Insurtech WithCoverage has closed a $42 mn Series B financing round led by Sequoia Capital and Khosla Ventures, with participation from 8VC and Crystal Venture Partners.
The company was founded by JD Ross, co-founder of Opendoor, and Max Brenner. WithCoverage is reworking how scaling businesses assess, purchase, and manage insurance by combining AI-based analysis with in-house teams of insurance specialists and attorneys.
The goal is to identify exposures earlier, restructure coverage, and reduce total insurance spend without relying on commission-driven incentives.
Ross said the traditional brokerage model has barely changed in decades and remains misaligned with customer interests. Brokers earn more when premiums rise, which he described as a structural conflict.
WithCoverage was designed to operate on a flat-fee basis, removing commission incentives and tying value to outcomes rather than premium volume.
Insurance brokers have operated on the same commission model for decades – they get paid more when you pay more. We built WithCoverage to lead with our clients’ interests, not our own, and end that conflict of interestJD Ross, Co-founder of WithCoverage
WithCoverage begins each engagement with an AI-driven review of a company’s existing insurance and risk management program. The system analyses policies and operational data to surface coverage gaps, inefficiencies, and misaligned spending.
The internal team then designs a tailored risk strategy, runs a competitive carrier process, and manages the transition from start to finish.
According to the company, this approach frequently saves clients more than $100,000 per year while addressing risks that could otherwise result in significant losses.
WithCoverage says it has already replaced traditional brokers for more than 550 companies, including GoPuff, Blank Street, and Eight Sleep, and operates profitably.
Sequoia partner Roelof Botha said the insurance brokerage sector has long prioritised carrier relationships over the needs of insured businesses.
