Risk Advisor

Risk Advisor 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: We’re looking for a 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, partake in 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. • 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: • 2+ 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. • Strong critical thinking skills, with experience evaluating complex coverage programs, synthesizing risk, coverage, and cost considerations, and translating analysis into actionable strategies. • 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 $85,000 – $125,000/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