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Risk Team Lead / Director

Location: New York, NY or Philadelphia, PA

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 Director of Risk Management, you'll lead our strategy and execution for client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. You'll partner closely with advisors, service teams, and executive leadership to deliver world-class risk solutions that drive retention, growth, and operational excellence.

What You'll Do:

• Directly responsible for client retention, client servicing, and oversight on new client placements across WithCoverage's Risk Advisory Team
• Manage a growing team of Risk Advisors to ensure all conversion, execution, and servicing timelines are met
• Monitor and address performance metrics with Risk Team to ensure performance expectations are met across a rapidly growing client base.
• Maintain a culture of excellence across the 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 across multiple industries and lines of business (P&C, Workers Comp, Auto, Cyber, etc.)
• Partner with Risk Advisors to deliver comprehensive renewal and risk mitigation strategies
• Partner with Risk Advisors to oversee loss analysis, benchmarking, and claims trends to guide client decision-making and carrier negotiations
• Partner with Risk Advisors to evaluate client operations, exposures, and contractual risks to propose proactive solutions
• Support internal education and development of best practices across the risk team
• Collaborate with leadership to enhance processes, tools, and technology for risk advisory delivery

Who You Are:

• 8-12 years of experience in commercial insurance or risk management, 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 understanding of commercial lines (GL, Property, Auto, WC, Umbrella, and Specialty)
• Proven ability to communicate complex insurance concepts to executive-level clients in a clear, advisory tone
• Strong analytical and strategic thinker, comfortable working across clients and industries
• Leadership mindset with a desire to mentor others and build scalable systems for growth
• Designations (CPCU, ARM, CIC, CRM) 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 - $300,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. This role may also be eligible for additional variable compensation, including quota-based incentives where applicable. WithCoverage offers a comprehensive Total Rewards package for full-time employees, which includes equity grants and a robust suite of benefits.

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, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture