Chief of Staff + GTM Lead

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. We grew more than 10x last year while cash-flow positive, and we are very early in the opportunity.

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 Chief of Staff & Sales Lead, you will act as a direct force multiplier to the CEO while helping drive the company's early revenue engine. This is a hybrid strategic + customer-facing role designed for someone who thrives in fast-moving environments, loves solving ambiguous problems, and is excited to help build a company from the ground up. You'll play a pivotal part in aligning the organization, accelerating decision-making, supporting sales conversations, and ensuring early customers have a seamless, high-value experience. If you want a seat at the table and enjoy wearing multiple hats, from operations to GTM to customer success, this role is uniquely high-impact and high-visibility.

What You'll Do:

• To make things simple – You'll be 100% focused on growing WithCoverage as quickly and efficiently as possible. You'll directly own the most important initiatives to get this done.
  • Act as an extension of the CEO to drive alignment, follow-through, and execution across the company.
  • Lead project management for cross-functional initiatives (launches, implementations, partnerships) to keep the company operating smoothly.
  • Support and eventually lead sales activities—including joining discovery calls, managing the pipeline, handling follow-ups, and driving deals toward close.
  • Manage CEO priorities, prepare materials for key meetings, and ensure decisions translate into actionable plans.

Who You Are:

• 2–6 years of experience across operations, chief of staff, sales, consulting, or other generalist roles.
• A strong communicator who can represent the CEO internally and externally with clarity and polish.
• Comfortable in sales calls - can ask thoughtful questions, handle objections, and drive next steps.
• A builder of processes and systems, especially in zero-to-one environments.
• Highly organized with exceptional follow-through and attention to detail.
• Thrives in ambiguity and enjoys switching between strategic planning and hands-on execution.
• High ownership mindset - proactive, resourceful, and able to work with minimal direction.
• Comfortable with data, dashboards, CRM tools, and basic GTM metrics.
• Trustworthy and discreet, with the judgment to handle sensitive information and represent leadership effectively.

For candidates based in the United States, the expected OTE pay range for this position at the start of employment is $150,000 – $200,000/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 may include equity
• Flexible paid time off
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA 
• Commuter Savings Account
• Human Interest: 401(k) provider
• Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
• Paid Holidays: Observance of all major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
• Collaborative, transparent, and fun culture

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