Paratransit Trainer

WeDriveU • Chicago, IL

7d • Onsite

About The Position

The Paratransit Trainer owns operator training at CDT South, running the classroom and behind-the-wheel instruction that gets new drivers road-ready and keeps current operators current. The role sets the standard for safe, ADA-compliant paratransit service and works closely with Operations and Safety to close performance gaps as they surface.

Requirements

• High school diploma or equivalent required
• Valid driver's license appropriate to the vehicle class operated on the contract.
• Must pass pre-employment physical, medical, and substance-abuse screening, and is subject to random substance-abuse testing under company policy.
• Working knowledge of Google Workspace or Microsoft Office (Word, Excel, Outlook, PowerPoint) and transportation-related software.
• Strong classroom and group-presentation skills, with clear coaching and feedback for a driver workforce.
• Organized, able to manage multiple training cohorts and schedules at once.
• Sound judgment under pressure and a service-first response to unexpected events.

Nice To Haves

• Some college preferred.
• Three or more years in transportation training preferred, ideally in paratransit or demand-response service.
• Experience leading, coordinating, or mentoring a driver or trainer workforce preferred.
• Must complete WeDriveU's paratransit bus driver instructor certification; equivalent trainer experience may be substituted where appropriate.

Responsibilities

• Exercise independent judgment to lead, design, develop, and implement initial and recurrent training programs for paratransit operators, across both classroom and behind-the-wheel instruction.
• Assess and certify new operators as road-ready and confirm every operator stays current with company and contract training requirements.
• Supervise, direct, and schedule behind-the-wheel trainers and evaluators, set their objectives, and hold them accountable for consistent, standards-based instruction.
• Deliver classroom instruction to WeDriveU and client specifications, covering: Defensive driving and service-area familiarization. Passenger loading and unloading, including ADA-compliant securement, lifts, ramps, and wheelchair tie-downs. Manifest documentation and use of on-board equipment. Accident and emergency procedures. Dispatch and radio communication. Passenger assistance and sensitivity for riders with disabilities.
• Document all training activity and keep operator training records accurate and audit-ready.
• Provide ongoing coaching and performance evaluations, and partner with Operations to retrain operators flagged for safety or service concerns.
• Keep training materials, safety content, and job aids aligned with current company policy and contract requirements.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED