those, yeah. And increasingly, we're seeing the marketer care about what happens. And but typically, today, it's siloed. So there's a team looking after service, there's a team looking after marketing. There's data that serves the kind of service app, there's data that serves the marketing app, and they don't really mix that much. But actually from a consumer perspective, they don't know that. They expect the same experience across all of those different channels.

[00:06:46] Phillip: There is a brand that you use to sort of like the exemplar here at K London just a few days ago, Castore.

[00:06:55] Ben Jackson: Yeah.

[00:06:57] Phillip: I confess, I didn't know about the brand until a couple days ago. Now I see it everywhere. {laughter}

[00:07:01] Ben Jackson: {laughter} It's one of those brands that you don't know about, but you see...

[00:07:05] Phillip: Mirror exposure effect, right? And got to sit down with Max Holland, who is the Senior CRM manager over there. Incredible communicator, very passionate.

[00:07:17] Ben Jackson: Yeah.

[00:07:17] Phillip: He told the story on stage about how Castore is operating all of these instances of Klaviyo, not just for themselves and for their brands, but they're also operating Klaviyo on behalf of F1 teams on behalf of football and rugby clubs. They are growing and scaling not just technology for themselves, but for others. That is an important relationship, not just for their customers, but other brands are now trusting their customer relationships to Castore. {whoosh transition sound} As the Head and the Senior Leader at Castore and championing these CRM efforts, what are you doing right now in this world to make sure that every single touch point is personal for this very discerning customer?

[00:08:09] Max Holland: In a lot of cases, we manage the ecommerce and the marketing operations for a lot of our partner brands. The biggest challenge that we probably face is the sort of scalability of that. We have, speaking from a Klaviyo perspective, I believe 32 unique Klaviyo instances, each with their own set of templates and and flows, obviously, customer set that that sits behind that as well. So dealing with that level of scale while still trying to keep communications personal is a really difficult challenge. We're lucky that we have a really strong brand tone to speak to, whether we're speaking as Castore ourselves or whether we are essentially operating on behalf of a club store. A lot of the functionality that Klaviyo offers allows us to sort of build that personalized journey in a pretty scalable way by essentially cloning best in class from our other instances that we've seen work and perform and really easily, you know, flick that switch and and sort of have a almost an out of the box template that we're comfortable with that can serve our customer in the best way. {whoosh transition sound}

[00:09:15] Phillip: That to me exemplifies this idea of the shift of the idea of a marketer to a customer relationship manager. So when we were talking earlier, said it's like from outward focus to a customer, it's an internal focus. It's a reorientation. Talk me through that a bit. Talk me through the Castore...

[00:09:36] Ben Jackson: The Castore story is really interesting. I'll quote Max here as well. There's not many brands that you would get tattooed on yourself. But if you're a sports fan, if you're, you know, a supporter of a national team or a football club, to get that tattooed on yourself, you've gotta be really passionate about it. But that means you really care about the experience you have with that brand.

[00:10:01] Max Holland: {whoosh transition sound} I am a big sports fan. Anything that's on TV or on a field or a track or whatever, I'm certainly passionate about watching it. You're absolutely right. There are very few industries and sort of market sectors where that level of passion pervades everything that a customer does. Particularly where we're operating as on behalf of our partners across those sports, that passion gives us a license to speak to customers with that passion, but it's also a lot of trust that brands put in us to execute that in the right way as custodians of their brand, if you like, where they have that intensely passionate relationship with their customers. We have shifted the structure of our team to allow for specialization in the area of loyalty, in content creation, and in automation as well. So rather than our reliance being, you know, quite heavy on send out a load of email blasts to try and tick tick revenue targets and and and hit that box, we're in a really privileged position, as you say, where we have got these brands of which we are proud custodians and have a really rich story to tell and working with athletes and teams in order to do that. Let's tell those stories. Let's give the customer who we know is already incredibly passionate about the team, the people around it, providers that they use. Okay, let's leverage that content to drive customers to engage with us as a brand, understand us better, you know, leverage sign ups. So, from my perspective, my day to day is very much trying to shift away from a model of slightly reactive constant email builds to focus more on digital content creation, really giving customers a reason to be loyal and to sort of stay with our brand, almost replacing some of that reliance on bulk email sends with strategic automations that speak to the customer's journey. {whoosh transition sound}

[00:12:07] Ben Jackson: We started the relationship with Castore probably six years ago, maybe just over six years ago. And then as we've grown, and they were relatively small brand at the time, but we've grown with them, not only from a scale perspective. He talked about 32 different commerce stores that they've rolled out with Klaviyo, but also the different channels as well. So they started with us with the data platform and email, but have grown across all of the different channels as the consumer expectation of how they interact with them, although commerce stores has grown from a single channel to multiple channels. And they've been on our beta program for the WhatsApp and RCS launches that we did. They're part of the omnichannel beta program as well. So really exciting story, very close partnership throughout that six year journey.

