How Windsor Is Preparing for AI to Change eCommerce

Liam:

Freya, incredibly excited for today’s episode. Windsor is part of Shopify’s top 400 brands list in the US, which is an incredible company to be a part of. But you’ve had an incredible story and career before that as well. Why don’t you give everyone just a quick 60 seconds on who you are?

Freya:

Thanks for having me, Liam. I’m Freya, currently Senior Director of Ecommerce at Windsor Fashion. Before Windsor I was leading ecommerce and digital marketing at United Nude, an LA-based shoe brand. And prior to that I was living in Berlin, working at Zalando — Europe’s biggest fashion ecommerce platform, operating across all of Europe’s markets and doing about $13 billion annually.

Liam:

You actually started your career in customer data, which is very different to marketing. Why the shift?

Freya:

I really love consumer behavior — understanding the customer and how and why they do what they do. So I started in market research and customer analytics, thinking that’s where I wanted to be, close to that data. But once I was in it, I realized it’s really fun to gather data, but more fun to analyze it and be on the other end of it. I wasn’t really able to do anything with it, and I really wanted to build it into a strategy and see the results of execution. That’s how I ended up in ecommerce — the data would go into an abyss, handed over to brand teams who sometimes wouldn’t use it, and there was so much value sitting there. I was eager to get on the other side.

Liam:

Tell us about your time at Zalando. You ran some pretty epic campaigns there.

Freya:

I absolutely loved working there. It’s a fascinating company — a fashion company but tech-first, and I think that’s what really made the difference. I started the content marketing team there. At the time, content marketing was a big buzzword but no one really knew what it was. I had a team of four and after two and a half years had a team of 18. We were doing all of the content across the entire Zalando customer journey in all the countries — at that time 18 countries, across women’s, men’s, beauty, kids, sports, and luxury. So creating very different content for very different audiences. We were able to scale from a small team to such a large one because we weren’t just doing content for the customer experience online — we were creating content for all of the digital channels and touch points across the business. Homepage campaigns, collections pages, PDP copy, shooting PDPs, launching products, email content, paid content, and later working with the media services team selling placements on the site to brands.

Liam:

Was there a particular initiative that really stood out?

Freya:

Not a specific campaign, but as we kept growing we took on strategic initiatives like sustainability and streetwear. Those became a big part of the business. The question became — how do we communicate sustainability across the website? We’re buying sustainable products, it’s our job to sell them. How do we take what the customer wants to see and hear and experience when shopping sustainability, and launch that across all digital touchpoints? It was exciting to launch a whole new category — sustainability, luxury, streetwear, these big ideas.

Liam:

How did you get the team focused on those bigger strategic initiatives rather than just churning out content?

Freya:

Definitely a company-wide effort, and it has to be in the DNA. But we also had to take a step back and ask — what do we need to learn internally and externally to actually create content that has high click-through, that’s engaging, that converts? We interviewed the product teams — what’s important about this product, what’s different, what’s interesting to communicate to the customer? Then we did focus groups with customers — how do you want to experience sustainability, how can we communicate this to you in a trustworthy way? Then we met with our creative teams, did a deep dive, and came up with a strategy. It was really methodical.

Liam:

What’s your framework for getting people to actually engage with content?

Freya:

I think it’s twofold. Really understanding what’s the differentiator of the product and how can we tell that story through content? And then what’s authentic and what’s aspirational to the customer? I think good content has three layers — not within one piece of content, but across your experience and journey. That’s aspirational content, product-led content, and then personalization. If you can nail all three, you have a pretty good content strategy.

Liam:

Storytelling is something you’re super passionate about. Talk to us about that.

Freya:

It’s really hard to engage a customer these days because no one has time and they’re so distracted by devices and the competition they could be shopping with instead. Working for Windsor — we’re 89 years old. There are not a lot of trend fashion brands out there that are 89 years old. So we’ve had to rebrand and tell a new story very frequently. Storytelling plays a key role in that — being able to tell your brand story, tell a new story, and show up for the customer in the right way at that moment.

Liam:

Are there any brands outside Windsor that you look up to?

Freya:

For various reasons. Net-A-Porter — I’m always visiting their site to understand what their stories are and what their content looks like. They do an amazing job of sucking me into a world I want to be in but maybe can’t afford. And then Sephora is amazing in how they execute loyalty and customer retention. They have a best-in-class loyalty program that keeps me and a lot of other people coming back and only purchasing from them. It’s gamified — you want to know how many points you have, you desperately want to keep your Rouge status. Every time you walk into a store they acknowledge your spend and that you’re a Rouge customer. There’s clienteling, there’s gamification on their app. It really works.

Liam:

Is that storytelling, tech stack, and loyalty a big piece of why Windsor has been standing out in such a competitive space?

