Engineering Manager II, AI Systems

Root Insurance

58d•$188,000 - $259,710•Remote

About The Position

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.

Requirements

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

Responsibilities

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