Head of Finance
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. 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.
Requirements
- 8+ years in finance roles in high-growth environments - insurance brokerage, startup/high-growth, or business-unit ownership.
- Track record of partnering directly with founders/CEOs in high-growth environments.
- Strong grasp of accrual-based revenue recognition
- Experienced preparing board-level financial materials and owning metrics accuracy
- Clear communicator with strong executive presence; comfortable working async with crisp written updates.
- NYC-based in office
Nice To Haves
- Prior experience with the insurance industry
Responsibilities
- Financial Strategy. Own the 3-statement model. Maintain a dynamic driver-based growth model. Run monthly forecasts. Build out scenarios and sensitivities. Model and diligence potential M&A transactions.
- Accounting: Initially oversee Controller responsibilities directly, hiring a team within the first 6-12 months. Oversee the GL & close process with our outsourced accounting team. Ensure accuracy & compliance with carrier and client terms, and provide insight into account profitability. Ensure every transaction is accurately tied to the correct policy, insurance carrier, and client account in our agency management system.
- Board & Investor Reporting: KPI analytics: define and track company and department metrics (revenue, margins, CAC/LTV, payback, cohort trends, pipeline, retention/churn, unit economics).
- Headcount & OPEX planning: provide the data necessary to manage hiring plans, compensation bands, quota strategy, marketing budgets and vendor spend.
- AP/AR: Ensure payments are received and paid out correctly. Work with the billing operations team to reconcile our model to books in real-time.
- Data & tooling: improve the finance data pipeline; standardize reporting and dashboards for self-serve visibility.
Benefits
- 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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What This Job Offers
Job Type
Full-time
Career Level
Executive
Education Level
No Education Listed
