Lead AI Engineer

Bestpass - Fleetworthy; Canada; Remote; CAD 100,000 - 130,000; Full time

Job summary

A leading fleet management company in Canada is seeking a hands-on AI engineer to build production-grade systems across AI applications. With 7+ years of experience, you will actively contribute to core infrastructure that drives efficiency and compliance for fleets. This role promises impactful work with significant visibility to executives. Join an innovative team committed to making a difference in fleet safety and management.

Benefits

Competitive salary

Inclusive environment

Growth opportunities

Qualifications

• 7+ years building backend or infrastructure systems.
• 3+ years production experience in AI/ML.
• Experience with LLMs or real-time event processing.

Responsibilities

• Write and ship production code daily.
• Architect and scale core components of AI/data infrastructure.
• Present roadmap and results directly to executives.

Skills

Backend development

AI/ML production experience

System design

Technical leadership

Tools

Python

Go

TypeScript

MLFlow

LangChain

Job description

Overview

In September 2024, Bestpass, Fleetworthy, ExpressTruckTax and Drivewyze rebranded as Fleetworthy. This rebrand reflects our mission to simplify fleet safety, compliance, and toll management under one unified brand. Fleetworthy is revolutionizing road safety and fleet management with a command center for safety, compliance, and efficiency. Our connected suite provides real-time insights and control to maximize efficiency, reduce risk, and save money. With technology that unifies safety, compliance, toll management, weigh station bypass, and more, Fleetworthy empowers organizations to perform at their best. We simplify operations to ensure every vehicle and driver is not just compliant, but beyond compliant. Supporting millions of drivers and vehicles, Fleetworthy is leading a new era in road safety and fleet technology.

At Fleetworthy, you’re in the driver’s seat!

About the Role

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.

What You’ll Build

• Core AI Infrastructure: Build and own the feature store, model CI/CD, evaluation harnesses, and observability stack across all AI efforts.

You Will

• 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.

Why This Role Is Different

• Your models ship into real systems that affect revenue, safety, and compliance—not just vanity demos.
• You’ll work with a defensible data moat: 10+ years of toll, inspection, safety, and vehicle data across all 50 states.
• Your work will support fleets who carry everything from food to fuel—this is mission-critical AI.

What We’re Looking For

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

Our Stack

• Python, Go, TypeScript
• MLFlow, dbt, Dagster, LangChain, Triton Inference Server

What Drives Us to Work Every Day

• We pride ourselves on making a difference, for our employees, clients, and their businesses.
• We accept team members for who they are and what they bring to the table.
• We are proud to build all our relationships based on transparency and trust.
• We are a team of energetic and curious individuals passionate about the work we do every day!

Our Core Values – We are 1TEAM

• People 1st - People 1st! We win as a team by collaborating, having each other’s backs, and bringing out the best in each other. We always treat others as they would like to be treated.
• Trust - We inspire trust by delivering on our promises, owning outcomes, being transparent in our communications, and acting with integrity.
• Every Trip Matters - Because every trip that our customers take is important to them, it\'s important to us. Whether it is a load being hauled across the country or a service vehicle traveling on a toll road, our customers count on us to deliver the right expertise, software, and data to make every trip safe, efficient, and productive.
• Always Innovating - We solve for the customer and focus on outcomes. We are nimble in our approach. When we fail, we fail fast and learn from it. We are here to disrupt, not to fit in.
• Mindset - We are committed to a growth mindset. Our efforts and attitudes are what determine our abilities. We embrace good criticism. We seek new challenges. We never stop learning.

About Bestpass

Bestpass is a comprehensive payment platform provider and leader in toll management solutions for commercial fleets of all sizes. Bestpass saves fleets time and money by consolidating payments and providing insight into cost per vehicle. Bestpass, founded in 2001, covers 100% of major toll roads across the U.S., supports more than 30,000 customers, and processes over $1.5 billion in toll transactions annually. Bestpass offers a range of toll coverage options for owner-operators, regional fleets, and national fleets, as well as customized solutions for specific needs.

About Fleetworthy Solutions

Fleetworthy Solutions, Inc. provides DOT safety and regulatory compliance services to commercial fleets that take them Beyond Compliant. Fleetworthy combines exceptional client service, advanced technologies, and more than 40 years of transportation industry expertise to make sure that drivers and assets are truly fleetworthy. The company helps private fleets, for-hire carriers and third-party logistics companies of all sizes surpass compliance of federal, state, and local regulations and streamline processes to reduce costs and mitigate risks.

Equal Employment Opportunity

Fleetworthy is an equal opportunity employer. We value diversity and are committed to creating an inclusive environment for all employees.