AI Agent Engineer

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. We grew more than 10x last year while cash-flow positive, and we are very early in the opportunity.

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're looking for an AI Agent Engineer to design, build, and scale the agent platform that powers our AI capabilities. You'll work at the intersection of large language models, complex business workflows, and real production systems—building the core infrastructure that turns manual, expertise-heavy processes into reliable, autonomous capabilities.

This is a high-ownership role. You'll ship the 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.

This isn't a role where you're configuring tools or wiring up APIs. You'll solve hard infrastructure problems: task decomposition, tool use, memory, error recovery, human-in-the-loop patterns, and evaluation frameworks. You'll build the foundation that our Applied AI Engineers deploy on top of.

What You'll Do:

• Build the Agent Platform. Design and implement the core agent infrastructure that powers automation across the business. Own the architecture—task orchestration, tool use, memory systems, and error handling patterns. Build systems that are reliable enough to handle real client work.
• Engineer Reliable AI Systems. Architect agentic systems that work at scale: 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.
• Build for Extensibility. Design the platform so others can build on top of it. Create the abstractions, APIs, and patterns that let Applied AI Engineers ship workflow solutions quickly without reinventing the plumbing. Your infrastructure should multiply the team's output.

Who You Are:

• 3+ years building software in production environments, with hands-on experience developing LLM-powered applications.
• You've built agents or agentic systems. You understand tool use, planning, evaluation, and the challenges of making AI reliable.
• Experience with document processing, embeddings, RAG, or knowledge graphs is a strong plus.
• Strong fundamentals in software engineering: you write clean code, design sensible systems, and ship consistently.
• Comfortable across the stack. Experience with our core technologies is a plus: Node.js, GraphQL, Postgres, React/Next.js.
• You think from first principles. You can navigate ambiguity, make tradeoff decisions, and figure out what to build when there's no playbook.
• You want ownership. You're excited by autonomy and accountability, not layers of process.

For candidates based in the United States, the expected pay 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. This role may also be eligible for additional variable compensation, including quota-based incentives where applicable. 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 may include equity
• Flexible paid time off
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA 
• Commuter Savings Account
• Human Interest: 401(k) provider
• Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
• Paid Holidays: Observance of all major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
• Collaborative, transparent, and fun culture