Backed by Sequoia.
About the 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.
What they're looking for
- You are an exceptionally strong analytical problem solver. You can take a messy, ambiguous process and break it into its underlying rules, decisions, and edge cases
- You are highly precise and detail-oriented. You can operate complex workflows accurately while simultaneously thinking about how to redesign them
- You communicate clearly with both technical and non-technical teams and can turn what you learn from operating a workflow into precise requirements for how it should be automated
- You are comfortable with a role that continually changes. As one part of your job becomes automated, you expect to take on the next unsolved problem
More about this role
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...
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