Aug 20, 2026 · 26 min · 11 segments
Join us for another edition of Everything is Fintech, where host Oliver Smith sits down with Megan Caywood, CEO and founder of Caywood and former Chief Product Officer at Barclays, to explore the…
Megan CaywoodGuest
Oliver SmithHost
Oh, this is the perfect segue because I think where we are now, like within like a decade, we'll be regaling like, I don't know, whatever it is, Gen Alpha about what, you know, banking was like back in 2025.

Like, I think the next wave is we've had digital transformation over the past, you know, 20 years probably, but probably 10 years within finance.

And agentic AI are systems that don't just predict, but they act within regulated frameworks.

And what that means for the world of personal finance is that you're no longer going to have to worry about having a good user experience or a pretty dashboard or better insights because you'll be able to have a CFO in your pocket who acts effectively.

The intelligence that we can now bring into financial services is phenomenal.

That's where Scott Cook, the founder, started was with Quicken, like sitting at a dining room table with his wife, like with all these, you know, different bills and things everywhere.

And they both have like a Harvard MBA and they look at each other like, gosh, if it's this hard for us to manage our finances, how's the average American like, you know, doing on a daily basis with this stuff? It's complex.


But what we have now is whenever we have a new technology come to market, it shifts the art of the possible in terms of the experience.

But it's the way that they delivered it with new technology created a totally new experience and a totally new business model.

And my vision is that AI will create a totally new experience and a totally new business model for the world of finance.

And part of that is because at Starling and at Barclays, what we were trying to do is take everything that currently existed and just make it easier.

Just automate it as much as you can, take out as many steps as you can, just try to make it easy.

Oh, this is the perfect segue because I think where we are now, like within like a decade, we'll be regaling like, I don't know, whatever it is, Gen Alpha about what, you know, banking was like back in 2025.

Like, I think the next wave is we've had digital transformation over the past, you know, 20 years probably, but probably 10 years within finance.

And agentic AI are systems that don't just predict, but they act within regulated frameworks.

And what that means for the world of personal finance is that you're no longer going to have to worry about having a good user experience or a pretty dashboard or better insights because you'll be able to have a CFO in your pocket who acts effectively.

The intelligence that we can now bring into financial services is phenomenal.

That's where Scott Cook, the founder, started was with Quicken, like sitting at a dining room table with his wife, like with all these, you know, different bills and things everywhere.

And they both have like a Harvard MBA and they look at each other like, gosh, if it's this hard for us to manage our finances, how's the average American like, you know, doing on a daily basis with this stuff? It's complex.


But what we have now is whenever we have a new technology come to market, it shifts the art of the possible in terms of the experience.

But it's the way that they delivered it with new technology created a totally new experience and a totally new business model.

And my vision is that AI will create a totally new experience and a totally new business model for the world of finance.

And part of that is because at Starling and at Barclays, what we were trying to do is take everything that currently existed and just make it easier.

Just automate it as much as you can, take out as many steps as you can, just try to make it easy.
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