Sr. Member of Technical Staff

Location: New York, NY

Job Type: Full-Time

About WithCoverage

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 $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.

Why join us

• 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.

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 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. Design systems that others can build on top of. Create the abstractions, APIs, and patterns that let risk advisors ship workflow solutions quickly without reinventing the plumbing. Your infrastructure should multiply the team’s output.
• Ship fast, iterate faster. You’re not building a roadmap six months out. You’re identifying problems this week and shipping solutions next week. Move quickly, measure impact, and iterate based on what is actually working for the team.
• 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: you write clean code, design sensible systems, and ship consistently.
• High EQ and strong communication skills. You can work closely with non-technical teams, understand their workflows deeply, and translate that understanding into practical solutions.

This role is on-site in our New York office. The expected cash compensation range for this position at the start of employment is $180,000 – $275,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. WithCoverage offers a comprehensive total rewards package for full-time employees, which includes equity grants and a robust suite of benefits.

What We Offer

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
• Human Interest: 401(k) provider
• Time Off: Flexible time off, sick leave, family and medical leave, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture