Paratransit Road Supervisor | Flexible Schedule, Benefits

WeDriveU; Chicago (IL); On-site; USD 30,000 - 43,000; Full time

Benefits offered by this job

Medical Insurance

401(k) with employer match

Paid holidays

PTO

Job summary

WeDriveU, Inc. in Chicago seeks a Road Supervisor to oversee field operations, ensuring safe, compliant bus operations and high service standards. The role requires CDL-P, strong communication, and hands-on leadership to coach operators and manage time-sensitive issues.

We operate 24/7 and offer competitive compensation and benefits. This full-time position provides opportunities for growth within a nationwide mobility provider.

Qualifications

• Hard requirements: CDL-P endorsement and open availability.
• Experience in operations management or transit preferred.

Responsibilities

• Supervise day-to-day operator activities to ensure safety and compliance.
• Provide guidance to operators to handle customer issues and safety concerns.
• Monitor on-time performance and prepare required reports.
• Maintain a positive work environment and coach staff.
• Ensure policy adherence and supervise DVIs audits.

Skills

Multitasking

Detail oriented

Excel (intermediate)

Interpersonal communication

Coaching & mentoring

Education

Commercial Driver's License with Passenger Endorsement

Tools

Microsoft Office Suite

Job description

WeDriveU, Inc. in Chicago seeks a Road Supervisor to oversee field operations, ensuring safe, compliant bus operations and high service standards. The role requires CDL-P, strong communication, and hands-on leadership to coach operators and manage time-sensitive issues.

We operate 24/7 and offer competitive compensation and benefits. This full-time position provides opportunities for growth within a nationwide mobility provider.