WithCoverage, a New York-based AI-enabled risk management and commercial insurtech platform, now protects more than $50 bn in revenue across over 1,000 businesses, according to the company. Clients include GoPuff, Eight Sleep and Blank Street.
The milestone follows rapid growth over the past 18 months. WithCoverage positions itself as an alternative to traditional insurance brokerage, combining AI-based policy analysis with in-house insurance specialists and attorneys.
The company was founded by JD Ross, co-founder of Opendoor, and Max Brenner. Its model is built around a flat-fee structure rather than broker commissions, with the founders arguing that commission-based compensation creates an incentive for brokers to earn more as client premiums increase.
WithCoverage starts engagements by reviewing a company’s existing insurance programme and operating information. Its technology examines policies for coverage gaps and areas of inefficient spending, while its internal team develops a risk plan and takes the programme to insurers.
The company also argues that traditional commercial insurance remains heavily dependent on PDFs, email and spreadsheets, with businesses often receiving only a limited number of quotes.
WithCoverage said its process puts multiple insurers into competition and reviews policy language alongside pricing before presenting options.
In January 2026, WithCoverage raised a $42 mn Series B led by Sequoia Capital and Khosla Ventures, with participation from 8VC and Crystal Venture Partners. The financing was intended to support expansion of its AI audit technology and insurance platform.
At the time of the Series B, the company said it had replaced traditional brokers for more than 550 businesses. Its latest figures put the client count above 1,000, meaning the customer base has nearly doubled since the beginning of the year.
WithCoverage said its approach frequently reduces annual insurance costs for clients while finding areas where existing coverage leaves businesses exposed.
Its website reports average savings of 20% to 40% for clients spending more than $1 mn a year on insurance and risk management services.
Ross has described the brokerage commission model as structurally misaligned with customers because broker compensation rises alongside insurance spending.
Insurance brokers have operated on the same commission model for decades – they get paid more when you pay more.
JD Ross
“We built WithCoverage to lead with our clients’ interests, not our own, and end that conflict of interest”, Ross stated.
