We are looking for a GTM Lead - Real Estate with 4+ years of experience to own and scale WithCoverage's expansion into the commercial real estate vertical. You should be deeply networked in the real estate industry — someone who already has relationships with commercial developers, property managers, and real estate C-suite leaders. This is a unique opportunity to build a go-to-market strategy from the ground up, leveraging an existing playbook that's already working across other verticals, while bringing your own industry expertise and connections. You'll be joining a team backed by Sequoia, 8VC, and Khosla Ventures that's disrupting the $1T+ insurance brokerage industry with AI-powered risk management. The role is heavily relationship-driven — think dinners, seminars, speaking engagements, and events rather than cold calls.

What will you be doing?

Leverage your existing network in commercial real estate to generate top-of-funnel pipeline through dinners, events, seminars, and speaking engagements
Build and execute the go-to-market strategy for the real estate vertical using proven frameworks from other successful verticals at WithCoverage
Develop deep relationships with real estate industry leaders, associations, and connectors to drive qualified opportunities
Own the full conversion cycle — from pipeline generation through deal execution — with quota responsibility
Collaborate with the Insurance Lead to shape the sales playbook and provide product feedback specific to real estate clients

WithCoverage is redefining risk management for the modern economy. Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound), WithCoverage replaces the traditional insurance brokerage with an AI-supercharged risk management solution designed for ambitious, high-growth businesses.

The insurance brokerage industry has long left businesses overpaying for coverage, inadequately protected, and stuck with a non-transparent, disorganized experience. WithCoverage changes that by combining an elite team of risk advisors, attorneys, and claims professionals with proprietary technology to deliver a holistic, continuous risk management service.

WithCoverage partners with hundreds of category-defining companies including GoPuff, Eight Sleep, Bombas, Chomps, Blank Street Coffee, Hungryroot, Salt & Straw, and Happy Dad. Clients span iconic consumer brands, hospitality leaders, general contractors, advanced manufacturers, and next-generation defense contractors operating in complex risk environments.

Backed by over $43M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners, WithCoverage's ambition is not to build a better brokerage — it's to redefine how risk is managed across the economy.

The company operates as a subject matter expert across multiple verticals including CPG, restaurants, hospitality, technology, construction, manufacturing, transportation, private equity, and real estate — with plans to expand into medical and data centers.

Unlike traditional brokers who operate as generalists and only show up at renewal time, WithCoverage provides a continuous service where clients pay a flat fee based on the complexity of their business and gain access to attorneys, claims professionals, risk advisors, and an AI-powered platform — all on a single engagement.

GTM Lead - Real Estate

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