Director, Accounting

With Coverage 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.

With Coverage 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. With Coverage 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.

• 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.

Reporting to the Head of Finance, the Senior Accounting Manager owns the accounting function at With Coverage 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

• 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

• 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