Lead Risk Advisor New York, NY or Philadelphia, PA

With Coverage, Inc.; New York (NY); On-site; USD 140,000 - 190,000; Full time

Benefits offered by this job

Competitive equity and compensation

Comprehensive health benefits (medical

Pre‑tax accounts (FSA, HSAs)

Time Off and holidays

Curated in-office experience

Collaborative culture

Job summary

WithCoverage is seeking 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.

You will partner with Growth, Product, and Ops to ensure seamless execution and a differentiated client experience, translating needs into actionable insights for underwriting and operations.

Qualifications

• 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.
• 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.

Responsibilities

• 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.

Job description

Location: New York, NY, or Philadelphia, PA

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 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 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

Are you legally authorized to work in the United States? *

Will you now or in the future require sponsorship for an employment visa? *

As set forth in WithCoverage’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service‑connected disability.

A "recently separated veteran" means any veteran during the three‑year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.