Risk Team Director - Real Estate

Risk Team Director - Real Estate 

Location: New York, NY

About WithCoverage:

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.

Why Join Us:

• Grow Faster – We’re scaling quickly, giving you significant opportunities to learn, lead, and shape your career and the company's future.
• Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
• Redefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.
• Financial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth.

About The Role:

As the Real Estate Risk Team Director, you'll lead WithCoverage's strategy and execution for risk advisory across our Real Estate vertical, helping owners, operators, developers, and investors understand, mitigate, and transfer risk across their portfolios. You'll partner closely with advisors, service teams, and executive leadership to deliver world-class, industry-specialized risk solutions that drive retention, growth, and operational excellence within one of the most complex and exposure-heavy verticals in commercial insurance.

What You’ll Do:

•  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

Who You Are:

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

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $200,000 – $250,000/year. Actual compensation will vary based on individual factors, including market location, relevant experience, and role scope. In addition to base salary, this role is eligible for variable compensation tied to performance or quota attainment, where applicable. WithCoverage’s Total Rewards package for full-time employees also includes equity participation and comprehensive benefits. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.

What We Offer:

• 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