Lead AI Engineer

Summary

Join Fleetworthy, a leading provider of fleet safety, compliance, and toll management solutions, as a hands-on AI Engineer. Build and own core AI infrastructure, including the feature store, model CI/CD, evaluation harnesses, and observability stack. Write and ship production code daily using Python, Go, and TypeScript. Architect and scale core components of the AI/data infrastructure. Collaborate with cross-functional teams and provide technical direction to engineers, vendors, and contractors. Present your roadmap and results to executives and the board. This role offers the opportunity to work on mission-critical AI systems that directly impact revenue, safety, and compliance, leveraging a vast dataset of toll, inspection, safety, and vehicle data.

Requirements

• 7+ years building backend or infrastructure systems, with 3+ years production experience in AI/ML
• Worked and built AI applications: we’ve built MCP servers, LangChain, RAG
• Experience with LLMs, computer vision, or real-time event processing
• Strong system design and technical leadership skills
• Ability to move fast in ambiguity, and bias toward delivering working software

Responsibilities

• Build and own the feature store, model CI/CD, evaluation harnesses, and observability stack across all AI efforts
• Write and ship production code daily (Python, Go, TypeScript)
• Architect and scale core components of our AI/data infrastructure
• Collaborate cross-functionally with product, design, compliance, and customer support
• Set technical direction for other engineers, vendors, and contractors
• Present your roadmap and results directly to executives and the board

Preferred Qualifications

Bonus: prior work in logistics, tolling, transportation, or regulated domains