Executive Assistant

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.

• 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.

As our Executive Assistant, you will work directly with our co-founders. This is an opportunity to work alongside individuals who are driven by excellence and a passion for technology. The ideal candidate is a team player with exceptional communication skills, meticulous attention to detail and creative problem-solving skills. This role requires the ability to juggle competing responsibilities while prioritizing. Daily responsibilities include calendar management, coordinating meetings, travel and logistics, and prioritizing across multiple leaders. We are looking for someone with strong experience working with executive teams in fast-paced environments, and the ability to handle sensitive information with excellent judgment, diplomacy and discretion. This role will be based in our brand new Hudson Square office 5 days per week.

• Own and defend multiple executive calendars, including recurring meetings, resolving complex conflicts and exercising judgment about what gets time and what gets moved

• Coordinate high-stakes meetings end to end, board meetings, investor updates, client and carrier meetings, executive offsites, and leadership staff meetings — including attendee communications, venue coordination, A/V setup, catering, and preparation of program materials

• Proactively manage inbound communication and respond to urgent inquiries from internal and external stakeholders on the executives' behalf

• Prepare executives for what's next: assemble briefing materials, pull background on the people and companies in the room, and make sure they walk in ready

• Organize and compile data and content to support executive