Claims Counsel

Remote Remote February 25, 2026

Claims Counsel

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

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