Director, Enterprise Growth
About The Position
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.
Requirements
- 5-10 years of experience with hands-on ownership of clients or deal relationships.
- Strong external presence with the judgement to represent our CEO and the company externally.
- Sound judgment in high-stakes interactions with clients and partners.
- Comfortable operating with significant ambiguity and shifting priorities.
- A track record of driving deals forward independently end to end.
- Highly organized with exceptional attention to detail and a bias toward action.
- High ownership mindset: proactive, resourceful, and able to work with minimal direction.
- An enterprise AE or sales manager profile with unusually strong structure and follow-through.
- A similar "extension of the executive" role at a growth-stage company.
- A senior consultant or deal-team professional with real relationship ownership experience, not just analysis or support.
Responsibilities
- Act as a direct force multiplier to our CEO while taking on an increasing share of our most important deal and client relationships.
- Drive our CEO's active pipeline forward.
- Represent the company in high-stakes client and partner conversations.
- Take full ownership of deals as your scope grows.
- Own our CEO's active pipeline end to end, including all follow-ups and next steps.
- Join top-of-funnel and key discovery calls, and own next steps.
- Drive urgency and coordinate the broader team on any deal where the CEO is personally involved.
- Take on an increasing amount of deal ownership over time, with the explicit goal of our CEO eventually being the growth owner on zero deals.
- Manage the client and partner relationships our CEO interacts with on a daily basis.
- Spend roughly two-thirds of time on closing the biggest deals and one-third on key growth initiatives.
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)
- 401(k) provider
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
