WithCoverage Raises $42M in Series B for AI Risk Management Platform

Insurance has always sold certainty while quietly billing confusion. A trillion-dollar industry powered by commissions fat enough to distort judgment, where growing companies overpay, under-understand, and pray the worst never happens. Hope is not a strategy, especially when your business is scaling faster than your broker replies to email.

WithCoverage walks into that mess with clarity and receipts. Founded July 2023, headquartered in New York, now operating across NYC, Austin, San Francisco, Chicago, Philadelphia, and Salt Lake City, the company just closed a $42M Series B. Co-led by Sequoia Capital and Keith Rabois, with continued conviction from 8VC and Crystal Venture Partners. That is not speculative capital. That is experienced money leaning forward.

The model is the message. WithCoverage rejects commission math and replaces it with flat fees. Incentives finally line up. The AI audit engine does the unglamorous work most brokers never touch, reading policies line by line, mapping real operational risk, flagging gaps, redundancies, and quiet landmines. The outcome is not theoretical. Customers are seeing $100K to $200K+ in annual savings, often 20 to 40% reductions, while ending up better covered. Fewer surprises, stronger protection, cleaner books.

Leadership explains the pace. Max Brenner, Co-Founder and CEO, helped scale Compound to its first $1B in AUM and understands how to industrialize trust in regulated markets. JD Ross, Co-Founder, helped build Opendoor alongside Keith Rabois and learned how to dismantle entrenched intermediaries without breaking the customer experience. That pairing does not romanticize disruption. It operationalizes it.

The execution backs it up. 10x growth year over year while staying cash-flow positive. Hundreds of customers across manufacturing, defense, hospitality, consumer brands, construction, and aerospace. Real claims advocacy led by Phil Wilusz. Real risk leadership from Myles Hilliard. Growth driven by Rohan Taneja. Product and operations under Mitch Reinig. Engineering led by Cole Striler. Talent scaling under Jerico Brewer. Licensed, compliant, and built for adults in the room.

This raise is not about celebration. It is about pressure. Pressure on an industry that has hidden behind opacity for decades, and pressure on every founder who knows their insurance spend feels wrong but never had proof. WithCoverage does not sell peace of mind. It delivers evidence, and evidence has a way of changing behavior.