Freya:

Yes, I think so. We’ve really understood our customer in a way we haven’t before. We know where Gen Z lives and what she’s doing, and we make sure we have her back — which is one of our taglines this year — in every situation. We launched our mobile app about a year and a half ago, and that has really skyrocketed things in terms of retention, AOV, and getting the customer to shop with us more frequently. It’s also helped accelerate our strategy of moving away from being a milestone-focused brand that only speaks about prom or homecoming, to also speaking about everyday fashion. The app has accelerated that through storytelling and retention.

Liam:

How did you get the app going?

Freya:

We used Tapcart, and they’ve been a great partner — very easy to work with. We’re scaling slowly on the app, but we have the luxury of knowing our most loyal customers are there. We use the app almost as a testing ground — we’re much quicker to add integrations there to test new technology and get instantaneous feedback. Once we’ve gotten the app to exactly where we want it, we’ll also leverage our network of 350 stores. Right now we’ve grown the app digitally, but we’re going to be relaunching it in-store too, which will obviously show huge growth in downloads.

Liam:

You’re doing a PhD in AI, which is pretty exciting. Give us a brief on what you’re working on.

Freya:

I’m about halfway through my four-year PhD journey. I’m working on generative AI specifically — looking at how engagement changes across social media with the introduction of generative AI. I think this is going to become even more important as AI labeling becomes mandatory in the future, not just on social but across all digital channels. So far we’ve done a couple of experiments to understand that when content is labeled as AI-generated versus human-generated, you do see a significant drop in engagement. That drop is more significant in emotionally driven content versus more rational or information-driven content. But you can mitigate it with disclosure timing — if you disclose the use of AI later in the journey, you see less of a decrease. And I’m currently testing whether personalization can also mitigate that engagement drop.

Liam:

Do you think personalization will drive engagement back up, or do people find it creepy?

Freya:

I think it depends — it’s going to be very audience-based. And it depends on who’s doing it. I think it’s more creepy coming from a brand than from an influencer, for example. That’s something to be tested as well.

Liam:

As social platforms start labeling AI-generated content, do you think it’s actually the most important time for brands to be leaning into AI, or to stay human?

Freya:

It’ll definitely impact engagement and conversion. I think it’s about finding the right balance of AI versus human-generated content for your brand. At Windsor we use AI across various tools and touchpoints, but we’re careful. PDP copy is fine — we’re not impacting conversion. AI PDP videos work because they’re based on PDP images that were created by a human. There still needs to be that element of human emotion, and you build on that with AI.

Liam:

What’s one really safe AI use case every brand should just be using today?

Freya:

PDP copy just makes complete sense. And personalization across recommendations, merchandising, and search across your site — that’s an easy one. Customer service too.

Liam:

How is Windsor using personalization and what’s actually working?

Freya:

Personalization across our merchandising really works. We drop 200 products a week, so it’s hard to manage a big assortment while still putting bestsellers and new styles to the forefront. Personalization is where we see the revenue come in and the conversion happen — in our merchandising, our recommendation carousels, and recommendations in emails. Where we’re continuing to evolve is virtual try-on, which is coming next in our app. And interactive styling — almost like playing a game and styling yourself, which will let us show a lot more of our assortment and make the app more engaging.

Liam:

How do you decide what new tech to use?

Freya:

We have a clear roadmap with objectives around where we’re trying to grow — whether that’s conversion rate, AOV, or our international business. New tools have to layer into that strategy. But I also look at what other business units are trying to achieve, because ecommerce can operate in a silo. For example, we have 350 stores and one of their challenges is long fitting room lines during prom and homecoming season. Understanding their problem got me thinking — how can I use their problem to our advantage? So now we’re integrating a waitlist functionality in our app. You download the app in store to sign up for the fitting room waitlist, which incrementally increases our downloads but also solves their business problem.

Liam:

How do you balance the in-store and online teams pulling in different directions?

Freya:

At the end of the day we’re all working for one company, but of course there’s tension. We solve some of their problems, and on the other end we have ship-from-store on our site — taking product from the stores, sending it to our ecommerce customer and picking up that revenue. It’s a balance, but it’s one company at the end of the day.

Liam:

How do you think about first purchase versus repeat purchase at Windsor?

Freya:

It’s not necessarily the case that the first purchase is unprofitable at Windsor, because there’s a lot of discovery through a milestone moment. A customer might come to us for prom, and that’s quite a big purchase — so it’s a profitable conversion for us. But then it’s about tracking her journey and lifecycle from there. We don’t want her to be just a prom customer. After she’s entered the Windsor universe, we need to give her the right product at the right time. After prom, she might be interested in a festival outfit, or a New Year’s Eve dress. We make sure we’re targeting her with the right product at every stage in her journey through email, SMS, and push — and when she buys a prom dress she’ll be targeted with an offer for tops and bottoms to keep her coming back for everyday fashion.

