{"id":164620,"url":"https://alion.io/job/root-insurance-engineering-manager-ii-ai-systems","title":"Engineering Manager II, AI Systems","company":{"id":58633,"name":"Root Insurance","domain":"joinroot.com","url":"https://alion.io/company/root-insurance","size_band":"201-500","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Rippling","truth_index":{"grade":"A","score":94,"open_postings":7,"ghost_share":0,"stale_share":0.143,"repost_share":0.143,"time_to_fill_p50_days":44,"computed_at":"2026-11-03T05:54:40Z"}},"role":"Leadership","role_family":"Leadership","seniority":"lead","employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":null,"hiring_geo_confidence":"structured","locations":[],"countries":[],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":188000,"max":259710,"currency":"USD","period":"year","gross":null,"usd_annual":259710},"salary_estimate":null,"experience_years_min":5,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"AI Agents","optional":false},{"name":"AWS","optional":false},{"name":"Prompt Engineering","optional":false},{"name":"RAG","optional":false}],"status":"live","first_seen_at":"2026-08-11T19:34:35Z","employer_posted_date":"2026-08-11","last_verified_at":"2026-11-03T05:01:23Z","board_verified":true,"closed_at":null,"days_open":83,"trust":{"level":"ok","repost_count":1,"flags":[],"days_open":83},"description":"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.\nThe Opportunity\nThe 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.\nSalary Range: $188,000 - $259,710 (Eligible for competitive bonus and equity offering)\nRoot 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.\nHow You Will Make an Impact\nLead 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\nPartner with business partners including product managers, data scientists, and quantitative scientists to define and execute the AI engineering roadmap\nEstablish engineering standards for AI system development including reliability, observability, security, and responsible AI practices\nManage 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\nIdentify gaps in the team and develop plans to address them through individual development, hiring, or cross-functional partnership\nEngage directly with code, design reviews, and technical challenges alongside your team when necessary, demonstrating a hands-on approach to problem-solving\nWork closely with the Engineering Leadership team to improve the effectiveness of the Engineering organization as a whole\nCoordinate across teams where AI infrastructure intersects with Platform, Data Platform, and product engineering to ensure seamless delivery\nWhat You Will Need to Succeed\n5+ years as a software engineer\n3+ years as a people manager on engineering teams\nExperience leading teams building AI/ML infrastructure, integrations, or developer tooling\nFamiliarity with large language model APIs, prompt engineering, retrieval-augmented generation, or AI agent frameworks\nProven ability to manage in ambiguity and drive execution on evolving technical strategy\nExcellent communication skills with engineering colleagues, data scientists, and senior business leaders\nExperience with cloud infrastructure (AWS preferred) and modern application development workflows\nAs part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.\nPlease see our Privacy Notice available HERE for more information on how we process your personal data.\nConsistent with the Americans with Disabilities Act (ADA) and the Civil Rights Act of 1964, it is the policy of Root to provide reasonable accommodation when requested by a qualified applicant or candidate with a disability, unless such accommodation would cause an undue hardship for Root. The policy regarding requests for reasonable accommodation applies to all aspects of the hiring process. 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