Staff Software Engineer, AI Enablement

OhioX; Northern (KY); On-site; USD 189,000 - 265,000; Full time

Job summary

Root is hiring a Staff Software Engineer for the AI Enablement Squad to set cross-team direction on leveraging AI in real workflows and to drive reusable capabilities for the AI Platform. You will lead initiatives connecting real-world needs to platform strategy while mentoring engineers and collaborating with senior leaders.

Ideal candidates have 7+ years as a software engineer, 3+ years of leadership, and deep fluency with AI tools and platform patterns, with a track record of delivering

Qualifications

• 7+ years as a software engineer.
• 3+ years leading software teams or major technical initiatives.
• Ability to set technical direction and deliver results across multiple teams or a meaningful functional domain.
• Deep fluency with AI tools, technologies, and application patterns.
• Strong product, systems-thinking, and problem-framing skills in ambiguous, cross-functional environments.

Responsibilities

• Define how Root discovers, adopts, and scales AI-native ways of working across teams.
• Lead strategic embedded engagements aligning company priorities, real workflows, and reusable capabilities.
• Turn patterns from the field into platform strategy, architecture, and investments.
• Design scalable engagement and adoption models to accelerate learning across teams.
• Align engineering and business leaders on opportunities, tradeoffs, outcomes, and responsible practices.
• Unblock multi-team initiatives and establish measurable AI adoption impact.
• Mentor engineers and technical leaders with systems thinking and user-centered leadership.

Skills

Software engineering

Leadership

AI tools

Cross-functional collaboration

Strategy & direction

Communicate complex AI concepts

Mentorship

Stakeholder alignment

Job 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. 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

AI Enablement Squad is Root’s team for helping people across the company learn how to use AI in their real workflows, turning what they learn into improvements to the AI Platform, and contributing directly to building and shipping those capabilities. As a Staff Software Engineer on AI Enablement Squad, you will set cross-team direction for how Root learns to work with AI, connect the needs uncovered in real workflows to AI Platform strategy, and lead the initiatives that turn local learning into reusable company capabilities.

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

• Define how Root discovers, adopts, and scales AI-native ways of working—and make that approach practical across teams.
• Lead strategic embedded engagements that connect company priorities, real user workflows, and the reusable capabilities AI Platform should build next.
• Turn patterns from the field into platform strategy, architecture, and technical investments that create compounding value rather than one-off wins.
• Design scalable engagement and adoption models that help more teams learn faster while reducing repeated effort.
• Align engineering and business leaders on the opportunities, tradeoffs, outcomes, and responsible practices that matter most.
• Unblock multi-team initiatives and establish clear ways to measure whether AI adoption is changing how Root works for the better.
• Develop engineers and technical leaders through mentorship, systems thinking, and a clear example of user-centered technical leadership.

What You Will Need to Succeed

• 7+ years as a software engineer
• 3+ years leading software teams or major technical initiatives
• Demonstrated ability to set technical direction and deliver results across multiple teams or a meaningful functional domain.
• Deep fluency with AI tools, technologies, and application patterns, including judgment about responsible and scalable use.
• Strong product, systems-thinking, and problem-framing skills in ambiguous, cross-functional environments.
• Experience turning user needs and experiments into reusable products, platforms, or operating models.
• Ability to align senior stakeholders, drive cross-team decisions, and communicate complex AI concepts clearly.
• A record of identifying strategic technical investments, unblocking large initiatives, and developing engineers beyond an immediate team.
• Excellent collaboration and influence skills with technical and non-technical leaders.

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 [e-mail].