Finance Lead

Finance Lead

Location: New York, NY or Remote
Job Type: Full-Time

Salary will be commensurate with experience and expertise.

 

About WithCoverage:

WithCoverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—brands like GoPuff, Eight Sleep, Harry’s, Bombas, AG1, and Blank Street Coffee—so they can move fast without compromise.

Instead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.

Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), WithCoverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.

We’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.

 

Why Join Us:

• Grow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.
• 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 great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.

About The Role:

We’re hiring an experienced FP&A and finance lead to own planning, forecasting, and decision support end-to-end. You must be a senior but in-the-weeds operator. You’ll report to leadership as the point person for the financial model, monthly reporting and ad hoc requests. You will also take ownership of the billing, AR/AP and treasury functions of the business.

What You’ll Do:

•  Own our commissions and fee ledger: ensure accuracy, compliance with our 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 and billing system.
• Own the financial model (P&L, cash flow, balance sheet): maintain a dynamic driver-based model; run monthly forecasts; build scenarios and sensitivities.
• KPI analytics: define and track company and department metrics (revenue, margins, CAC/LTV, payback, cohort trends, pipeline, retention/churn, unit economics).
• Cash & runway: create 13-week cash forecasts; monitor actuals and track burn; highlight risks/opportunities and recommendations.
• Headcount & OPEX planning: provide leaders the financial data necessary to manage hiring plans, compensation bands, marketing budgets and vendor spend.
• Billing: Ensure payments are received and paid out correctly between clients and carriers. Work with the billing operations team to align actuals, accruals, and classification; reconcile model to books each month
• Treasury: Optimize yield on cash held in the business as well as funds held in trust on behalf of clients and carriers.
• Data & tooling: improve the finance data pipeline; standardize reporting and dashboards for self-serve visibility.

Who You Are:

• 5 to 8+ years in finance roles - insurance brokerage, startup/high-growth, or business-unit ownership.
• Track record of partnering directly with founders/CEOs in high-growth environments.
• Mastery of Excel/Google Sheets
• Experience building driver-based, three-statement models and cohort/retention analyses.
• Clear communicator with strong executive presence; comfortable working async with crisp written updates.
• NYC-based in office preferred. Secondarily, Chicago or Austin-based.
• Nice to Have:
• Experience with writing SQL to pull data for worksheets or dashboards
• Tools: Experience with Ramp, Rippling, and Ascend (an insurance billing platform)
• Prior experience with the insurance industry and/or SaaS/recurring-revenue metrics

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