Lead Risk Advisor

Lead Risk Advisor

Location: New York, NY, Philadelphia, or Chicago

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. We grew more than 10x last year while cash-flow positive, and we are very early in the opportunity.

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:

We’re looking for a Lead Risk Advisor to own client relationships end-to-end and help scale a risk vertical. You’ll work directly with business leaders to assess exposures, lead Risk Analyses, and deliver tailored solutions that drive measurable impact.

What You’ll Do:

• Own and manage a portfolio of client accounts end-to-end, driving strong relationships and delivering exceptional service.
• Lead client-facing Risk Analyses with senior executives, diagnosing coverage gaps and presenting tailored insurance solutions.
• Build and refine playbooks for your vertical to create repeatable, scalable best practices for future advisors.
• Collaborate closely with the Growth, Product, and Ops teams to ensure seamless execution and a differentiated client experience.
• Translate client needs into actionable insights for underwriting, operations, and product improvements.
• Track and report key client metrics to identify opportunities for expansion, efficiency, and impact.
• Contribute to the culture of excellence, curiosity, and accountability that defines our team.

Who You Are:

• 4–7 years into your career, ideally with experience in commercial insurance, risk management, or client advisory roles.
• Confident leading high-stakes client conversations and comfortable presenting analyses or proposals.
• Deeply curious about how businesses operate and motivated to become a trusted advisor to their leaders.
• Strong communicator who thrives in fast-moving, collaborative environments.
• Highly detail-oriented and accountable — you own outcomes, not just tasks.
• Coachable and eager to learn; open to feedback and committed to growth.
• Drawn to environments where performance is rewarded with real upside and autonomy.
• Hardworking, kind, and humble — the type of teammate others want to work with.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $140,000 – $190,000/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.

What We Offer:

• Competitive compensation that may include equity
• Flexible paid time off
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA 
• Commuter Savings Account
• Human Interest: 401(k) provider
• Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
• Paid Holidays: Observance of all major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
• Collaborative, transparent, and fun culture