Remember when companies like Kayak, Netflix and Amazon quickly upended the travel, entertainment and retail industries? They created streamlined, user-friendly online experiences and found ways to put customers in the driver’s seat. But traditional financial services—especially insurance—remain largely unchanged.

Meanwhile, American homeowners are grossly underinsured and natural disasters continue to strike. To better serve their clients, insurers need to consider modernizing coverage and updating rebuilding cost evaluations to meet consumer expectations....