Joseph D'Souza started with a chatbot for stranded policyholders. The more valuable business was hiding behind the call center: helping insurance employees find the one trustworthy answer buried across PDFs, portals, inboxes, and shared drives.
Roojai began by making Thai car insurance easier to buy online. A decade later, it owns the underwriting stack, serves hundreds of thousands of customers and is testing whether a digital insurer can feel more human when the road gets messy.
Progressive became an insurance giant by doing something that sounds commercially reckless: making prices easier to compare. Behind Flo and the blue lettering sits a disciplined machine for pricing risk, distributing through both screens and independent agents, and turning insurance from a mystery into a shopping decision.