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