With Coverage

I take the side of people who build. Started WithCoverage, an applied AI lab modernizing risk & insurance. Co-founded Opendoor $OPEN

WithCoverage is a New York based insurtech that replaces traditional commercial insurance brokers with a hybrid team of human risk advisors, attorneys, and claims specialists working alongside AI agents. It targets fast growing companies with meaningful insurance spend, the kind of businesses that outgrow generalist brokers but still get pushed into off the shelf policies. Co-founders JD Ross and Max Brenner are pairing industry experts with technology , with Ross previously co-founding Opendoor and Brenner having built Compound into a multi-billion-dollar investment advisory platform after starting his career at Bain . This launch introduces WithCoverage 2.0, positioned as an AI risk management team rather than a chatbot bolted onto a brokerage. The platform runs specialized agents against a client's book of business, a policy agent that reads coverage documents line by line, a claims agent that reviews prior incidents and losses, and a benchmark agent that compares pricing and terms against similar companies. Human experts then use those findings to rewrite exclusions, close coverage gaps, and put roughly 40 A-rated carriers into competition on renewal, all billed on a flat fee instead of the commission model that rewards brokers when premiums rise. The timing follows a $42 million Series B co-led by Sequoia Capital and Khosla Ventures, with participation from 8VC, Crystal Venture Partners, and Antifund , and comes as WithCoverage says it now protects more than $50 billion in annual revenue across over a thousand customers including Opendoor, GoPuff, and Polymarket. For founders and operators, the pitch is a single system of record for policies, claims, COIs, and renewals, run by a team that specializes in their industry rather than a broker juggling unrelated books.

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