GTM Lead – Real Estate

GTM Lead - Real Estate

Location: New York, NY

About WithCoverage:

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.

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:

Join With Coverage as a GTM Lead - Real Estate on the Growth team - you’ll own and scale one of our fastest-growing verticals end-to-end. This is a sales-driven leadership role where you’ll drive growth of the Real Estate vertical across the full conversion cycle, build deep industry relationships, and lead all aspects of deal execution.

We’re looking for someone who wants ownership, thrives in high-performance environments, and is eager to accelerate their career by building something meaningful. You’re motivated by results, comfortable operating with autonomy, and willing to put in the work required to achieve outsized outcomes as you directly shape the growth of one of our key business verticals.

What You’ll Do:

• Own the vertical’s growth. Become the true owner of a key business line as the Vertical Lead responsible for pipeline generation, relationship development, and deal execution.
• Drive execution. Generate demand through targeted outreach, manage the pipeline, and guide prospects through the full conversion cycle with clear communication and follow-through.
• Develop industry relationships. Develop a deep understanding of your vertical and build deep relationships with industry C-suite leaders, associations, and connectors.
• Shape the GTM playbook. Shape the sales playbook in partnership with an Insurance Lead and give product feedback to address the needs of your customers
• Build pipeline. Expand referral networks and identify new go-to-market opportunities to consistently grow qualified opportunities.

Who You Are:

• 4+ years in relevant fields (high-growth startups, management consulting, or investment banking/PE/VC)
• Expert relationship manager and networker, with capacity to excel in B2B sales closing 6-7 figure deals
• Excellent communication and executive presence – you will represent the brand
• Quick learner

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $200,000 – $250,000/year. Actual compensation will vary based on individual factors, including market location, relevant experience, and role scope. In addition to base salary, this role is eligible for variable compensation tied to performance or quota attainment, where applicable. WithCoverage’s Total Rewards package for full-time employees also includes equity participation and comprehensive benefits.

What We Offer:

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
• Human Interest: 401(k) provider
• Time Off: Flexible time off, sick leave, family and medical leave, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture