Payments innovation often focuses on speed, convenience and technical capability, but customers tend to remember the moments when something goes wrong. Failed payments, refund problems, fraud disputes and delayed transactions can shape trust more than the payment itself, especially as AI begins to play a greater role in how people search, choose and buy.
Santosh ‘San’ Nakra-Shah, co-founder and managing partner of ChilliMint, believes payments businesses need to combine technical strength with clearer positioning, stronger storytelling and a deeper understanding of customer behaviour. The consultancy works with banks, fintechs, payment providers and merchants to help make complex propositions easier to understand and act on.
In this week’s Five Minutes With…, Fintechly speaks to Nakra-Shah about her career in payments, why AI could make brand trust more important, the industry’s focus on the “happy path” and the questions agentic AI will raise around consent, authentication, liability and accountability.
Can you tell us about yourself and what brought you to this point in your career?
I didn’t set out with a grand plan to build a career in payments. I joined Barclays at 18 and found my way into the industry from there. What kept me there was the opportunity to build things. I’ve always been drawn to transformation, innovation and launching new ideas. During my time at Barclays, I worked on everything from text message banking and prepaid products to early contactless initiatives, and I loved seeing ideas move from concept to something customers actually used.
After 10+ years at Barclays, and two years in the mobile industry, I co-founded ChilliMint. I kept seeing brilliant businesses building great products but struggling to explain why they mattered. The technology was strong, but the story wasn’t always clear. We launched ChilliMint to bridge that gap, combining payments expertise with strategy, marketing and storytelling. Nearly 16 years later, I’ve worked across the payments ecosystem with banks, fintechs, payment providers and organisations including Visa, helping businesses turn complex ideas into something customers can understand and act on.
Looking back, the common thread throughout my career has been quite simple – I enjoy solving problems, building things and helping people see the value in new ideas.
What problem or opportunity are you most focused on right now?
AI is dominating almost every business conversation right now, and rightly so.
But for me, the biggest opportunity isn’t simply adopting better AI tools. As content and design become easier to create, they’re also at risk of becoming increasingly generic. What matters now is how we use AI to create efficiency while doubling down on the things that make brands distinctive – creative thinking, strategic insight, storytelling and a deep understanding of customer behaviour. Because content is no longer scarce, trust and brand positioning have become the real differentiators.
We’re already seeing this happen in search. The game is shifting from trying to rank on Google to earning visibility in AI Overviews, ChatGPT and Perplexity. The brands that consistently get cited, referenced and trusted across the web will be the ones AI chooses to surface. AI will change how we create, but it will also place an even greater premium on originality, credibility and trust.
What do you think deserves more attention than it is getting in your part of the industry?
I think the industry spends too much time focusing on the “happy path” and not enough time preparing for the “unhappy path”. By happy path, I mean the ideal scenario where everything works exactly as intended. The payment goes through, the customer gets what they need and everyone moves on. But customers rarely judge businesses when everything goes right. They judge them when something goes wrong. A failed payment. A fraud dispute. A refund issue. A delayed transaction.
Those moments often have a greater impact on trust and loyalty than the payment itself. This becomes even more important as Agentic AI enters the payments ecosystem. As autonomous systems start making decisions and transacting on behalf of consumers, we’re creating entirely new versions of the unhappy path. What happens when an AI agent buys the wrong product or makes a payment that the customer disputes?
The industry is investing heavily in innovation, which is exciting, but I think we need to spend more time thinking about trust, accountability and resolution. The businesses that get this right won’t just build better products – they’ll build stronger customer relationships.
What do you think people still misunderstand about your part of the industry?
One of the biggest misconceptions about payments is that it’s a technology industry first and a people industry second. The reality is the opposite. I’ve seen organisations spend months, sometimes years, building sophisticated products and features, assuming the technology will speak for itself. But customers rarely care about the mechanics behind a payment. They care that it works. They care that it’s simple, secure and convenient.
That’s why some of the most successful innovations in payments aren’t necessarily the most technically complex. They’re the ones that remove friction and make life easier for the customer.
People also underestimate how much of modern life depends on payments infrastructure. Banking is about managing money. Payments is about moving it. It’s the invisible layer behind almost every transaction, whether you’re buying a coffee, receiving a salary or making an online purchase. When payments work well, nobody notices them. When they fail, everything stops. The companies that succeed are usually the ones that understand both sides of the equation: the complexity underneath and the human experience on top.
What do you expect to rise up the agenda over the next year?
Over the next year, I think we’ll see the conversation shift from AI as an information tool to AI as a decision-maker. Today, most AI applications help people find information, create content or answer questions. The next phase is Agentic AI, where systems don’t just advise users – they take action on their behalf.
That has huge implications for payments. We’re entering a world where AI agents could compare providers, renew subscriptions, book travel or make purchases without a human being involved in every step of the process. The opportunity is enormous, but it also raises some fundamental questions. How do we verify consent? How do we authenticate an AI agent? Who is liable if something goes wrong? And how do we maintain trust when decisions are increasingly being delegated to machines?
For years, the industry has focused on making payments faster and more seamless. The next chapter will be about making them trusted, transparent and accountable in an AI-driven world. The organisations that start solving those questions now will be the ones that shape the next generation of digital commerce.
