WithCoverage

WithCoverage replaces traditional insurance brokers for fast-growing companies. Instead of relying on commission-driven brokers who profit when premiums rise, WithCoverage charges a flat fee and uses an AI audit engine to scan a client's existing policies, surface coverage gaps, benchmark pricing against carriers, and recommend a restructured risk strategy — on the first call. An in-house team of risk advisors, claims specialists, and insurance attorneys then executes placement end-to-end. Clients get a digital platform that manages policies, certificates of insurance, claims tracking, and billing in one place — replacing the usual tangle of emails and PDFs. Founded in 2023 by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound), the company targets high-growth businesses in consumer brands, hospitality, construction, advanced manufacturing, and defense contracting. Named clients include GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Over 700 companies have switched to WithCoverage in its first 18 months.

20 open roles

Website · Careers

Open roles

• Director, Property and Casualty — Brokerage + Risk | Myles · New York, NY or Philadelphia, PA; New York; Philadelphia
• VP, Property and Casualty — Brokerage + Risk | Myles · New York, NY or Philadelphia, PA; New York; Philadelphia
• Field Marketing Lead — Growth - Events & Marketing · New York, NY; New York
• Risk Team Director, Real Estate — Brokerage + Risk | Myles · New York City; New York
• Director, Channel Partnerships — Growth - Events & Marketing · New York, NY; New York
• Business Development Representative — Growth - Events & Marketing · New York, NY; Denver; Salt Lake City
• Director, Accounting — Finance | Cat · New York, NY; New York
• Member of Technical Staff, Automation Specialist — Product & Eng | Naveen · New York, NY; New York
• Executive Assistant — G&A | Max · New York, NY; New York
• VP, Growth — Growth - Events & Marketing · New York, NY; New York
• Marketing Ops Associate — Growth - Events & Marketing · New York, NY; New York
• Client Service Manager — Brokerage + Risk | Myles · Remote
• AVP, Property and Casualty — Brokerage + Risk | Myles · New York, NY or Philadelphia, PA; New York; Philadelphia
• Product Manager — Product & Eng | Naveen · New York, NY; New York
• Forward Deployed Engineer, Growth — Product & Eng | Naveen · New York, NY; New York
• Sr. Member of Technical Staff — Product & Eng | Naveen · New York, NY; New York
• AVP, Growth — Growth - Events & Marketing · New York, NY; New York
• Claims Paralegal — Claims | Phil · Remote
• Claims Manager — Claims | Phil · Remote
• Claims Support Specialist — Claims | Phil · Remote