About WithCoverage:

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy. We partner with over one thousand 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:

Your first 6 months: Reporting into the Head of Finance, we’re going from 0 → 1 and Accounting is the foundational pillar that gets us there.

• Own the premium trust. Client money, eight figures a month, tied to the bank weekly down to the customer and policy. Clear the backlog of payments carriers never applied, then make carrier reconciliation a control that runs, not a cleanup that repeats.
• Build our rev rec. Policy, schedules, expected vs received against carrier statements, cancellations, endorsements, return commission, flat fees. You build it, you close it, you defend every number.
• Own the corporate books. Monthly close, GAAP financials, and the compliance calendar: surplus lines taxes, 1099s, state filings. Our bookkeeper processes and external preparers file; you own the numbers and the deadlines.
• Automate everything that repeats. Statement recs, invoice deltas, remittance reading, unapplied cash, refund clocks. If it shows up twice, build it or point AI at it.
• Make the numbers decide things. Take a view and rechart the accounts, department mapping, and event attribution so we know where money is earned and spent without re-deriving it every time.
• Get us audit ready for 2027. Documented policy, evidence dated at the source, payroll and equity comp, clean opening balances. No plugs.

Who You Are:

• CPA with a mix of Big 4 public accounting and high-growth industry roles.
• You know brokerage accounting, or you'll learn it fast. Trust funds, agency vs direct bill, commission and return commission, premium finance.
• You automate before you ask for headcount. You've killed a piece of recurring work for good and can walk us through how. SQL doesn't scare you.
• You think of the books as a system, not a stack of workbooks. Our subledgers are v1: built in code, controls that run as tests. Tomorrow's version is yours to shape.
• Agents do the reconciliation. You own what the entries mean. Only a person catches an entry that balances but is wrong. Every close is gated on your judgment.
• You've been the number two to a great controller and you want the wheel. No direct reports to start. Your leverage is what you build, not who you manage.
• Scope excites you. Billing questions, carrier weirdness, a control nobody's built before. You grab the thing outside your lane.
• New tools don't intimidate you. QuickBooks, a modern billing platform, homegrown tooling where nothing off the shelf fit yet. Part of your job is deciding what this stack becomes.

For candidates based in the United States:

The expected pay range for this position at the start of employment is $170,000 – $210,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. This role may also be eligible for additional variable compensation, including quota-based incentives where applicable. WithCoverage offers a comprehensive Total Rewards package for full-time employees, which includes equity grants and a robust suite of benefits.

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