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 product, design, compliance, and customer support teams. Set technical direction for 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