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 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. This is a senior individual contributor role today, with a path to building and leading the Real Estate Risk function as the book grows. You'll set the technical bar, codify best practices, and architect the playbooks, tools, and training that scale a high-performing vertical practice.

What You’ll Do:

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

Who You Are:

10+ years of experience in commercial insurance or risk management, with deep specia…