🎙️ Josh Levine (Cake and Arrow) on Redesigning Insurance for Gen Z's Reality
Mon Feb 02 2026
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 – 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 productsInternal UX is the new battleground – 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 outcomesInsurance has a perception problem with talent – Only 13% of Gen Z are in career roles within the industry, despite insurance offering faster career advancement than many realizeAI is creating an opportunity – 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 purposeA must-listen for anyone thinking about digital transformation, employee experience, or how to build products that meet people where they actually are.
Hosted on Acast. See acast.com/privacy for more information.
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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 – 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 productsInternal UX is the new battleground – 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 outcomesInsurance has a perception problem with talent – Only 13% of Gen Z are in career roles within the industry, despite insurance offering faster career advancement than many realizeAI is creating an opportunity – 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 purposeA must-listen for anyone thinking about digital transformation, employee experience, or how to build products that meet people where they actually are. Hosted on Acast. See acast.com/privacy for more information.