Head of Engineering

Root Insurance

94d • Remote

About The Position

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.

Requirements

• 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.

Responsibilities

• 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 This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees