Lead Risk Advisor

Lead Risk Advisor

Location: New York, NY, Philadelphia, or Chicago
Job Type: Full-Time

Salary will be commensurate with experience and expertise.

About WithCoverage:

WithCoverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—brands like GoPuff, Eight Sleep, Harry’s, Bombas, AG1, and Blank Street Coffee—so they can move fast without compromise.

Instead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.

Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), WithCoverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.

We’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.

Why Join Us:

• Grow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.
• 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 great 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.

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