[00:13:02] Phillip: That's a really good point to make, too, because this goes back to more of the programming from K Londan. This was part of the rewriting of the omnichannel promise. It's the continued evolution of not just launching the new B2C CRM back in February, but it's the launching of new channel support. So tell me a little bit more about the product evolution that was unveiled here at this event a couple days ago.

[00:13:33] Ben Jackson: Yeah. Well, the interesting stat that we learned through one of our surveys, 77% of consumers will interact over three or four different channels when they're interacting with a brand, when they're going to procure something. And we realized that really early on in our journey at Klaviyo. We also realized that really early on in our evolution in terms of the EMEA market. So about eighteen months ago, we did a lot of work in terms of localizing our product for the EMEA market, but also thinking about the delivery mechanism. So we now have 19 different countries that we deliver SMS to.

[00:14:17] Phillip: Wow.

[00:14:17] Ben Jackson: We were a database company, then we were an email company, then we're a cross channel company. And so we really need to take that communication to where the customer is or where the consumer is. And so in Europe, that's email, that's SMS, that's web, that's social. In some markets now, WhatsApp has been used a lot. For example, Germany is a big WhatsApp market, tends to be less SMS, more WhatsApp. RCS is a channel that I'm super excited about. And so it's all very well using all of those channels, but actually, you need to start understanding what the consumer prefers. Yeah? And at what stage in the journey does the consumer prefer to be communicated by each channel? And so that's why it's really important to bring it into one. I think we call it the omniverse.

[00:15:07] Phillip: Yeah.

[00:15:08] Ben Jackson: But if you think about omnichannel, it's then being able to use those different channels at different stages of the journey. And then if one doesn't work, then don't use it. Don't communicate with them because it might turn the consumer off.

[00:15:23] Phillip: One of the challenges with other product suites that I've seen is that you have lots of software with lots of channel support, and you also need lots of people to manage all of those channels at any given time. You wind up duplicating a lot of the same marketing messages across all of these channels and so you have a lot of fatigue and channel fatigue with a customer. You also don't know which channels are preference channels for a given customer at a given time. And so what you're saying is that there's a coming time or there is a time where Klaviyo can now find channels of preference for a customer and pilot messages to a given customer?

[00:17:07] Ben Jackson: Yeah, yeah. So I think the problem with the technology landscape, but also the way that brands have evolved as well, I think there's two aspects to that. We talk to a lot of customers and also prospects that over the years have been adding these different channels because they're not all especially new channels. But certain technology providers have provided the service over time. And so you come across these companies that have kind of gone out and bought what they thought was best of breed for each one of those different channels, which then means you've got different silos. You don't have a single place to run these campaigns out of.

[00:17:49] Phillip: Right.

[00:17:49] Ben Jackson: And then it's sometimes very hard to bring that back into your single source of truth. And so the technology becomes a barrier in terms of for the marketer, to really get that understanding of the customer. And so the way that we've built our platform is you have a single platform, a single data platform that allows you to drive into all of those channels. And then we've organically built each one of those capabilities on top of the platform. So it means you automatically get that in the same place. And as a marketer, you automatically have a single view of across all of those different channels. And then we already have the AI built into the platform. We also launched channel affinity as well. So you can really start to get an understanding of the attribution of your channels, but also the preference of the consumer as well.

[00:18:46] Phillip: Okay, so this was, to me, one of the most intriguing parts of the product announcement. It seems like there's some hint of a future where there's more of an analytics focus for Klaviyo. It looks like there's the ability to look at a more unopinionated way of attribution. There's now not just like last click attribution but like also multi touch attribution. A way of completely rethinking analytics but from within your marketing stack. Is this a hint of maybe what's to come in the future?

[00:19:29] Ben Jackson: Absolutely. As we build out more AI capabilities, you'll see more and more of that. You got to remember, we've got a lot access to a lot of data. And within our integrations with the other tools out there, like the commerce platforms, etcetera, etcetera, you're starting to see that come out in the functionality of the platform. And so there's more to come on this subject. It's a big focus of ours in Klaviyo.

[00:19:57] Phillip: What's really interesting in the demo, I'm gonna see if I can find a picture, I think I might have snapped a picture, but in the one example, was like you could almost go back in time and look at the efficacy of a campaign, like rework the numbers as if it were multi touch and reassess that campaign as if you had used a different attribution model. I don't know of another product that does that currently. That's pretty powerful.

