Staff Software Engineer - 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. Root's Engineering team is committed to building a flexible platform on which our product designers and quantitative scientists can quickly test ideas, deploy them into production, and iterate, with the ultimate objective of a delightful customer experience coupled with effective risk management.

The Opportunity

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.

Salary Range: $188,800 - $265,000 (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

• 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.

What You Will Need to Succeed

• 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.

As 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.

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Consistent 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. If reasonable accommodation is needed, please contact [email protected].