Jerry.ai

Car and home ownership app

Jerry builds an AI-powered advisor that helps people manage the things they own, beginning with cars. It launched in 2019 as a car insurance broker and grew into one of the three largest in the country, then expanded into driving insights, vehicle diagnostics and a marketplace for repairs. The aim is to cover the whole ownership cycle in one app — shopping, insuring, maintaining, repairing and selling — and it is now extending that model to homes, motorcycles and RVs. Jerry serves more than five million customers and has been profitable since 2024. The company is remote-first, with offices in Palo Alto, New York City, Chicago and Toronto.