Backed by Sequoia.
About the role
As Director, Real Estate Risk, you'll be WithCoverage's senior technical authority for risk advisory across our Real Estate vertical, supporting owners, operators, developers, REITs, syndicators, and institutional investors. You'll personally lead the most complex placements and serve as the in-house expert our advisors, service teams, and clients rely on for real estate–specific coverage strategy.
What they're looking for
- 10+ years of experience in commercial insurance or risk management, with deep specialization in the Real Estate vertical, ideally within a brokerage or consulting environment
- A senior individual contributor with a track record of personally owning complex real estate placements and being the go-to technical resource for advisors, clients, and carriers
- Demonstrated experience structuring programs for owner/operators, REITs, syndicators, developers, property management companies, and/or institutional real estate investors
- Working knowledge of lease and loan insurance requirements, waivers of subrogation, additional insured/AICOI compliance, and contractual risk transfer best practices for real estate
- Fluent with CAT modeling outputs, COPE data quality, and valuation methodologies, and how each drives carrier appetite and pricing
- Proven ability to communicate complex insurance and real estate risk concepts to executive-level clients in a clear, advisory tone
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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