Director, Enterprise Growth

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:

As our Director, Enterprise Growth, you will act as a direct force multiplier to our CEO while taking on an increasing share of our most important deal and client relationships. This is a hybrid strategic + customer-facing role designed for someone who thrives in fast-moving environments, has real judgment under pressure, and is excited to build a company from the ground up. You'll play a pivotal part in driving our CEOs active pipeline forward, representing the company in high-stakes client and partner conversations, and taking full ownership of deals as your scope grows. If you want a seat at the table in high-visibility, high-stakes moments and are ready to grow into owning the relationships that matter most, this role is uniquely positioned for that.

What You'll Do

• You'll be focused on driving WithCoverage's growth engine forward as quickly and efficiently as possible. You'll directly own enterprise deals and VIP relationships.




• Own our CEOs 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.


• Your time would be roughly split between two thirds on closing the biggest deals and one third on key growth initiatives.

Who You Are

• 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.

You likely come from one of these backgrounds:

• An enterprise AE or sales manager profile with unusually strong structure and follow-through.


• Someone who has held 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.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $180,000 – $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