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 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