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Salary: USD 170,000 - 210,000 / annual
WithCoverage is an AI-powered insurance brokerage platform that replaces traditional risk management with modern technology. Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), the company has raised $43M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. WithCoverage partners with over 1,000 high-growth companies including GoPuff, Eight Sleep, Bombas, and Blank Street Coffee, serving consumer brands, hospitality leaders, general contractors, advanced manufacturers, and defense contractors.
Reporting to the Head of Finance, you will build the accounting foundation for a rapidly scaling fintech company. Your first six months will focus on five critical areas:
1. Premium Trust Management: Own client money flows (eight figures monthly), reconcile payments to carriers weekly by customer and policy, clear payment backlogs, and establish carrier reconciliation as an automated control rather than a manual cleanup process.
2. Revenue Recognition: Build and own the complete revenue recognition system including policy schedules, expected vs. received revenue against carrier statements, cancellations, endorsements, return commissions, and flat fees. You will close every number and defend it.
3. Corporate Books & Compliance: Own monthly close, GAAP financials, and the compliance calendar including surplus lines taxes, 1099s, and state filings. While a bookkeeper processes transactions and external preparers file returns, you own the numbers and deadlines.
4. Automation: Identify and automate recurring processes including statement reconciliations, invoice deltas, remittance reading, unapplied cash tracking, and refund management. You will leverage AI and tooling to eliminate manual work.
5. Financial Systems Design: Restructure the chart of accounts, department mapping, and event attribution so the company understands where money is earned and spent without re-deriving it each close. Prepare for a 2027 audit with documented policies, source-dated evidence, clean payroll and equity records, and no plugs.
You will not manage direct reports initially; your leverage comes from what you build and automate. This is a high-impact individual contributor role with significant scope and autonomy.
REQUIREMENTS:
- CPA certification required
- Mix of Big 4 public accounting and high-growth industry experience
- Brokerage accounting knowledge (trust funds, agency vs. direct bill, commission structures, premium finance) or demonstrated ability to learn quickly
- Proven track record of automating recurring work; SQL proficiency preferred
- Experience as a number-two to a controller or similar finance leader
- Comfort with new tools and platforms (QuickBooks, modern billing systems, homegrown tooling)
- Systems-thinking approach to accounting; ability to design controls that run as automated tests
- Judgment-based reconciliation skills; ability to catch entries that balance but are incorrect
- Willingness to own work outside your immediate lane
