Chief of Staff

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.

About the Role

As our Chief of Staff, 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

• 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.

Pay

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