
The Leadership in Insurance Podcast - Insurtech & Innovation ποΈ Josh Levine (Cake and Arrow) on Redesigning Insurance for Gen Z's Reality
Feb 2, 2026
42:48
In the latest episode, Alex sits down with Josh Levine, founder and CEO of Cake and Arrow, a design and product innovation firm specializing in the insurance industry. They explore what's really broken in insurance user experience - and how the industry can fix it.
Drawing on Cake and Arrow's own research into Gen Z attitudes, the conversation reveals critical insights for the industry's future.
Key Takeaways:
- Gen Z sees insurance as out of sync with reality β They still want stability, but view traditional paths as broken, leading them to create workarounds like emergency funds and side hustles rather than using conventional insurance products
- Internal UX is the new battleground β The focus has shifted from customer-facing platforms to redesigning critical internal tools like underwriting workbenches and agent portals, because better employee experience drives better customer outcomes
- Insurance has a perception problem with talent β Only 13% of Gen Z are in career roles within the industry, despite insurance offering faster career advancement than many realize
- AI is creating an opportunity β As AI reshapes employee experience, there's a chance to make insurance work more engaging and attract the next generation of talent through flexibility, dynamic career paths, and clearer purpose
A must-listen for anyone thinking about digital transformation, employee experience, or how to build products that meet people where they actually are.
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