Fintech panels rarely deliver a number that makes the entire room stop scrolling. But at the Benzinga Fintech Day & Awards 2025 on Monday, Winston AI CTO Tomer Rosen dropped one that did exactly that: "More than 300,000 users were interacting with this feature" in just 90 days, referring to a personalized funnel built for Benzinga that turned casual website "tourists" into high-intent users.
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And while Rosen's case study anchored the shock factor, the broader panel made one thing clear: the future of retention is personalization, simplicity, and confidence-building — no matter which corner of fintech you operate in.
Winston AI: "If You Show Them That You Know Them, They Stay"
Rosen outlined the psychology behind the numbers: "If you show them that you know them… you don't overload them with a lot of information” and “it's like a relationship between two different persons… you want to leave a room for curiosity."
The result? A redesigned journey that made users feel seen, not sold to.
But Rosen wasn't the only one arguing that understanding the user beats overwhelming them.
eToro: Education + Empowerment = Confidence
Head of eToro Group's (NASDAQ:ETOR) U.S. operations, Andrew McCormick, echoed the same theme from a different angle: confidence is the unlock.
He reminded the room that "only like 21% of people ever sat on their home, their desktop computer, and opened an investing account."
So, eToro focuses on reducing fear — even if it means sweetening the deal a little. "Free money helps," he joked, describing their Learn & Earn quizzes. And the empowerment is real: "You can make a trade for as little as $10."
That simplicity mirrors Rosen's argument: reduce cognitive load, and users take the next step.
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Ramp: The Product Should Feel ‘Invisible'
Ramp's Andrey Kovalev took the idea a step further — not just simplifying actions, but eliminating them."We actually want to make it… fully automated” and “we want the product to feel invisible."
Kovalev frames retention as removing work, not adding features. If Rosen focuses on personalization and McCormick focuses on education, Ramp focuses on removing friction.
The Takeaway: Three Leaders, One Playbook
Across corporate cards, AI funnels, and retail investing, the message was nearly identical:
- Reduce friction (Ramp)
- Reduce fear (eToro)
- Reduce overwhelm (Winston AI)
- Increase relevance and simplicity (all three)
The 300,000-user proof point wasn't just Winston's win. It was evidence of a shift sweeping the fintech industry: Retention isn't about features. It's about feeling understood.
If you want to turn tourists into power users, don't build more buttons.
Build trust.
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Image created using artificial intelligence via Midjourney.
