Risk Team Director - Real Estate

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 solutionsBuild 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 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
• 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