New York-based InsurTech WithCoverage has raised $42m in a Series B funding round as it looks to challenge traditional, commission-based insurance brokerage models for fast-growing businesses.
The Series B round was led by Sequoia Capital and Khosla Ventures, with additional participation from 8VC and Crystal Venture Partners, according to Beinsure.
The funding will be used to expand WithCoverage’s product capabilities, grow its workforce, and support entry into new industry verticals.
Founded by JD Ross, co-founder of Opendoor, and Max Brenner, WithCoverage aims to change how scaling companies assess, purchase and manage insurance.
The platform combines AI-driven analysis with in-house teams of insurance specialists and legal professionals, allowing businesses to identify risk exposures earlier and optimise coverage structures.
The company’s model is built around a flat-fee pricing structure, removing commission-based incentives that have historically dominated insurance brokerage. By decoupling revenue from premium volume, WithCoverage ties its value proposition to measurable outcomes such as cost reduction and improved risk positioning.
WithCoverage begins each client engagement with an AI-powered audit of existing insurance programmes. The system analyses policy language and operational data to identify coverage gaps, inefficiencies and overspending. Internal teams then design a tailored risk strategy, manage a competitive carrier process and oversee implementation end to end.
According to the company, this approach can generate annual savings exceeding $100,000 for some clients, while also reducing exposure to uninsured or underinsured risks.
Beyond placement and negotiation, the platform provides tools for managing policies, certificates, claims and renewals through a centralised interface. This replaces email-driven workflows and spreadsheets, giving clients ongoing visibility into their risk profile and insurance coverage.
The insurance brokerage sector has long been characterised by commission-based economics and limited structural change. WithCoverage argues that while large enterprises can afford internal risk management teams, smaller and mid-sized businesses have traditionally lacked access to the same depth of analysis.
Sequoia Capital partner Roelof Botha said: “WithCoverage harnesses AI to augment human expertise, advancing the intersection of insurance and technology. The insurance brokerage industry has largely remained unchanged over the past few decades and now stands poised to benefit from advances in artificial intelligence.”
WithCoverage co-founder JD Ross said: “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 interest.”
Khosla Ventures general partner Keith Rabois said: “JD and I teamed up at Opendoor to take on one of the most entrenched industries in real estate. Risk management is even more outdated. Max and JD are applying software, AI, and proper incentive alignment to a system that has needed reinvention for decades.”
The new capital will support hiring more than 75 employees across product engineering, business development and risk management during 2026. WithCoverage also plans to expand into additional verticals, including construction and aerospace, while exploring opportunities beyond insurance in response to customer demand.
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