WithCoverage, an insurtech startup positioning itself as an alternative to traditional insurance brokers, said it has raised a $42 million Series B round led by Sequoia Capital and Khosla Ventures as it looks to scale an “AI-enabled Risk Management Team” for fast-growing businesses.
In a post on LinkedIn, co-founder and CEO Max Brenner said the new funding will support WithCoverage’s push to modernize the insurance brokerage process, which he described as overly reliant on manual workflows and misaligned incentives. Brenner argued that the commission-based broker model can encourage higher premiums and limit choices, while leaving businesses exposed to coverage gaps when brokers lack deep expertise in specific industries.
WithCoverage said its platform is designed to lower costs and improve protection by running competitive insurance shopping across a broad set of carriers, using a combination of AI and domain specialists to review policies for gaps, and handling execution tasks typically managed through back-and-forth emails and paperwork.
Brenner also highlighted early traction, saying that more than 700 companies have switched to WithCoverage in the last 18 months, including GoPuff, Eight Sleep, and Blank Street. He added that the company is expanding its team and hiring across multiple areas.
The CEO framed the raise as a milestone after what he described as a difficult entry into a highly regulated sector. He said he spent significant time meeting customers directly, including thousands of calls and travel across dozens of states, as he and co-founder JD Ross worked to build credibility with businesses evaluating a switch away from legacy brokerage relationships.
Alongside the funding announcement, WithCoverage promoted a free insurance analysis intended to show prospective customers potential overpayment and benchmark pricing typically accessed through brokers and carriers.
KEY QUOTES:
“Three years ago I made a gamble deciding to tackle such a regulated and deceptive industry.”
“So far it’s paying off. In 18 months, 700+ of the fastest growing companies like GoPuff, EightSleep, and Blank Street switched to us.”
Max Brenner, Co-Founder & CEO, WithCoverage
