Director, Accounting

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:

Reporting to the Head of Finance, the Senior Accounting Manager owns the accounting function at WithCoverage and builds the insurance accounting system underneath it. We're going from 0 → 1. Accounting is the foundational pillar that gets us there.

Most Senior Accounting Manager roles are about running a close that already exists. This one is about designing it. We move client premium through a fiduciary trust account, and the policy-level subledger, carrier reconciliation, and commission revenue recognition that sit on top of it are yours. You'll have a dedicated bookkeeper handling transaction processing, AP, and AR, so your time goes to architecture, controls, and judgment, not data entry. You'll also have an external controller as a technical sounding board and a Head of Finance who will get you whatever you need.

This is a hands-on individual contributor seat that grows into that title and team as we scale

Your first 6 months:

Fiduciary and Premium Trust Accounting

• Own the premium trust: client funds reconciled to the bank and tracked to the customer and policy level
• Design and operate carrier reconciliation as a recurring control, including clearing the current backlog of unapplied carrier payments
• Establish the fiduciary liability accounting for premiums payable to carriers and return premiums payable to insureds

Revenue Recognition

• Build our commission revenue recognition under ASC 606, including policy-level schedules, expected versus received against carrier statements, cancellations, endorsements, return commission, and flat fees
• Own the revenue close and the defense of every number in it

Month-End Close and Financial Reporting

• Own the monthly close and GAAP financial statements, including the transition of corporate books from cash to accrual basis
• Review journal entries, balance sheet reconciliations, and accruals prepared by the bookkeeper
• Own the compliance calendar: surplus lines taxes, 1099s, and state filings, with external preparers filing

Systems and Automation

• Design the policy-level subledger and how it feeds the general ledger. QuickBooks stays as the GL and we build around it, using modern tooling and AI where it beats a spreadsheet
• Automate recurring work: statement reconciliations, remittance matching, unapplied cash, refund tracking
• Decide what the finance stack becomes as we scale

Controls, Policy, and Audit Readiness

• Rechart the accounts, department mapping, and cost attribution so the numbers can support decisions without being re-derived each month
• Document accounting policies and build the evidence trail to get us audit ready for 2027
• Partner with RevOps, Growth, and Operations on billing, commission, and carrier questions

Who You Are:

• CPA, with 7+ years of progressive accounting experience that includes Big 4 public accounting and an in-house role at a high-growth company
• You've worked a month-end close and have opinions on how it should be done better
• Strong command of US GAAP, with real experience applying ASC 606 to a business with variable and multi-stream revenue
• Experience with QuickBooks, NetSuite, or a similar GL, and comfort building around a system rather than waiting for a perfect one
• You automate before you ask for headcount. You've eliminated a piece of recurring work for good and can walk us through how, whatever the tool
• You think of the books as a system, not a stack of excel workbooks. Our subledger is yours to shape
• Comfortable operating in ambiguity and scope. Billing questions, carrier weirdness, a control nobody's built before. You grab the thing outside your lane
• Clear communicator who can explain technical accounting to non-accountants and push back when you disagree. The Head of Finance is not an accountant, and this role is the technical authority on the numbers
• Plus: You know brokerage accounting (trust funds, agency vs direct bill, commission and return commission, premium finance), or you'll learn it fast. Most strong candidates won't have this. Tell us how you'd get up to speed

For candidates based in the United States, the expected pay range for this position at the start of employment is $180,000 – $240,000/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