Claims Counsel

Location: Preference for New York, NY, Philadelphia, Chicago, or Austin, but open to Remote

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. We grew more than 10x last year while cash-flow positive, and we are very early in the opportunity.

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.

What You’ll Do:

• Own complex claims end-to-end across GL, Cyber, D&O, Property, and Marine/Cargo lines—triaging new matters, confirming coverage, coordinating carrier notices, and driving resolution strategies through to closure.
• Serve as the primary client advocate, translating coverage and litigation issues into clear guidance, managing expectations, and aligning carriers, counsel, and vendors around the client’s best outcome.
• Analyze and negotiate coverage positions, drafting demand and rebuttal letters, challenging denials, and securing optimal defense and indemnity contributions from insurers.
• Oversee litigation and recovery efforts, ensuring defense and coverage counsel strategies align with policy recovery, and leading loss quantification for property, cyber, and other first-party claims.
• Manage external partners and internal team members, setting standards for claims handling, mentoring analysts, and maintaining high-quality, audit-ready files and documentation.
• Deliver insights and reporting through claims data, dashboards, and renewal narratives—identifying trends, coverage gaps, and opportunities to improve client programs and outcomes.
• Continuously improve processes and tools, partnering with Operations and Product to streamline claims workflows, automate documentation, and enhance the client experience.

What success looks like:

• Shortened claim cycle times and increased recovery/indemnity percentages (especially in the first‑party).
• Fewer coverage disputes/denials through early positioning and escalations that stick.
• High client satisfaction (clear communication, predictable updates, strong outcomes).

Who You Are:

• Experienced claims professional with 5–10 years managing complex commercial insurance claims—ideally across GL, Cyber, D&O, Property, and Marine/Cargo—within a carrier, law firm, or brokerage environment.
• Coverage-driven mindset with a J.D. and active bar membership; skilled in analyzing policy wording, drafting coverage positions, and advocating for insureds in high-stakes matters.
  Full-lifecycle operator comfortable owning claims from first notice through resolution, including coverage analysis, litigation oversight, negotiation, and first-party recovery.
• Client-focused communicator who can translate complex coverage and litigation issues into clear business guidance, maintaining calm and credibility with executives during live incidents and negotiations.
• Hands-on leader and mentor able to review and elevate team output, establish standards, and help build playbooks, templates, and scalable claims processes.
• Analytical and process-minded, leveraging data, metrics, and technology to manage performance, improve consistency, and drive efficiency.
• Collaborative and entrepreneurial, thriving in a fast-moving startup setting with strong judgment, humility, and a bias toward action and continuous improvement.

For candidates based in the United States, the expected pay range for this position at the start of employment is $150,000 – $190,000/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 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