Backed by Sequoia.
About the role
As the Director of Risk Management, you’ll lead our strategy and execution for client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. You’ll partner closely with advisors, service teams, and executive leadership to deliver world-class risk solutions that drive retention, growth, and operational excellence.
What they're looking for
- 8–12 years of experience in commercial insurance or risk management, ideally within a brokerage or consulting environment
- 2+ years of quota carrying-people management experience, ideally in a fast paced and high ownership environment
- Deep understanding of commercial lines (GL, Property, Auto, WC, Umbrella, and Specialty)
- Proven ability to communicate complex insurance concepts to executive-level clients in a clear, advisory tone
- Strong analytical and strategic thinker, comfortable working across clients and industries
- Leadership mindset with a desire to mentor others and build scalable systems for growth
More about this role
WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy.
We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed.
Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service.
WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $43M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners.
Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the...
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