Lead AI Engineer

About the position

Fleetworthy is redefining compliance, safety, and efficiency for fleets using AI. We're looking for a hands-on, technical AI engineer to help us build production-grade systems—starting with implementing AI across tolls, millions of documents and devices. This is a foundational role for our newly created AI platform team with visibility to the board. If you’re tired of building throwaway demos or chatbots, and you want to own systems that actually move revenue, safety, and customer trust, this is your role.

Responsibilities

• 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.

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.

Nice-to-haves

• Prior work in logistics, tolling, transportation, or regulated domains.