WithCoverage

For most growing companies, buying insurance still looks the way it did decades ago: a broker, a stack of PDFs, a chain of emails, and a policy almost nobody reads closely. WithCoverage, a New York startup founded in 2023, was built on the premise that the broker at the center of that process is the problem - not because brokers are careless, but because of how they are paid.

Traditional brokers earn commissions from carriers, sometimes as high as 30% of a customer's premium. That structure quietly rewards higher prices and thicker policies, leaving many businesses in an odd position: overcharged and underinsured at the same time. WithCoverage's answer is to change the incentive. It charges clients a transparent flat fee and takes no commission, so the company only looks good when a customer pays less and is covered better.

To make that work at scale, WithCoverage pairs licensed insurance experts, attorneys and claims specialists with an AI audit engine. The software reads a business's existing policies and operations, flags the exposures a rushed human might miss, and produces a line-by-line breakdown of potential savings and risks - often on the first phone call. The human team then negotiates, running competitive bids across dozens of carriers.

The results the company reports are concrete. Hungryroot says it cut premiums 40%, more than $300,000. Bluestone Lane says it saved over $139,000. Tacombi describes WithCoverage as its "fractional Risk Management Team" and cites $200,000 a year in savings. Across its book, WithCoverage says it routinely saves clients more than $100,000 annually, with some trimming up to 30% of their total insurance budget.

In January 2026 the model drew a $42 million Series B, co-led by Sequoia Capital and Khosla Ventures, with participation from 8VC and Crystal Venture Partners. The company said the capital would fund product engineering, new industry verticals and more than 75 additional hires across product, business development and risk management.

The founders bring a track record of unbundling slow industries. JD Ross co-founded Opendoor and was an early employee at fintech Addepar; Max Brenner, the CEO, helped scale Compound past its first $1 billion in assets. Their shared bet is that risk management - not just insurance - is a category ready to be rebuilt around software and aligned incentives.

On one side are the incumbents - Marsh, Aon, Gallagher, Hub International - deep, established, and built on the commission model WithCoverage is trying to unwind. On the other are newer digital brokers such as Newfront, Vouch, Embroker and Founder Shield, which have modernized the buying experience but often keep the same underlying economics.

WithCoverage's wedge is the flat fee plus an AI audit that treats risk management as an ongoing service rather than a transaction. The company frames its ambition beyond insurance entirely: to modernize risk management across sectors, expanding from food and consumer into areas like construction and aerospace. Whether the flat-fee model scales across those verticals is the open question its Series B is meant to answer.