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:

As Claims Paralegal, you'll support claims across our book of commercial accounts, reporting to the Head of Claims, Phil Wilusz, and working closely with our Claims Counsel and Claims Managers. You'll keep every matter moving: preparing and submitting loss notices, gathering documentation from clients, tracking deadlines and carrier responses, and maintaining claim files that are complete and audit-ready.

Success depends on precision and follow-through, not just paperwork. In your first 90 days, success looks like getting fully up to speed on our active claims and Agency Management System; owning notice submissions and file maintenance for your assigned matters with no missed deadlines; and becoming the person the claims team relies on to know exactly where every claim stands.

What You'll Do:

• Support the full claims lifecycle across GL, Cyber, D&O, Property, and Marine/Cargo lines, including intake of new matters, preparing and submitting carrier notices, and tracking claims through to closure under the direction of Claims Counsel.
• Serve as a responsive point of contact for clients, gathering information and documentation, providing status updates, and helping keep carriers, counsel, and vendors coordinated and on schedule.
• Assist with coverage analysis by pulling and organizing policy forms, endorsements, and prior correspondence, and drafting initial versions of notice letters, demand letters, and routine carrier correspondence for attorney review.
• Support litigation and recovery efforts by tracking deadlines, managing document requests, organizing discovery and defense materials, and compiling loss documentation for property, cyber, and other first-party claims.
• Maintain high-quality, audit-ready claim files, ensuring all documentation, communications, reserves, and key dates are accurately recorded in our Agency Management System.
• Prepare claims reporting and data, including loss runs, claim summaries, and dashboard inputs that support renewal narratives and client program reviews.
• Help improve processes and tools, partnering with Claims Counsel, Operations, and Product to build templates, checklists, and automated workflows that make claims handling faster and more consistent.

What success looks like:

• Timely, accurate carrier notices and claim submissions with no missed deadlines.
• Complete, well-organized claim files that shorten cycle times and strengthen coverage positions and recoveries.
• High client satisfaction driven by responsiveness, clear communication, and predictable updates.

Who You Are:

• Experienced paralegal or claims professional with 2–5 years supporting commercial insurance claims, insurance litigation, or coverage matters within a carrier, law firm, or brokerage environment.
• Paralegal certificate and/or bachelor's degree preferred; familiarity with commercial policy forms (GL, Property, D&O, Cyber, Marine/Cargo) is a strong plus.
• Highly organized and detail-oriented, able to manage a high volume of active matters, deadlines, and documents without letting anything slip.
• Strong writer and communicator who can draft clear correspondence and interact professionally with clients, carriers, adjusters, and outside counsel.
• Tech-savvy and process-minded, comfortable working in claims or matter-management systems and eager to use automation and AI tools to work more efficiently.
• Collaborative and proactive, 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 OTE range for this position at the start of employment is $130,000 – $145,000 per 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, and major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture