Transportation Supervisor & Driver Lead

Winebow; Virginia; On-site; USD 70,000 - 80,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

AD&D

401k with company match

Paid time off

Job summary

Winebow seeks a Transportation Supervisor to oversee route delivery timeliness and driver coverage in a Virginia setting. You will supervise staff, manage payroll processes, and ensure DOT/FMCSA compliance while coordinating between drivers and sales teams.

The role requires 1 year of supervisory logistics experience, a valid driver’s license (CDL preferred), and 3–5 years as a truck driver. In-office schedule and a comprehensive benefits package accompany this position.

Qualifications

• High school diploma or GED required; additional education preferred.
• One year of supervisory experience in a logistics role.
• Valid driver’s license; CDL preferred.
• Three to five years of experience as truck driver.

Responsibilities

• Ensure all routes are delivered in a timely manner.
• Manage coverage of drivers, vacations, and absences.
• Monitor driver performance and report issues to Transportation Manager.
• Train staff on safety policies and procedures; improve processes for safety.
• Handle payroll submissions, vacation approvals, recruiting, and performance appraisals.
• Conduct driver audits and maintain fuel receipts.
• Maintain daily Error Log and liaise between drivers and sales.

Skills

Supervisory experience

Payroll processing

Staff training

DOT/FMCSA compliance

Education

High school diploma or GED

CDL preferred

Tools

MS Office

Job description

Winebow seeks a Transportation Supervisor to oversee route delivery timeliness and driver coverage in a Virginia setting. You will supervise staff, manage payroll processes, and ensure DOT/FMCSA compliance while coordinating between drivers and sales teams.

The role requires 1 year of supervisory logistics experience, a valid driver’s license (CDL preferred), and 3–5 years as a truck driver. In-office schedule and a comprehensive benefits package accompany this position.