Risk Team Director - Real Estate

WithCoverage • New York, NY

1d • $200,000 - $250,000 • 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

• 8–12 years of experience in commercial insurance or risk management, with deep specialization in the Real Estate vertical, 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 technical understanding of real estate insurance programs, including Property (including 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
• Familiarity with CAT modeling outputs, COPE data quality, 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 (CFOs, GCs, asset managers, principals) in a clear, advisory tone
• Strong analytical and strategic thinker, comfortable working across asset classes, geographies, and capital structures
• Leadership mindset with a desire to mentor others and build scalable systems for growth within a specialized vertical

Nice To Haves

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

Responsibilities

• Directly responsible for client retention, client servicing, and oversight on new client placements across WithCoverage's Real Estate Risk Advisory Team
• Manage a growing team of Risk Advisors dedicated to the Real Estate vertical to ensure all conversion, execution, and servicing timelines are met
• Monitor and address performance metrics with the Real Estate Risk Team to ensure performance expectations are met across a rapidly growing book of habitational, commercial, mixed-use, industrial, and developer/owner-operator clients
• Maintain a culture of excellence across the Real Estate Risk Team as it pertains to day to day work, client engagement, and internal operational execution
• Lead the design and implementation of client risk management programs tailored to real estate exposures across multiple asset classes and lines of business (Property, GL, Umbrella/Excess, Builders Risk, Environmental, Workers Comp, Auto, Cyber, D&O, Crime, EPLI, etc.)
• Provide 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, wrap-ups (OCIP/CCIP), and tenant/contractual risk transfer
• Partner with Risk Advisors to deliver comprehensive renewal and risk mitigation strategies, including SOV optimization, valuation accuracy, COPE data integrity, and modeling outputs (RMS/AIR) for CAT-exposed portfolios
• Partner with Risk Advisors to oversee loss analysis, benchmarking, and claims trends across real estate portfolios to guide client decision-making and carrier negotiations
• Partner with Risk Advisors to evaluate client operations, asset-level exposures, lease structures, vendor agreements, and contractual risk transfer mechanisms to propose proactive solutions
• Serve as the senior technical authority on complex real estate placements, including layered/shared property towers, captive and alternative risk financing structures, and lender/JV insurance compliance
• Support internal education and development of best practices across the Real Estate Risk Team, including training on emerging exposures (climate, wildfire, convective storm, habitability litigation, AOB, social inflation)
• Collaborate with leadership to enhance processes, tools, and technology for real estate risk advisory delivery

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)
• 401(k) provider
• 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: Director
• Education Level: No Education Listed