Head of Engineering

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

We are seeking a Head of Engineering to lead and scale a high-performing engineering organization. Reporting to the President & CTO, this is a critical executive role responsible for aligning technology strategy with business goals, driving execution, and building a high-performance engineering culture.

You will be responsible for setting and executing a bold multi-year technical vision, driving operational excellence, and partnering cross-functionally to accelerate the pace of product delivery. We’re looking for a leader who combines strategic vision, technical depth, and outstanding communication with a deep care for team health, customer impact, and disciplined thinking.

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.

Salary Range: $300,000-450,000 (Also eligible for competitive bonus and equity offering)

How You Will Make an Impact

• Define, evangelize, and execute a multi-year technical vision that aligns with the long-term company strategy and inspires internal and external stakeholders.
• Establish and evolve a talent strategy that attracts, develops, and retains top-tier engineering talent at all levels.
• Drive operational excellence through rigorous planning and measurement, effective incident management, and accelerated product velocity. 
• Lead capacity planning and organizational design to maximize engineering throughput and organizational health.
• Set and manage clear KPIs for engineering velocity, product quality, system reliability, and team health while demonstrating measurable progress over time.
• Serve as a key member of the senior leadership team, driving cross-functional alignment and influencing both tactical and strategic decisions. 
• Rigorously evaluate and adopt new technologies where strategically beneficial. 
• Ensure the security, scalability, and reliability of systems and infrastructure. 

What You Will Need to Succeed

• 5+ years of experience leading engineering teams of 100+ in a fast-paced, product-focused environment.
• 10+ years of industry experience, preferably in technology-first companies delivering direct-to-consumer customer experiences that leverage data science models as a fundamental component of the product. 
• A strong, practical technical foundation with the desire and skill to dig deep into architectural and technical challenges as needed.
• Demonstrated ability to develop, communicate, and deliver long-range technical strategy, with a strong record of execution.
• Passion for engineering operations and excellence in areas like capacity planning, process design, measurement, and incident management.
• A proven track record of hiring and developing world-class engineering talent and leadership.
• Executive-level communication skills, with the ability to align stakeholders across technical and business domains.
• A deep appreciation for and track record of balancing product delivery with long-term technical investments.
• Experience supporting data science efforts through ML engineering and MLOps.
• Proven ability to evaluate, test, and integrate emerging technologies into large-scale, complex systems.

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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