Founded in New York, insurtech WithCoverage, an AI-enabled risk management platform positioning itself as a replacement for traditional insurance brokers for fast-growing companies, has closed a $42 mn Series B financing round.
The round was 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 interest
JD 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.
He said WithCoverage applies artificial intelligence to refocus the model around the customer, combining software with human expertise to modernise an industry that has resisted structural change.
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.
Roelof Botha, Partner at Sequoia Capital
“The industry also historically focused on carriers, and not the businesses seeking insurance. JD and Max have built a solution that puts the customer first,” said Roelof Botha.
“When we at Sequoia talked to the teams that use WithCoverage, we heard the same effusive customer love again and again. “The best claims call we’ve ever had.” “Your team will actually thank you.” “Instead of taking you golfing, they will actually save you money on insurance.” And then there were the bottom lines: saving customers up to 30% on their total insurance budget, representing up to seven figures.
The customers aren’t the only ones suddenly paying more attention to insurance. JD and Max understand that building applied AI is about capturing nuance – automating countless tiny decisions, in the right order, to deliver for their customers – and that is exactly how WorkCoverage operates.
Product and Engineering teams sit side-by-side with risk specialists, working together to design what customers truly need.
Beyond placement and negotiation, WithCoverage provides a dedicated platform for managing policies, certificates, claims, and renewals.
The system replaces email-driven workflows and spreadsheets with a centralised interface, giving clients continuous visibility into their risk profile and coverage status.
Keith Rabois, general partner at Khosla Ventures, said risk management remains more outdated than many other areas of financial services. He said the company applies technology, AI, and incentive alignment to a system that has relied on manual processes and legacy economics for decades.
The founders argue that while large enterprises employ internal risk managers, most businesses must rely on brokers whose scale-focused operations limit the depth of analysis they can provide.
WithCoverage’s AI audit engine allows for detailed, repeatable assessments that would traditionally be reserved for the largest companies.
The Series B capital will be used to expand product offerings and hire more than 75 employees across product engineering, business development, and risk management during 2026.
The company also plans to expand into additional verticals, including construction and aerospace, and is exploring opportunities beyond insurance in response to customer demand.
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.
Keith Rabois, General Partner at Khosla Ventures
WithCoverage positions its approach as a shift from insurance as a background cost of doing business to risk management as an active, continuously optimised function, supported by technology rather than driven by commissions.
WithCoverage is the modern Risk Management Team helping ambitious businesses replace their traditional insurance broker.
By combining advanced AI, industry-specialized experts, and a transparent flat fee model, WithCoverage delivers better protection, lower costs, and a radically improved insurance experience for high-growth companies.
