Product Designer

Location: New York, NY, or Philadelphia preferred
Job Type: Full-Time

With Coverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—100's of brands like GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee—so they can move fast without compromise.

Instead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.

Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), With Coverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.

We’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.

• Grow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.
• Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next‑gen defense contractors, and U.S. 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 great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.

As our first full‑time Product Designer, you’ll shape the design vision for With Coverage 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.

• Lead all product design for With Coverage, 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 day‑to‑day brokerage operations to identify workflow improvements.

• 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—quick iteration and incremental improvement are essential.
• Ambition and a desire to learn—curious, constantly learning, and comfortable navigating ambiguity to deliver innovative solutions.
• (Preferred) Familiarity with basic frontend development concepts and willingness to support engineering in these areas.

For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $110,000 – $140,000/year. Your exact offer may vary depending on multiple individualized factors, including market location, job‑related knowledge, skills, and experience. Total compensation may also include equity and employee benefits.

In addition to cash compensation, With Coverage offers a comprehensive Total Rewards package that includes equity grants.

• 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.
• 401(k) provider.
• Sick leave, family and medical leave, and flexible time off.
• Paid holidays (all major U.S. holidays).
• A curated in‑office employee experience, including catered lunches on Fridays for in‑office workers.
• A collaborative, transparent, and fun culture.