Risk Team Director - Real Estate

WithCoverage • New York City, NY

8h • Onsite

About The Position

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 economy.

Requirements

• 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
• Deep technical command of real estate insurance programs, including Property (CAT-exposed and shared/layered towers), General Liability (habitational and commercial), Umbrella/Excess, Builders Risk, Environmental/Pollution, Workers Comp, Auto, and specialty lines (D&O, Crime, EPLI, Cyber)
• 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
• Strong analytical and strategic thinker, comfortable working across asset classes, geographies, and capital structures
• Builder's mindset, energized by the prospect of standing up a function from the ground up, codifying how the work gets done, and eventually hiring and leading the team that scales it
• Interest in mentorship and team leadership over time; prior people management is a plus but not required

Nice To Haves

• Designations (CPCU, ARM, CIC, CRM, CRIS) preferred but not required

Responsibilities

• Act as the senior technical lead on complex real estate placements, including layered/shared property towers, CAT-exposed portfolios, captive and alternative risk financing structures, wrap-ups (OCIP/CCIP), and lender/JV insurance compliance
• Design and refine client risk management programs tailored to real estate exposures across asset classes and lines of business (Property, GL, Umbrella/Excess, Builders Risk, Environmental, Workers Comp, Auto, Cyber, D&O, Crime, EPLI, etc.)
• Provide deep technical expertise on real estate–specific coverage issues, including CAT-exposed property placements, vacancy and protective safeguards provisions, ordinance & law, business income/rents, anti-concurrent causation, assault & battery sublimits, habitational liability, construction defect, and tenant/contractual risk transfer
• Partner with Risk Advisors on renewal and risk mitigation strategies, including SOV optimization, valuation accuracy, COPE data integrity, and modeling outputs (RMS/AIR) for CAT-exposed portfolios
• Lead loss analysis, benchmarking, and claims trend work across real estate portfolios to guide client decision-making and carrier negotiations
• Evaluate client operations, asset-level exposures, lease structures, vendor agreements, and contractual risk transfer mechanisms to propose proactive solutions
• Build the foundational playbooks, technical standards, and review processes that will define how WithCoverage delivers real estate risk advisory at scale
• Develop and deliver internal training on real estate exposures and emerging issues (climate, wildfire, convective storm, habitability litigation, AOB, social inflation), raising the technical fluency of the broader advisory team
• Serve as a trusted resource and mentor to Risk Advisors working on real estate accounts, with the expectation that you'll hire, build, and eventually lead a dedicated Real Estate Risk team as the practice grows
• Collaborate with leadership to shape the tools, technology, and processes that power real estate risk advisory delivery
• Engage directly with executive-level clients (CFOs, GCs, asset managers, principals) on high-stakes coverage strategy, program design, and carrier negotiations

Benefits

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
• Human Interest: 401(k) provider
• Time Off: Flexible time off, sick leave, family and medical leave, and major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed