WithCoverage

WithCoverage is a New York-based insurtech that replaces the traditional commission-based insurance broker with a flat-fee, AI-enabled risk management team. Its platform pairs licensed insurance experts, attorneys and claims specialists with an AI audit engine that scans policies and operations to find hidden exposures, run competitive carrier bidding, and cut premiums - routinely saving clients over $100,000 a year. Founded in 2023 by Opendoor co-founder JD Ross and Compound alumnus Max Brenner, the company has replaced brokers for 550+ fast-growing businesses including Gopuff, Bombas, Blank Street and Eight Sleep, and raised a $42M Series B in January 2026 co-led by Sequoia Capital and Khosla Ventures.