LEEO is on a mission to make roads safer—one fleet at a time. We’re transforming commercial auto insurance with AI and data-driven insights, offering options that reward safe driving and improve outcomes for fleets.

We are seeking a Head of Engineering to lead the strategy, architecture, and execution of the backend systems that power our core insurance and operational workflows. This role is responsible for scaling high-performing Python services, driving enterprise system integrations, and ensuring our platform is secure, reliable, and built for growth.

You will provide technical leadership across backend services, APIs, integrations, and cloud infrastructure—guiding the evolution of our architecture as we expand our capabilities and customer base.

Responsibilities

• Own the backend engineering strategy, architecture, and roadmap aligned with business objectives.
• Lead the design, development, and scaling of backend services and APIs using Python.
• Architect and oversee microservices that integrate core insurance platforms, internal systems, and third-party services.
• Provide technical leadership for enterprise system implementations, including configuration, integration, and workflow automation.
• Drive the development of middleware and API layers enabling seamless data exchange across distributed systems.
• Oversee backend automation and data processing workflows supporting underwriting, claims, billing, and reporting operations.
• Translate business and regulatory requirements into scalable, secure, and compliant technical solutions.
• Guide architectural decisions, platform modernization initiatives, and performance optimization efforts.
• Establish and enforce cloud-native best practices using AWS, including CI/CD pipelines, infrastructure-as-code, monitoring, and security standards.
• Set and maintain high standards for code quality, testing, observability, and system reliability.
• Lead incident response, production troubleshooting, and system performance optimization across environments.
• Mentor and grow backend engineering talent, fostering a culture of technical excellence and ownership.

Skills and Qualifications

• Extensive backend engineering experience with Python as a primary language.
• Proven experience architecting and scaling RESTful APIs, microservices, and distributed systems.
• Strong expertise in system integrations, data modeling, and backend architecture design.
• Experience working with enterprise platforms (e.g., insurance core systems such as Guidewire or similar) is a plus.
• Proficiency with SQL and/or NoSQL databases.
• Deep experience with AWS services, CI/CD pipelines, and infrastructure-as-code practices.
• Strong understanding of integration patterns (event-driven systems, message queues, ETL processes).
• Experience leading engineering teams and driving technical strategy.
• Ability to operate effectively in fast-paced environments with evolving requirements.
• Excellent communication skills and ability to partner across technical and non-technical stakeholders.
• Experience in insurance or other regulated industries is a plus.

Location: Remote.