Loyalty Happens When a Customer Feels Understood
The most successful brands use logic to enable magic: they use data, technology, and AI to understand context, anticipate needs, remove friction, and make better decisions. The goal is to create customer experiences that feel effortless, personal, and relevant, says Ilaria Buonpane, CMO at Wear That, Chalhoub Group.
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Customer loyalty has never been harder to earn.
Consumers today have more choices than ever, making it easier to switch brands based on price, convenience, or a better experience. While businesses continue investing heavily in loyalty programmes, AI-driven personalisation, and CDPs, many still struggle to build relationships that extend beyond transactions.
According to PwC’s survey, nearly 1 in 3 consumers say they would walk away from a brand after a single bad experience, highlighting how loyalty increasingly depends on consistently delivering relevance and trust rather than simply offering rewards.
For Ilaria Buonpane, Chief Marketing Officer at Wear That, Chalhoub Group, the challenge isn’t whether brands should invest in emotional connections or commercial performance. It’s how to combine both.
She believes the strongest brands use technology and AI to remove friction and understand customer context, while relying on human empathy to build lasting relationships that customers genuinely value.
In this interview, Buonpane discusses why traditional loyalty programmes are reaching their limits, how AI can strengthen emotional loyalty without replacing human interaction, why luxury brands still lead in customer relationships, and why modern CMOs are increasingly well-positioned to become future CEOs.
In modern loyalty systems, have brands become too obsessed with logic while underinvesting in the emotional side of customer relationships?
What I see today is a Growing Polarisation.
On one side, you have brands relentlessly optimising conversion, retention, frequency, and LTV. Their loyalty programs are beautifully engineered around company economics, but often disconnected from customer psychology.
On the other side, you have brands investing heavily in storytelling, community, and emotional connection, but without the commercial fundamentals to sustain it. They’re creating love, but not necessarily profitable growth.
Both models eventually hit a ceiling. What I’ve learned over the years is that loyalty lives at the intersection of logic and magic.
- If you focus only on the numbers, you can build an incredibly efficient business, but customers stay only as long as the economics make sense. The moment a better offer appears, they leave.
- If you focus only on the emotional side, you can create genuine affinity, but it becomes difficult to scale consistently and profitably.
The most successful brands use logic to enable magic: they use data, technology, and AI to understand context, anticipate needs, remove friction, and make better decisions.
The goal is to create experiences that feel effortless, personal, and relevant. Because knowing my name, birthday, and purchase history doesn’t create loyalty, but recognition. Loyalty happens when a customer feels understood.
Many loyalty programs today feel financially engineered rather than emotionally designed. How can brands realign what loyalty means to modern customers?
I think many loyalty programs are solving for the wrong outcome. Loyalty is still treated as something customers join: a card, a tier, a points balance, a separate destination.
But customers don’t wake up wanting to be loyal to a loyalty program. They want Convenience, Confidence, and Relevance. They want brands that make their lives easier.
That’s why I believe the future of loyalty will be largely invisible.
It won’t sit alongside the experience. It will be embedded into the product, the service, and the relationship itself. Over the next decade, the brands that grow the fastest won’t be the ones with the biggest loyalty programs. They’ll be the ones that make loyalty programs almost unnecessary.
Most brands are still asking: “How do we reward loyalty?” The next generation of brands will ask: “How do we earn loyalty every day?” That’s a fundamentally different mindset.
The winners won’t necessarily have the best points structure or the most sophisticated tier system. They’ll be the brands that become part of a customer’s routine, identity, and decision-making process.
AI will accelerate this dramatically. Not because it will send better offers, but because it will help brands understand context, anticipate needs, and show up at exactly the right moment.
Wear That combines human stylists, data, and technology. In your view, how can AI genuinely strengthen emotional loyalty, and what do you see as the new role of human interaction?
I think the conversation around AI is often framed incorrectly. The debate is usually whether AI will replace humans. Customers care far less about that than we do.
What customers ultimately want is confidence: confidence they’re making the right choice, confidence they’re not wasting time, confidence they’re not making a mistake.
The future belongs to whichever interaction, human or AI, creates the most confidence.
That’s exactly how we think about it at Wear That. When we launched Kendra, our AI stylist available on our app, the goal wasn’t to replace our stylists. It was to make personalised styling accessible at a scale that simply wasn’t possible before.
The real opportunity for AI is that it allows brands to move from reacting to customers to anticipating them. It can recognise patterns, remember preferences, and identify needs before they’re explicitly expressed.
When a brand consistently saves me time, reduces decision fatigue, or shows up with something genuinely relevant, I feel understood. And that’s a powerful driver of emotional loyalty.
At the same time, I believe AI will fundamentally change the role of human interaction. As AI becomes better at recommendations, information, and routine tasks, human interactions become more valuable, not less.
At Wear That, Kendra might know that you’ve bought linen dresses three summers in a row and are planning a beach holiday. A stylist understands that you’re feeling disconnected from your wardrobe and looking for confidence, not just clothes.
That’s the difference. AI helps customers feel known. Humans help customers feel understood. The brands that win won’t be the most automated. They’ll be the ones that use AI to create relevance at scale and reserve human interaction for the moments where empathy, judgment, and reassurance matter most.
You’ve led growth and CX transformations across sectors. Which one do you think understands emotional loyalty best today — and which still treats loyalty too mechanically?
Historically, luxury has understood emotional loyalty better than almost any industry. Luxury brands have always known that people don’t buy products alone. They buy identity, aspiration, confidence, belonging, and self-expression.
Whether you’re buying a handbag, a watch, or a dress, you’re often buying how you want to feel. That’s why luxury has been building emotional loyalty long before the term became fashionable.
On the other hand, many marketplace and subscription businesses have traditionally approached loyalty through economics: discounts, rewards, convenience, and switching costs.
Those levers absolutely work. The problem is they’re rarely defensible. Someone can almost always offer a bigger discount, a better reward, or a lower price. What’s interesting is that I think we’re now seeing a convergence.
The most exciting companies today are combining the efficiency and personalisation of technology with the emotional intelligence that luxury brands have mastered for decades.
Do you think CMOs have the right set of skills that make them poised to be good CEOs in a leadership shift?
I do, but only if we’re talking about modern CMOs, not traditional ones.
Historically, marketing was responsible for brand, communications, and campaigns. That’s not the role I’m seeing today.
The best CMOs now sit at the intersection of customer, product, technology, data, commercial performance, and growth. They’re often one of the few executives with visibility across the entire customer journey, from acquisition all the way to retention and advocacy. They can connect customer behaviour directly to business outcomes, and that’s incredibly valuable at the CEO level.
What makes modern CMOs particularly interesting CEO candidates is that they’ve spent years operating across functions rather than within them.
Growth doesn’t sit in marketing alone anymore. It sits at the intersection of product, technology, customer experience, operations, commercial strategy, and brand. And that’s exactly what CEOs do every day: align multiple functions around a common outcome.
That said, being a great CMO doesn’t automatically make someone a great CEO. The CMOs who make the transition successfully are the ones who complement customer and growth expertise with strong financial, operational, and organisational leadership capabilities.
But if you look at where business is heading, I think we’ll see many more CEOs come from marketing backgrounds over the next decade. Not because they’re marketers. But because they’ve learned how to translate customer insight, technology, and commercial performance into one coherent growth strategy.
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