Paratransit Road Supervisor — 24/7 Operations Leader

WeDriveU; Chicago (IL); On-site; USD 75,000 - 110,000; Full time

Benefits offered by this job

Medical Insurance

401(k) with employer match

PTO

Paid holidays

Pet & Legal Insurance

Job summary

WeDriveU in Chicago seeks a Road Supervisor to lead field operations, ensure safe, reliable shuttle service, and coordinate between drivers and the General Manager. This role supports 24/7 operations year-round and requires strong communication and leadership to keep service on track.

Responsibilities include supervising operators, coaching, monitoring timeliness, and preparing reports while upholding company policies. CDL-P endorsement and open schedule are required for this role.

Qualifications

• Experience supervising field operators in transportation or similar setting.
• Strong communication and problem-solving abilities.
• Open availability for a 24/7 operation.

Responsibilities

• Supervises day-to-day activities of operators to ensure safety and efficiency.
• Provides guidance on customer issues, safety, and scheduling.
• Maintains a positive work environment through coaching and mentorship.
• Monitors on-time performance and submits reports timely.
• Ensures policy compliance and conducts regular performance reviews.
• Manages disciplinary actions as needed.

Skills

Multitasking

Detail-oriented

MS Office/Excel

Interpersonal skills

Customer service

Leadership

Education

Commercial Driver's License with Passenger Endorsement

Tools

Microsoft Office

Job description

WeDriveU in Chicago seeks a Road Supervisor to lead field operations, ensure safe, reliable shuttle service, and coordinate between drivers and the General Manager. This role supports 24/7 operations year-round and requires strong communication and leadership to keep service on track.

Responsibilities include supervising operators, coaching, monitoring timeliness, and preparing reports while upholding company policies. CDL-P endorsement and open schedule are required for this role.