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GTM Lead - Real Estate

New York, NY

GTM Lead - Real Estate

Location: New York, NY or Remote

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 our Real Estate Growth Lead. You will own and scale one of our fastest-growing verticals end to end. Commercial real estate owners, operators, developers, and managers face a uniquely complex risk profile: property, general liability, builders risk, environmental, EPLI for property managers, D&O, umbrella, and rising exposures from cyber and climate. Your job is to become the go-to broker for these operators and build the relationships, pipeline, and playbook that make us the default choice in the category.

This is a sales-driven leadership role. You will drive the full conversion cycle, develop deep industry relationships, and lead deal execution. We are looking for someone who wants real ownership of a vertical, thrives in a high-performance environment, and is energized by building something meaningful in a category they understand at a gut level.

What You’ll Do:

  • Own the Real Estate vertical. Be the true owner of one of our most strategic business lines, accountable for pipeline, relationships, and revenue.
  • Drive the full conversion cycle. Generate demand through targeted outreach, run a clean and prioritized pipeline, and guide prospects through quoting, binding, and onboarding with clear communication and follow-through.
  • Build the Real Estate relationship map. Develop deep relationships with principals, GPs, asset managers, and CFOs at owners, developers, syndicators, REITs, and property managers, plus the broader ecosystem: real estate and prop tech investors (e.g., Fifth Wall, MetaProp, Camber Creek, Moderne Ventures, Navitas Capital), capital partners and lenders, industry associations (BOMA, NAIOP, IREM, ICSC, ULI, NAA, NMHC), and the brokerage community.
  • Be present where the category is. Represent With Coverage at ICSC Las Vegas, ULI Fall and Spring Meetings, NAREE, NMHC Annual Meeting, NAA Apartmentalize, and other industry events; cultivate the connectors who shape deal flow.
  • Shape the GTM playbook. Partner with the Real Estate Insurance Lead to refine messaging, packaging, and ICP definition; bring structured product and underwriting feedback that reflects how real estate operators actually buy and what they need.
  • Build a durable pipeline. Expand referral networks (capital partners, mortgage brokers, prop tech founders, real estate attorneys, accountants) and identify new go-to-market motions to consistently grow qualified opportunities.

Who You Are:

  • 4+ years in commercial real estate or real estate-adjacent operating, advisory, or sales roles. Examples include an owner, operator, developer, REIT, syndicator, or property manager (acquisitions, asset management, finance, IR, BD), a real estate or prop tech VC, a CRE brokerage, a real estate lender or capital markets desk, or management consulting / investment banking with significant real estate coverage
  • Working knowledge of how real estate operators actually run: asset classes (multifamily, office, retail, industrial, mixed-use), deal structures (GP/LP, JVs, syndications, fund vehicles), property management economics, and the risks that come with each stage from development to disposition
  • Proven relationship manager and networker. You have built and worked a category network, and you can credibly sit across the table from a principal, asset manager, CFO, or capital partner
  • Strong B2B sales instincts; comfort owning six to seven figure deals from prospect to close
  • Excellent written and verbal communication and executive presence. You will be the face of the brand in this category
  • High-ownership operator: comfortable with ambiguity, fast-moving, and willing to put in the work to compound a vertical from the ground up
  • Quick learner who can get smart on insurance products fast (we will teach you)

Nice to Have:

  • Existing relationships across CRE owners and operators, prop tech investors, capital partners, or industry associations (BOMA, NAIOP, IREM, ICSC, ULI, NAA, NMHC)
  • Prior experience in insurance, financial services, or another regulated B2B sale
  • Have personally felt the pain of buying or managing real estate insurance (property, GL, builders risk, environmental, EPLI) and have opinions about what is broken

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. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.

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, and major national holidays
  • A curated in-office employee experience, designed to foster community, team connections, and innovation
  • Collaborative, transparent, and fun culture

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