GTM Lead - Real Estate

About

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.

Responsibilities

• 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, capital partners and lenders, industry associations, and the brokerage community.
• Represent With Coverage at industry events like 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.
• 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.

Requirements

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).

Qualifications

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

Personally felt the pain of buying or managing real estate insurance (property, GL, builders risk, environmental, EPLI)

Skills

Commercial real estate or real estate-adjacent operating, advisory, or sales roles

Working knowledge of real estate operations

Relationship management and networking skills

B2B sales instincts

Excellent communication and executive presence

Ability to learn quickly about insurance products

Benefits

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

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