This isn’t a “cool demo” role. You’ll build production-grade AI infrastructure that ships into real systems affecting revenue, safety, and compliance for fleets across North America. If you want ownership, board-level visibility, and work that actually matters, this is the lane.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and efficiency platform built to simplify how fleets manage safety, tolls, inspections, and vehicle data under one unified brand. They’re building AI-native products using a deep data moat from 10+ years of toll, inspection, safety, and fleet telemetry data across all 50 states. The goal is simple: help fleets operate safer, smarter, and beyond compliant.
Schedule
Canada-based remote or hybrid.
Foundational role on a newly created AI platform team with cross-functional collaboration.
Expectation: ship production code, build core AI infrastructure, and communicate progress to executive leadership.
What You’ll Do
Build and own core AI infrastructure including feature store, model CI/CD, evaluation harnesses, and observability across AI efforts
Write and ship production code daily (Python, Go, TypeScript) while architecting scalable AI and data systems
Partner across product, design, compliance, and support, guide technical direction for others, and present roadmap and results to executives and the board
What You Need
4+ years building backend or infrastructure systems plus 2+ years production experience in AI and ML
Experience delivering AI applications in real environments, including LLMs, RAG workflows, computer vision, or real-time event processing
Strong system design and technical leadership skills, comfort moving fast in ambiguity, and a bias toward shipping working software
Benefits
Remote or hybrid flexibility within Canada
Foundational ownership on an AI platform team with visibility to executives and the board
Modern stack: Python, Go, TypeScript, GCP and AWS, Postgres, Redis, Kafka, MLFlow, dbt, Dagster, LangChain, Triton Inference Server
This is a rare chance to build the core AI engine inside a company with real data, real customers, and real stakes. If you’re ready to ship AI that moves the needle, apply now.
Build it. Ship it. Prove it in production.
Happy Hunting,
~Two Chicks…