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.
Vivek Shah is the co-founder and CEO of SimplyInsured, a San Francisco company that lets small businesses compare and buy employee health insurance entirely online - billed as 'Kayak for health insurance.' An MIT-trained engineer and former McKinsey healthcare analyst, he started the company in 2012 after a maddening personal experience trying to buy coverage. Backed by Y Combinator (W13), Bessemer, and Polaris, SimplyInsured has served roughly 25,000 small businesses and saved them more than $50 million.