[00:20:25] Ben Jackson: Yeah. And I think you're right, though, because not every organization wants to measure attribution in the same way. And so we recognize that over time.

[00:20:34] Phillip: Yeah. What are you hearing from customers in sort of their reception to this change in product? How are you adapting to their feedback? Where do you think that their adoption of the product is going?

[00:20:48] Ben Jackson: Yeah, so there's a couple of areas there I'll talk about. So the new channels, like RCS, WhatsApp, the reason why we run the beta is to get the customer feedback. And so the beta is not only them having access to the tool to play around with it, it's actually sending live campaigns out. And so that was an example of one of those beta customers that ran a WhatsApp campaign across the whole of Europe, and was super surprised about the success of results in all countries. And I talked a little bit about, you know, Germany being a WhatsApp country type of thing. What surprised me was actually it was across all countries in Europe that they saw that success. So that's the one area of the channels. We've also been beta testing RCS with our customers as well. In terms of the service area of the product, we launched into beta the customer hub. And we got over 1,000 customers already using that and implemented that on their sites. So we're all about running these tests with our customers to figure out how we can best develop the product going forward. But we are convinced that what we're doing is right. It's about refining what we do within each one of those channels.

[00:22:13] Phillip: Yeah. Just pivot a little bit. I got to spend some time with Rory Sutherland. And did you get to spend any time with Rory or Jamie Laing or or anyone?

[00:22:27] Ben Jackson: Yeah. Yeah. So I made sure I spent time with them before they did their talks. Rory Sutherland is just very insightful. Absolutely.

[00:22:37] Phillip: Legend.

[00:22:38] Ben Jackson: I intended to just talk to him for five minutes and ended up talking to him for half an hour, which I feel privileged actually.

[00:22:46] Phillip: Yeah.

[00:22:47] Ben Jackson: But I loved some of the stuff he was talking about. And I think it kind of like flows into what we're talking about at Klaviyo. I think the getting away from trying to measure things from a single point in time rather than looking at the lifetime value of a customer. And not just the lifetime value of the customer in three months, six months, but over years, I think is really interesting. Because some of the impact you have as a marketer today, typically, you kind of measure it, you take credit for the success in that moment. But some of it is about building that brand, building that customer experience. And that doesn't just last for that point of one transaction. It kind of lasts over years. And I love the way he talked about that. I also love the way he talked about the explore and exploit elements of marketing.

[00:23:47] Phillip: Yes. Yeah.

[00:23:48] Ben Jackson: The fact that if we're always using data to measure the marketing organization and never allowing them to experiment and come up with those really creative ideas that actually might be the big ideas that have the biggest impact. I love the way he talks about that.

[00:26:05] Phillip: There's a balance in, for a little bit of context, there's a balance between, and he gave a number of metaphors, right? So you had the sort of the bees the hive, right? You have those that go out and explore and you have the ones that are sort of the workers who are the almost the linear get the work done. And so what I really loved was his orientation towards our cultural behavior and our cultural acceptance. And that's something that we focus a lot on at Future Commerce is our cultural orientation towards and our cultural behaviors toward commerce. I thought it was interesting in his explore exploit visualization that a western mentality is an either/or proposition.

[00:27:57] Ben Jackson: Yeah.

[00:27:59] Phillip: I really recognize that in that we have really become, it's like it's either last click or it's multi touch. And it's either quarterly based growth goals or it's long term vision. And what he was proposing was that there's a fat tail philosophy, there's another way which is like, it's not either/or, it's both/and. This is another cultural orientation whereas that that's a very western mentality. In other cultures, there is no trade off. It can be both. And I think that that is such an interesting way to relook at the world. And in some ways, I see that in how you're rethinking the way the analytics works in the dashboard. In some ways, I'm starting to see that in the ways that our leaders in our leadership network at Future Commerce is looking at things and saying that we're not really trying to create campaigns that only return within this calendar year or in this fiscal. We're trying to think about things that are moonshots that will pay off outside of a window of attribution. So what are things that are immeasurable but are things that are coming from our intuition? And I think that that is a real break and departure in our industry. It gives me a lot of... It's exciting. And it gives me a lot of hope that we're having new conversations.

[00:29:32] Ben Jackson: Yeah. It's exciting for the creatives.

[00:29:34] Phillip: Really exciting for the creatives. Of which I'm one. So I can...

[00:29:37] Ben Jackson: And I actually, I went to the Jamie Laing fireside chat as well.

[00:29:42] Phillip: Yeah. Catch us up on that one.

