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 Applied AI Engineer to work directly alongside our risk advisors and turn their most time-consuming workflows into reliable AI-powered solutions. You'll be embedded with the team that serves our clients—understanding how they work, where they lose time, and what would make them dramatically more effective.

This isn't a platform engineering role. While our AI Agent Engineers build the core agent infrastructure, you'll operate on top of it—identifying specific workflow problems, designing AI solutions using LLMs and our internal tools, and shipping them into production. You'll own the full loop: problem discovery, solution design, implementation, and iteration based on real usage.

You need to be technical—comfortable writing production code and working with LLM APIs—but your superpower is translating messy, human workflows into clean, automated systems. You'll spend as much time understanding the problem as you do building the solution.

The surface area here is massive. Insurance runs on documents, emails, and expert judgment—exactly the kind of work LLMs are built to accelerate. You'll have the autonomy to find the highest-leverage opportunities and ship solutions fast.

What You'll Do:

Embed With the Business. Sit with our risk advisors. Learn how they manage policies, handle renewals, process claims, and communicate with clients and carriers. Understand where time goes, where errors happen, and where AI can make the biggest difference.
Build AI-Powered Workflow Solutions. 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.
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's actually working for the team.
Bridge Engineering and Operations. Be the connective tissue between our engineering team and our risk advisors. Translate operational pain points into technical requirements. Feed patterns you see in the field back to the agent platform team so they can build better infrastructure for everyone.

Who You Are:

3+ years building software in production environments, with hands-on experience applying LLMs to real-world problems.
You've built AI-powered solutions that real users depend on. You understand prompt engineering, LLM integration patterns, and the challenges of making AI reliable in production.
Strong software engineering fundamentals: 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.
High EQ and communication skills. You can sit with a non-technical team, understand their workflow deeply, and translate that into something you can build.
Bias toward action. You'd rather ship something imperfect and iterate than spend weeks designing the perfect system.
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

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Applied AI Engineer