Staff Software Engineer, AI Systems

Root Insurance
•$188,800 - $265,000•Remote

About The Position

As a Staff Software Engineer focused on AI, you will help turn that ambition into trustworthy, useful capabilities across Root. You will set technical direction, lead work across teams, and connect the needs of people using AI in real workflows to the platforms and practices that support them. This role may emphasize foundational platform engineering or hands-on enablement and adoption, depending on your strengths and the work that needs to be done. The work spans two closely connected teams: AI Platform builds shared infrastructure, tooling, and operating patterns for reliable and secure AI; AI Enablement Squad partners with teams to apply AI in their workflows and turns those learnings into reusable capabilities. Your impact will extend beyond either team.

Requirements

  • 7+ years of software engineering experience and 3+ years leading software teams or major technical initiatives.
  • A record of setting technical direction and delivering results across multiple teams or a meaningful engineering domain.
  • Strong systems and product judgment: you can frame ambiguous problems, evaluate tradeoffs, and turn learning into reusable capabilities.
  • Experience with AI/LLM technologies and application patterns, with sound judgment about responsible, scalable use.
  • Depth in cloud/platform architecture and production operations, ideally including AWS, Terraform, and secure software delivery
  • Depth in hands-on AI enablement, user-centered problem discovery, and translating experiments into products or operating models
  • Ability to drive cross-team decisions, communicate complex ideas to senior technical and non-technical leaders, and develop engineers beyond your immediate team.

Responsibilities

  • Set a multi-quarter technical direction for how Root builds, adopts, and improves AI-enabled systems, balancing immediate opportunities with durable investments.
  • Lead cross-team initiatives from ambiguous problem framing through architecture, implementation, and measurable outcomes.
  • Connect real user workflows and experiments to shared services, platform strategy, and scalable ways of working rather than one-off solutions.
  • Make sound tradeoffs across security, responsible use, reliability, observability, cost, usability, and long-term maintainability.
  • Align engineering and business leaders on priorities and decisions; unblock work across product engineering, data, security, infrastructure, and other partners.
  • Establish feedback loops and measures that show whether AI capabilities are dependable and whether adoption improves how Root works.
  • Anticipate emerging constraints, shape technical investments, and multiply your impact by mentoring engineers and technical leaders.

Benefits

  • Eligible for competitive bonus and equity offering
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