Member of Technical Staff - Automation Specialist

Location: New York, NY

About

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy. We partner with hundreds of 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 $50M 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.

About the role

We are open to a wide range of levels for this role. As a member of our R&D organization, you’ll help build the systems that serve our clients’ complex risk needs. You’ll work directly inside real insurance servicing workflows, learn how they operate in practice, and then systematically automate them. For every workflow you own, you’ll execute the work, identify the decisions and edge cases involved, help design the automation, and operate the remaining exceptions as automation improves. Once a workflow becomes effectively zero-touch, you’ll move on to the next one. This role sits at the intersection of operations, analytics, and technology. You should be exceptionally comfortable with computers, structured problem solving, data, and technical tools. You might have used Python, SAS, MATLAB, SQL, or similar tools in prior work; built models or analyses; automated parts of your own workflow; or developed a reputation for being the person who figures out how systems work and makes them better.

Responsibilities

• Own workflows end to end. Take responsibility for real servicing workflows, from receiving a request through delivering the final result. Learn the process by doing the work yourself and develop a detailed understanding of the inputs, decisions, dependencies, and exceptions involved.
• Use technical tools to solve operational problems. Work with structured and unstructured data, spreadsheets, scripts, APIs, internal tools, and AI systems to investigate problems, improve workflows, and create leverage.