TELECOMMUTE Engineering Manager II, AI Systems

Root is on a mission to unbreak insurance by creating experiences people love at prices they can’t believe. We believe that investing in world-class technology will facilitate a new class of insurance products, driving a massive positive impact on the hundreds of millions of drivers who carry auto insurance in the US.

The Opportunity

The Engineering Manager II, AI Systems leads Root’s AI Platform and AI Enablement Squad teams - the engineers responsible for building the infrastructure, tooling, and integrations that bring AI capabilities to life across Root’s product and operations. This is an early and high-visibility role: you will shape how Root builds AI-powered systems, establish engineering standards for responsible AI deployment, and grow a team of skilled engineers working on some of the most strategically important work at the company.

Salary Range: $188,000 - $250,000 (Eligible for competitive bonus and equity offering)

Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US.

How You Will Make an Impact

• Lead and grow the AI Platform and AI Enablement Squad engineering teams, responsible for the internal tooling, deployment patterns, and integrations that power Root’s AI features
• Partner with business partners including product managers, data scientists, and quantitative scientists to define and execute the AI engineering roadmap
• Establish engineering standards for AI system development including reliability, observability, security, and responsible AI practices
• Manage team members to ensure they are performing well individually and as a cohesive unit; use coaching, feedback, and delegation to achieve business and individual goals
• Identify gaps in the team and develop plans to address them through individual development, hiring, or cross-functional partnership
• Engage directly with code, design reviews, and technical challenges alongside your team when necessary, demonstrating a hands-on approach to problem-solving
• Work closely with the Engineering Leadership team to improve the effectiveness of the Engineering organization as a whole
• Coordinate across teams where AI infrastructure intersects with Platform, Data Platform, and product engineering to ensure seamless delivery

• 5+ years as a software engineer
• 3+ years as a people manager on engineering teams
• Experience leading teams building AI/ML infrastructure, integrations, or developer tooling
• Familiarity with large language model APIs, prompt engineering, retrieval-augmented generation, or AI agent frameworks
• Proven ability to manage in ambiguity and drive execution on evolving technical strategy
• Excellent communication skills with engineering colleagues, data scientists, and senior business leaders
• Experience with cloud infrastructure (AWS preferred) and modern application development workflows