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GTM Lead

New York, NY

GTM Lead

Location: New York, NY

About WithCoverage:

WithCoverage replaces the traditional insurance brokerage with an AI-supercharged risk management team 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 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:

We are hiring GTM Leads to build and own some of the most important verticals in our business. This is not a traditional sales role. It is a true GM seat with full ownership of a vertical’s growth, revenue, relationships, and market presence.

You will be responsible for making WithCoverage the dominant risk partner in your category. That means closing six and seven figure accounts, building strategic partnerships, developing industry relationships, creating demand, and establishing our reputation with the people and companies that matter most.

We are looking for builders and operators who have done this before. Built a pipeline from a cold start, owned the full cycle, and earned trust at the C-suite level. If you are at your best when you have real ownership, the pricing and product to win, and a short distance between you and the decision, this is the seat.

The best GTM Leads are equally comfortable closing a major account, hosting a dinner with industry leaders, building relationships with investors and operators, speaking at an event, or developing the playbook that scales a category.

What You’ll Do:

  • A vertical, end to end. Own one of our priority categories like a business. You are responsible for revenue growth, market presence, strategic relationships, pipeline generation, and the long-term reputation of WithCoverage within the category.
  • The full deal cycle. Build target lists, drive outbound, qualify, run discovery, structure the program with our underwriting team, and close. You stay in the seat from first touch to binding.
  • The relationship map. Develop senior relationships across founders, CEOs, CFOs, GCs, industry associations, capital partners, and the connectors who shape deal flow in your vertical. Be the person the category calls. Build and maintain relationships through conferences, events, dinners, operator communities, referral networks, and strategic partnerships. Create opportunities before they formally enter the pipeline.
  • The GTM playbook. Partner with the Insurance Lead for your vertical to refine ICP, messaging, packaging, and the underwriting story. Bring structured product and pricing feedback that compounds into a better offering. Shape how WithCoverage wins in the category. Influence positioning, partnerships, market strategy, and customer experience based on what you learn in the field.
  • The team you scale. As you prove out the playbook, hire and develop the team underneath you. The right person grows into the GM or Head of Vertical seat.

Who You Are:

  • 5+ years in business development, growth, consulting, investing, partnerships, sales or other relationship driven roles, with a track record of creating opportunities and driving commercial outcomes
  • You have built a pipeline from a cold start before. Outbound, referral, and category-driven motions are all in your toolkit
  • Credible at the C-suite and principal level. You have sat across the table from founders, CFOs, GPs, and operators and earned the room
  • Strong instincts for how to package a complex, consultative sale. You can explain why a customer should switch, what to buy, and what good looks like, without leaning on a deck
  • High-ownership operator. Comfortable with ambiguity, fast-moving, and willing to put in the work to compound a vertical from the ground up
  • Excellent written and verbal communication and executive presence. You are the face of the brand in your category
  • You are a relationship builder. You enjoy creating opportunities through networks, partnerships, events, referrals, and community building, not just traditional outbound
  • You think like an owner and are excited by the idea of building a category, not simply managing a quota

Nice to Have

  • Background in consulting, venture capital, private equity, growth equity, strategic partnerships or other commercially-oriented roles where relationship building and business development were critical to success
  • Vertical depth in any of our priority categories (CPG, real estate, financial services (private equity, growth equity, venture capital), technology, manufacturing, professional services, healthcare) is a plus.

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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