Member of Technical Staff

WithCoverage replaces the traditional insurance brokerage with AI-driven 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 in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions.

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.

About The Role (open to a wide range of levels):

As a member of our R&D organization, you'll build AI-native products that help us serve our clients' complex risk needs. You'll work at the intersection of large language models, complex business workflows, and real production systems. You'll turn manual, expertise-heavy processes into reliable, autonomous capabilities. You'll ship agents that parse dense policy documents, automate email workflows, build knowledge representations of client risk profiles, and handle real client work end to end. You'll architect the systems that make these agents trustworthy, observable, and extensible so they can be deployed across workflows by the rest of the team. You'll craft APIs used by both the UIs you design and the AI agents you build. You'll solve hard AI problems, including task decomposition, tool use, memory, error recovery, human-in-the-loop patterns, and evaluation frameworks.

What You'll Do:

• Build AI-powered workflows: design and ship automations that solve real problems using LLMs, our internal agent platform, and whatever tools get the job done. Own the full lifecycle, from prototype to production deployment to ongoing improvement.
• Build for extensibility: create the abstractions, APIs, and patterns that let risk advisors ship workflow solutions quickly.
• Ship fast, iterate faster.
• Engineer reliable AI systems: architect agentic systems that work at scale, including multi-step reasoning, structured extraction from unstructured data, and multi-agent coordination. Build evaluation frameworks to measure agent quality, catch regressions, and iterate with confidence.

Who You Are:

• 4+ years of experience building software in production environments, with hands-on experience applying LLMs to real-world problems.
• 2+ years at the same company in a prior role, with demonstrated promotions and recognition.
• You've built AI-powered solutions that real users depend on. You understand prompt engineering and the challenges of making AI reliable in production.
• Strong software engineering fundamentals.

This role is on-site in our New York (Flatiron) office, 5 days/week. The expected cash compensation range for this position at the start of employment is $180,000 - $275,000/year, plus equity and benefits (comprehensive health coverage, 401(k) matching, flexible time off).