About the job
Lead Risk Advisor
Location: New York, NY, Philadelphia, or Chicago
About WithCoverage:
WithCoverage revolutionizes the conventional insurance brokerage model through AI-enhanced risk management tailored for today's economy.
We collaborate with numerous high-growth, industry-leading companies such as GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clientele includes iconic consumer brands, hospitality pioneers, general contractors, advanced manufacturers, and next-generation defense contractors. They navigate intricate risk landscapes and seek a partner who can keep pace with their rapid evolution.
Rather than relying on a disjointed, manual brokerage system, we have established a new paradigm: elite risk advisors utilizing proprietary technology. Our proprietary Agency Management System provides our team and AI agents comprehensive visibility into policies, exposures, claims, billing, and commissions. This platform facilitates substantial automation, informed decision-making, and a significantly elevated service standard.
Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound), WithCoverage has secured over $43 million from premier investors including Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. We achieved more than 10x growth last year while remaining cash-flow positive, and we are just beginning to tap into our vast potential.
Our vision extends beyond merely enhancing brokerage services; we aim to transform how risk is managed throughout the economy.
Why Join Us:
- Accelerate Your Growth – Our rapid scaling offers you substantial opportunities to learn, lead, and influence your career and the future of the company.
- Impactful Work – We safeguard the world’s most innovative brands, including consumer icons, leaders in hospitality, and next-gen defense contractors.
- Redefine an Industry – The insurance sector is one of the largest and slowest-moving markets. We are rewriting the rulebook with proprietary technology, automation, and AI.
- Financial Incentives – We seek the best talent and invest in your future. This includes competitive compensation, meaningful equity, and exceptional benefits. We strongly believe in promoting from within and provide a clear pathway for everyone’s career advancement.
About The Role:
We are searching for a Lead Risk Advisor to manage client relationships from inception to completion while helping to scale a risk vertical. You will engage directly with business leaders...

