GM, Outbound

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.

WithCoverage has 1,000+ customers and has built that almost entirely on word of mouth, warm introductions, and events. That engine works — but it only reaches as far as our network does. The next order of magnitude comes from accounts that have never heard of us.

This role owns Outbound at WithCoverage, end to end: the strategy, the system, and the number. But the mandate is bigger than running channels well. We want to build an AI-first outbound engine — one always-on system that warms our entire TAM, reads intent signals off that engagement, and routes every account into the right conversion motion automatically. Cold email, cold calling, cold social, gifting, and our named-account ABM program stop being five separate programs and become surfaces that one engine acts through.

We're looking for the operator who builds it. Today outbound is several motions at different stages of maturity: a BDR team that produces our largest share of top-of-funnel but hasn't yet cracked cold conversion economics, a young cold email program, and an early ABM push against our top-tier targets. All of it is run by humans, campaign by campaign. Your job is to make them one system, get the funnel math to work, and then let the system scale in a way headcount can't. When this converts profitably, we will invest behind it aggressively.

This is a senior, hands-on role. You own the strategy, the system, and the outcome — and you carry the number.

• Build the engine, not just the campaigns. Own the architecture above and the roadmap to get there from where we are today. You'll partner closely with Growth Product & Engineering on tooling, signal infrastructure, and data — and you'll be specific about what you need