Transportation Supervisor - Oak Creek, WI

Compass Group•Oak Creek, WI

About The Position

The Transportation Supervisor provides daily leadership to delivery drivers and logistics staff, ensuring safe, efficient, and accurate transportation operations. This role bridges strategic direction from the Manager with on‑the‑ground execution, supporting service quality, productivity, and DOT‑compliant operations across the fleet. The Supervisor ensures routes run smoothly, equipment is maintained, and drivers receive clear guidance and support.

Requirements

High school diploma or equivalent; logistics or transportation‑related training preferred.
Prior logistics or transportation lead/supervisory experience strongly preferred.
Strong communication, problem‑solving, and organizational skills.
Ability to make real‑time decisions in a fast‑paced, service‑driven environment.
Working knowledge of DOT regulations, routing tools, telematics systems, or fleet operations.

Responsibilities

Oversee daily routing, dispatching, and driver assignments to ensure on‑time, accurate deliveries.
Monitor route performance and adjust staffing or routes to meet operational demands.
Support real‑time problem solving, including route delays, equipment issues, or customer needs.
Ensure compliance with company policies, DOT regulations, and transportation safety standards.
Step in to drive routes when coverage or operational needs require it.
Lead, motivate, and support drivers through clear expectations, daily check‑ins, and consistent follow‑up.
Train new drivers on delivery processes, vehicle operation, DOT compliance, and customer service.
Provide coaching, counseling, and corrective action as needed, documenting concerns and partnering with the Manager on follow‑up.
Assist in evaluating driver performance and identifying development and training opportunities.
Serve as first‑line safety leader, ensuring all drivers follow safety policies and DOT requirements.
Conduct pre‑shift safety briefings, vehicle inspections, and compliance checks.
Report incidents, near misses, and hazards immediately; support incident reviews and root-cause investigations.
Maintain accurate records for DOT logs, DVIRs, and safety documentation.
Monitor delivery quality, accuracy, and customer satisfaction indicators.
Track route performance metrics (on‑time delivery, miles, stops, service failures) and escalate concerns.
Support continuous improvement efforts, implementing new processes or tools introduced by the Manager.
Act as the on‑shift point of contact for drivers, dispatch, warehouse teams, and customer service.
Communicate Manager‑level updates, priorities, and policy changes to staff clearly and consistently.
Provide timely feedback to the Manager about route performance, operational bottlenecks, and staffing needs.