[00:29:44] Ben Jackson: Yeah. I mean, just he's obviously a fascinating guy. Very charismatic.

[00:29:51] Phillip: Ultramarathoner, right?

[00:29:52] Ben Jackson: Yeah. Ultramarathoner.

[00:29:53] Phillip: Which I'm an ultramarathoner too.

[00:29:54] Ben Jackson: Oh, really? Wow. Wow.

[00:29:55] Phillip: He's very inspiring to me.

[00:29:56] Ben Jackson: But he did it with minimal training as well, which is...

[00:29:58] Phillip: Oh yeah. It's insane.

[00:30:00] Ben Jackson: Absolutely insane. I love that story. And I love the story about kind of how he got brought into kind of the Made in Chelsea program more because he wanted to launch his brand, his Candy Kittens brand, that he came up with at university with somebody that he knew. And I thought the kind of inspiring thing about that was he didn't try and copy anything. And this is kind of it. Rory and both Jamie kind of tied into the same message. It's about if you're just following the data, you're following the past. If you're following the competition, you're following what everybody else has done, and it's really difficult to differentiate if you're gonna do that. And so what he tried to do was something completely different in terms of he launched vegan candy. The packaging was completely different to everything you see in the shops as well. And I think that's inspiring. When you see ideas like that, it's inspiring.

[00:31:03] Phillip: Yeah. I was inspired by coming to K London. It was my first time coming. Incredible turnout.

[00:31:11] Ben Jackson: We were amazed, yeah. We launched the event, and we opened up the registration. And our head of marketing here kind of messaged me three or four hours after we opened it. It was like, "I'm so excited." We had three, four hundred people register in that first day.

[00:31:27] Phillip: I heard. I heard.

[00:31:29] Ben Jackson: And we had 1,500 registered for the day. We had a waitlist. We had people contacting us. Unfortunately, we couldn't fit everybody in. We originally had seats for 800. We managed to get them to extend it to 1,000, which is really exciting. I think it's a testament to the community that kind of has evolved. And that's not always driven by us trying to create the community. It's our champions, it's our partners, it's our customers. And then like, last night, when I got home, I was looking at kind of LinkedIn and all the messages from everybody that was there. It was inspiring.

[00:32:12] Phillip: And you should be. I covered the event just as, you know, as media. I spoke on stage with Joe McCarthy. We spoke about AI and some facets of sociology and the Dunbar number. I have a theory and a thesis that we're publishing some research on that we shared, which just to let you in on so you know what happened on your stage. But, you know, Robin Dunbar is a sociologist, anthropologist who proposed a theory about twenty five years ago, which was made popular by Malcolm Gladwell in his book Outliers, that human evolution has caused us in a tribal fashion to have upper bound and upper limit sociologically of about 150 maximum human relationships. Due to social media, we have way more contact with way more people than that at any given time and the theory so goes is that that's probably why we suffer so much mental stress. If we could manage relationships and those numbers of messages, we could probably do a little better to manage the stress in our lives. Our thesis and our research right now that we're working on is that it's not just human relationships. We also have brand relationships, and now we have emergent AI relationships that also vie for that 150. And not only do humans and brands all compete for those 150, but now chat GPT and Claude and Perplexity, those also count as 150 and those are all interesting. My small part of it, my LinkedIn was chock full yesterday and I think you all should be very, very proud of what you built. This community here seems very vibrant, very, very alive. And I think that it's a testament to this ecosystem.

[00:34:15] Ben Jackson: Yeah, thank you.

[00:34:16] Phillip: Can't say enough nice things.

[00:34:17] Ben Jackson: It was interesting. Yeah, obviously, the event was in London. But actually, the number of people that traveled into the event from all over Europe, which is really interesting. And, again, I think that's testament to partners, customers, champions, you know, we have really strong kind of champions within each one of those European markets. And that's really driving that community. So yeah, we're very happy with that.

[00:34:48] Phillip: Very good. What's next for you?

[00:34:50] Ben Jackson: Well, obviously, we're going through the launches of these new products. We're excited to get past the beta and actually see us go live and see the impact of what we have. I mentioned launching the office in Dublin, launching the team in Paris, we're launching the team in Germany. So, it's expanding our reach across all of those geographies, serving our customers locally, which is really important. So it's kind of taking what we've already built as the foundation and rolling out across the whole of EMEA.

[00:35:29] Phillip: Well, congrats on all the success.

[00:35:30] Ben Jackson: Thank you very much.

[00:35:31] Phillip: Thanks for having me.

[00:35:32] Ben Jackson: Thanks for coming in.

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