TELECOMMUTE Lead Software Engineer, AI Enablement

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 Lead Software Engineer on AI Enablement Squad, you will guide the team’s portfolio of engagements, set quarterly priorities, and coach engineers as they turn field learning into platform improvements that create compounding value across Root.

Salary Range: $164,200 - $240,000 (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

• Shape a quarterly portfolio of embedded engagements that helps Root teams adopt AI where it can create the most meaningful leverage.
• Guide the team from workflow discovery and platform learning through clear requirements and reusable AI Platform improvements.
• Protect capacity for the work that compounds: reusable capabilities, adoption patterns, and the team practices that make them stick.
• Connect AI Platform, product engineering, data, security, and business partners around the opportunities that deserve shared investment.
• Create repeatable engagement models and playbooks that make successful AI adoption easier for each new team.
• Coach engineers to pair technical judgment with curiosity, empathy, and crisp communication about complex AI concepts.
• Make the team’s outcomes visible, helping stakeholders understand where adoption is working, what is blocking it, and what to do next.

• 5+ years as a software engineer
• 1+ years leading software teams or major technical initiatives
• Demonstrated ability to lead team-level delivery of customer-facing or internal technical solutions.
• Fluency with AI tools and technologies, plus practical judgment about responsible deployment and adoption.
• Strong product instincts: able to evaluate opportunities, define success, and make tradeoffs within a quarter.
• Experience working directly with varied users and influencing partners toward better workflows and outcomes.
• Ability to coordinate multiple engagements and cross-team dependencies while protecting focus and capacity.
• A coaching mindset and track record of helping teammates improve their technical and collaborative practice.
• Clear written and verbal communication that creates shared context with team members and stakeholders.