Why Financial Services Leaders Need Better Data, Not Bigger Promises – with Moshe Winegarten

“AI isn’t a magic bullet — it’s only as good as the data you feed it.” – Moshe Winegarten

If there’s one thing to take from this episode, it’s that successful AI adoption starts with good data, steady leadership, and a healthy dose of realism.

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💡 About the episode

AI might be everywhere right now — but in financial services, it’s been quietly shaping the industry for years.

In this episode, Kenny sits down with Moshe Winegarten, fintech and payments leader experience at Visa, Checkout.com, and Ecommpay, to unpack what real AI adoption looks like in one of the world’s most complex, data-heavy industries.

Moshe talks about the lessons from early machine learning systems in fraud detection, what’s changed in a decade of innovation, and why the biggest breakthroughs in AI often come down to something very old-fashioned: collaboration and discipline.

Here are some key takeaways from the conversation:

1. AI is only as strong as your foundations

Financial services run on data, but much of it is still messy, unstructured, and scattered. Moshe explains that the real challenge isn’t whether AI can analyze it, but whether the data is good enough to learn from in the first place.

“Garbage in, garbage out” still applies. Leaders need to invest in cleaning and structuring their data before chasing sophisticated models.

2. Adoption starts with people, not platforms‍

Too many organizations still try to roll out AI from the top down – hiring an “AI team” and expecting magic. Moshe argues for a co-development approach, where teams work together to identify pain points and test small, meaningful improvements. This creates ownership and reduces resistance.

3. Balance excitement with realism

‍Yes, the technology is improving fast. But rushing to scale untested systems can damage trust and morale. Moshe reminds leaders that AI transformation is a long-term investment; something you build in layers, not leaps. The goal isn’t to move first, it’s to move wisely.‍

4. Keep the human in the loop‍

In a sector defined by trust and regulation, the human element remains critical. AI can enhance decision-making, speed up processes, and improve experiences but people still provide the judgment, context, and empathy machines can’t.

“The best setup,” Moshe says, “is symbiotic – humans and technology working together.”

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Chapters

00:00 – Introduction to AI in financial services

02:30 – What fintech can learn from early AI experiments

05:15 – Real-world use cases in fraud detection and optimization

09:00 – Why data quality is the make-or-break factor

13:20 – Leading teams through change and managing expectations

18:00 – Avoiding the “move fast” trap

22:30 – Building a sustainable, human-centered AI culture

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About the guest

Moshe Winegarten is a fintech and payments executive with leadership experience at Visa, Checkout.com, and Ecommpay. He has spent over a decade helping financial institutions modernize through technology, focusing on AI-driven efficiency, fraud prevention, and customer experience. His approach to leadership blends pragmatism with curiosity — empowering teams to innovate responsibly and build lasting value.

About the show

The AI Opportunity is a podcast for business leaders who want to turn AI from noise into real results.

Each episode features someone who’s put AI to work inside real organisations and can show mid-sized companies (50–500 employees) how to start small, move fast, and scale safely.

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