About WithCoverage :
WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy.
We partner with over one thousand 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
We're looking for an exceptional operator to join our Founders' Office and work directly with our co-founders on some of WithCoverage's most ambitious commercial initiatives.
As we scale, we're pursuing opportunities that don't fit neatly within an existing team. These might include launching a new business line, validating a strategic partnership, entering a new market, or bringing an entirely new commercial model to life. Many of these opportunities have the potential to generate millions of dollars in revenue and materially change the trajectory of the company.
You'll take these ideas from concept to execution. That means assessing the opportunity, developing a strategy, building the right relationships, and doing whatever it takes to get something off the ground.
This is not a traditional strategy or Chief of Staff role. You won't research opportunities, prepare recommendations, or coordinate execution. You'll own initiatives from start to finish and be accountable for delivering results.
The ideal candidate combines exceptional problem-solving ability with strong commercial instincts, creativity, and relentless follow-through. You can operate comfortably with senior executives, but you're equally willing to get into the details and do the work yourself.
What You'll Do
Own high-impact special projects end to end. Take ambitious ideas from the founders, evaluate their potential, develop a plan, and independently drive execution through launch.
Build new commercial opportunities. Identify and pursue new markets, business models, strategic partnerships, and distribution channels with meaningful revenue potential.
Launch zero-to-one initiatives. Validate demand, develop business models, secure initial customers or partners, and build the infrastructure necessary to bring new opportunities to market.
Build strategic external relationships. Represent WithCoverage with founders, executives, investors, and prospective partners. Develop relationships that create meaningful commercial opportunities.
Drive cross-functional execution. Work across…