Lead AI Engineer

Overview

Lead AI Engineer position at Bestpass by Fleetworthy. Fleetworthy is a rebrand of Bestpass, Fleetworthy, ExpressTruckTax and Drivewyze, merging safety, compliance and toll management under one brand. We are building a connected suite for real-time safety, compliance, toll management and efficiency, empowering organizations to maximize performance while maintaining high standards of safety and compliance.

About the Role : Fleetworthy is redefining compliance, safety, and efficiency for fleets using AI. We are 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 AI platform team with visibility to the board.

If you're tired of demos and want to own systems that move revenue, safety, and customer trust, this role is for you.

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

Why This Role Is Different

What We're Looking For

Our Stack

What Drives Us to Work Every Day

Our Core Values – We are 1TEAM

About Bestpass

Bestpass is a comprehensive payment platform provider and toll management leader for commercial fleets. Bestpass consolidates payments, provides cost insights, and supports thousands of customers with toll coverage across major roads in the U.S.

About Fleetworthy Solutions

Fleetworthy Solutions provides DOT safety and regulatory compliance services to commercial fleets, combining client service, technology, and transportation industry expertise to help drivers and assets stay compliant and reduce costs and risks.

Fleetworthy is committed to fostering a diverse and inclusive culture and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital status, pregnancy or maternity, gender identity or gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws.

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