Product Designer

Product Designer

Location: New York, NY, or Philadelphia preferred

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.

About The Role:

As our first full-time Product Designer, you’ll shape the design vision for WithCoverage across both client-facing and internal platforms. You’ll collaborate closely with leadership and engineering to translate complex workflows into intuitive experiences, build our design system from the ground up, and influence the product direction at a fast-growing, Series A company redefining how businesses manage risk.

What You’ll Do:

• Lead all product design for WithCoverage, ensuring a consistent and unified design vision across our client-facing and internal platforms
• Collaborate seamlessly with product and engineering leadership, translating complex product requirements into intuitive, user-friendly designs
• Own the development and maintenance of a design system, including reusable components, patterns, and guidelines
• Actively contribute to product-level decision-making by participating in team meetings, cross-functional groups, and shadowing of day to day brokerage operations to identify workflow improvements

Who You Are:

• 2-5+ years of Design industry experience
• Experience designing enterprise-level B2B platforms and internal operating systems
• Familiarity with and focus on web-based design as opposed to mobile features
• Flexibility - we move quickly and believe the best features are the result of rapid iteration and incremental improvements
• Ambition and a desire to learn - to thrive on our team, you need to be curious, constantly learning, and comfortable navigating ambiguity to deliver innovative solutions
• (Preferred) Familiarity with basic frontend development concepts and a willingness to support our engineering team in these areas. For example, the ability to review and tweak simple UI/UX pull requests would be an advantage in this role.

For candidates based in the United States, the expected pay range for this position at the start of employment is $120,000 – $160,000/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