In a move to overhaul the $500 billion insurance brokerage industry, New York-based startup WithCoverage has secured $42 million in Series B funding. The round was co-led by experienced investors Sequoia Capital and Khosla Ventures, marking the first collaboration between Sequoia’s Roelof Botha and Khosla’s Keith Rabois since their PayPal days.
Additional backing came from 8VC, Crystal Venture Partners, and Antifund, bringing the company’s total funding to an undisclosed amount beyond previous rounds.
My last company, Opendoor ($7B), replaced real estate brokers.
Today, my new company WithCoverage raised $42M to replace insurance brokers.
It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal. pic.twitter.com/Ps6Or1sIHI
— JD Ross (@justindross) January 13, 2026
Founded in 2023 by JD Ross, co-founder of real estate disruptor Opendoor (valued at $7 billion at its peak), and Max Brenner, a former founding team member at fintech firm Compound, WithCoverage aims to replace outdated insurance brokers with an AI-powered, flat-fee risk management platform.
Ross, who left Opendoor after scaling it to unicorn status, drew inspiration from his experience disrupting real estate agents.
“My last company replaced real estate brokers.”
Today, my new company WithCoverage raised $42M to replace insurance brokers,” Ross noted via X, highlighting the industry’s inefficiencies.
Traditional brokers often profit from commissions that incentivize higher premiums, handling hundreds of clients with generic advice via emails, PDFs, and spreadsheets.
WithCoverage flips this model by charging transparent flat fees, eliminating misaligned incentives.
The platform uses AI to scan policies for hidden traps, run competitive bidding wars among dozens of carriers, and provide expert-led risk audits.
This approach identifies coverage gaps, optimizes programs, and delivers savings—Hungryroot cut $300,000 annually, while Thirty Madison saved over $200,000.
The company’s AI engine, developed by teams blending product engineering with risk specialists, automates nuanced decisions to spot what human brokers miss. Customers receive line-by-line breakdowns of risks and savings on their first call, transforming a cumbersome process into a seamless digital experience.
With over 700 clients, including GoPuff, Eight Sleep, and Blank Street, WithCoverage has gained traction across sectors.
The fresh capital will fuel expansion into new verticals like construction and aerospace, product enhancements, and hiring over 75 employees in product engineering, business development, and risk management.
As fintech investor Nik Sharma, who seeded the company after discovering his own overpayments, noted:
“WithCoverage is going to do what Ramp did to banking and Shopify did to commerce.”
Reactions on X and LinkedIn have been positive, with entrepreneurs like Sarah Moret of Curie lauding the platform’s seamlessness after switching last year.
However, some industry voices, such as Sam Castronova, raised concerns about regulatory hurdles and limitations in high-risk sectors.
Despite this, WithCoverage’s mission to democratize comprehensive risk management signals a shift toward AI-driven transparency in insurance, potentially saving businesses millions while reducing vulnerabilities.
This funding underscores investor confidence in insurtech‘s ongoing evolution, positioning WithCoverage as a frontrunner in redefining risk for fast-growing companies.