If you’re tired of building cute AI demos and want to ship real systems that touch revenue, safety, and compliance, this role is the real deal. You’ll help build Fleetworthy’s foundational AI platform, with massive datasets, board-level visibility, and production outcomes that actually matter.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and toll management command center built to simplify operations and reduce risk. In September 2024, Bestpass, Fleetworthy, ExpressTruckTax, and Drivewyze unified under the Fleetworthy name to deliver one connected suite for fleets and drivers.
Schedule
• Canada-based (remote or hybrid)
• Foundational role on a newly created AI platform team
• High-visibility work with executive and board-facing communication
What You’ll Do
⦁ Build and own core AI infrastructure: feature store, model CI/CD, evaluation harnesses, and observability across AI efforts
⦁ Write and ship production code daily using Python, Go, and TypeScript
⦁ Architect and scale core components of AI and data infrastructure
⦁ Implement AI into real business systems across tolls, documents, and devices at massive scale
⦁ Collaborate cross-functionally with product, design, compliance, and customer support
⦁ Set technical direction for other engineers, vendors, and contractors
⦁ Present roadmap, progress, and results directly to executives and the board
What You Need
⦁ 4+ years building backend or infrastructure systems, plus 2+ years production experience in AI/ML
⦁ Proven track record delivering AI applications (RAG, LangChain, MCP servers, or similar)
⦁ Experience with LLMs, computer vision, and/or real-time event processing
⦁ Strong system design and technical leadership skills
⦁ Bias toward shipping working software in ambiguous, fast-moving environments
⦁ Bonus: experience in logistics, tolling, transportation, or other regulated domains
Benefits
⦁ Work with a defensible data moat: 10+ years of toll, inspection, safety, and vehicle data across all 50 U.S. states
⦁ Build production AI that impacts safety, compliance, customer trust, and revenue
⦁ Modern stack: Python, Go, TypeScript, GCP/AWS, Postgres, Redis, Kafka, MLFlow, dbt, Dagster, LangChain, Triton Inference Server
⦁ Early seat on a platform transformation with real buy-in, budget, and ownership
If you’re qualified for this, don’t play small. These “foundational AI engineer” roles don’t sit open long.
If you want to own the backbone of a real AI platform and ship systems that move the business, this is your shot.
Happy Hunting,
~Two Chicks…