Liam:

How are you winning the awareness game with young people?

Freya:

We have a really robust affiliate and ambassador program — a lot of our brand fans become our affiliates and ambassadors. We also do a lot of offline events specifically on campuses for sororities. That’s actually a retention play too — the prom dress purchase often happens before the customer goes to college, and in college is where she needs sorority event outfits or going out outfits. There’s always something to attend in college. So we do offline activations across US campuses, bring influencers, host events in our stores. That brings our customer in and she becomes engaged in the Windsor universe.

Liam:

How do you think shopping will change for young people with AI?

Freya:

I think the way customers search, how we sell, and how we advertise is going to completely change. Shopping is going to become very to-the-point versus browsing. It won’t be a customer going to multiple different sites to find what she wants — she’s going to put in a prompt, say this is what I’m looking for, and find the best option. We need to make sure our products show up when she’s searching for a specific dress for a specific concert. We already hear Gen Z and Gen Alpha saying “let me ChatGPT it” versus “let me Google it.” So it’s only going to become more important.

Liam:

In a world of AI, what does a brand actually control?

Freya:

I think you still control your narrative. But you need to be really purposeful in what you put on your site — the content and the words you use. The LLMs are learning from somewhere, and that’s your site. I think the purpose of a site in the future won’t necessarily be where people shop — it’ll be where people engage, where people understand who the brand is, what they represent, and what stories they’re telling. The site will almost become like a big blog.

Liam:

Why do most brands treat content as a side project rather than a revenue driver?

Freya:

Because content is very hard to track performance of — it’s hard to see the ROI. Performance marketing, you can easily see the return. But without content you’re not filling the space. At Windsor, for example, it takes an incredible amount of content to fill an app and make it engaging. At Zalando we were very lucky to have a huge in-house dev team, and we were able to build dashboards to track the return on investment of our content. That’s how we were able to scale it — because we could see that return. But that was a build-versus-buy decision that not every company can make.

Liam:

How do you track content ROI at Windsor today?

Freya:

We use first-click attribution. If a customer comes through a specific campaign and then converts after entering through that campaign, that revenue is attributed to that click. It tells us the campaign was interesting, she liked the image and the topic. But then we also did a good job merchandising — the product was interesting and we converted her. It gives us the full picture versus just looking at click-through rate, which doesn’t tell us the rest of that journey.

Liam:

How are you keeping your team up to date with AI and fostering a culture of experimentation?

Freya:

That’s what’s comforting actually — we’re all in the same boat, we’re all learning as we go. Things are changing every minute. So I think it’s just talking to other brands, seeing what they’re doing, having those conversations and learning from each other. We also have a dedicated AI Manager role within our team — a person who is looking into AI developments, making sure our site is doing as much as possible to get ready for agentic commerce when that really takes off. They’re sharing knowledge across the business, attending events, gathering insights. Right now they’re updating our PDPs for LLM visibility, updating bottom-of-page copy with FAQs for greater LLM visibility, and looking at channels outside our site like Reddit and YouTube — being present in areas that have authority but where the voices aren’t coming from Windsor directly. Every channel where we can get authority that’s not a Windsor voice is something they’re actively working on. Answering comments on social, having influencers speak on our behalf. All of that.

Liam:

Freya, thanks so much for coming on today’s episode. Looking back on what you’ve achieved over the last two years is really just a preview of what’s ahead, particularly with AI. And excited for the PhD too.

Freya:

Thank you. It’s a fun time — a lot going on, but very exciting.

We cover:

How AI and LLMs are changing product discovery and online shopping

Why personalization is a key driver of conversion and revenue

The role of content and storytelling in modern ecommerce

What brands need to do now to prepare for the future of ecommerce

If you’re building or scaling an ecommerce brand, this conversation breaks down what’s changing and what actually matters going forward.

00:00 Intro

03:10 From data to execution: why analytics wasn’t enough  

05:00 Building a content engine across 18 markets  

07:20 What actually drives clicks and engagement  

08:00 Why storytelling matters more than ever  

10:14 How Windsor’s mobile app skyrocketed retention  

12:27 AI research: how generative AI impacts engagement  

14:51 Finding the balance between AI and human content  

15:51 Preparing for LLM-driven commerce  

17:37 Why personalization drives conversion and revenue  

19:08 Bridging ecommerce and retail  

25:06 Lifecycle marketing beyond prom shoppers  

28:11 How AI will change shopping behavior  

36:11 Building an AI-ready ecommerce team