About LEEO
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.
Position Overview
We are seeking a Vice President of Engineering – Insurance Services to lead the design, development, and delivery of LEEO’s insurance systems. This leader will oversee engineering across key insurance domains including underwriting, policy lifecycle management, and carrier integrations. The VP will drive the delivery of scalable insurance infrastructure while also configuring and orchestrating point solutions around LEEO's core technology to enhance flexibility, efficiency, and speed to market.
Responsibilities
- Lead engineering strategy and execution across insurance systems, including underwriting workflow, policy administration, rating, and carrier integrations.
- Leverage AI and machine learning technologies to enhance automation, predict risk trends, and drive intelligent decision-making across underwriting, reporting, and telematics workflows.
- Partner with Product, Data, and Operations teams to translate business goals into technical roadmaps for underwriting, telematics, and reporting initiatives.
- Oversee delivery of key initiatives including:
- Underwriting Workflow Platform – enabling automated risk evaluation and policy lifecycle efficiency.
- Reporting – building carrier reporting and compliance pipelines.
- Mobile Telematics Integration – developing data ingestion and processing systems for connected driver products.
- Configure and integrate modular point solutions (e.g., policy admin, document management, and compliance tools) with Fairmatic’s core technology stack, ensuring seamless interoperability across systems.
- Define and maintain architectural standards that enable scalability while supporting third-party integrations and evolving business needs.
- Drive modernization of infrastructure and software architecture using AWS, Python, and React, with a focus on security, automation, and performance.
- Experience implementing or integrating AI and ML-based solutions within enterprise or insurance technology environments.
- Introduce best practices for code quality, CI/CD, observability, and documentation within a fast-paced, startup environment.
Skills And Qualifications
- Proven experience architecting and scaling insurance or financial systems, including underwriting, policy, or data management platforms.
- Demonstrated ability to configure and integrate third-party point solutions around a core technology stack to extend system capabilities.
- Expertise in AWS, Python, React, and modern API-driven microservice architectures.
- Strong understanding of integrations, enterprise software, and regulatory or carrier ecosystems.
- Experience leading distributed, global engineering teams across multiple time zones.
- Strategic and hands-on leader capable of balancing architectural vision with delivery execution.
- Excellent communication, stakeholder management, and cross-functional collaboration skills.
- Startup, insurtech, or regulated industry experience strongly preferred.
Location
Remote
