WithCoverage, the New York-based InsurTech company, has raised $42 million in a Series B led by Sequoia Capital and Khosla Ventures to scale an insurance brokerage model that removes commission-based incentives in favor of flat-fee, outcome-aligned pricing. The company’s differentiation lies in combining AI-driven policy audits with in-house insurance, legal, and risk expertise, allowing fast-growing businesses to surface coverage gaps, reduce overspending, and manage risk with enterprise-grade rigor typically unavailable to mid-market firms. The funding signals investor conviction that insurance broking, long structurally stagnant, can be disrupted by incentive realignment and workflow automation, positioning WithCoverage as a modern risk-management operating layer rather than a traditional intermediary.

WithCoverage Raises $42M to Disrupt Insurance Broking