Transportation Supervisor

Company: Loffredo Fresh Foods
Location: Madison
Posted on: February 15, 2026

Job Description:

Job Description Job Description Job Title: Transportation Supervisor Location: Deforest, WI Join Loffredo Fresh Foods as a Transportation Supervisor based out of our Deforest, WI Branch. We are a local, family-owned food and produce distributor that has proudly served the Midwest region for over 130 years. We distribute to 11 different states across our 6 locations. Loffredo Fresh Foods believes that our employees are the key to a successful future. We are committed to attracting a team that is passionate, innovative, and committed to meeting our customer’s needs. The Transportation Supervisor is responsible for leading and supporting the transportation team while ensuring efficient, safe, and timely delivery operations. This role oversees daily transportation activities including scheduling pickups, tracking shuttle movements, coordinating runbacks, managing trip reports, and maintaining accurate truck maintenance records. The supervisor serves as a hands-on leader by training and onboarding new drivers, participating in hiring decisions, operating delivery routes as needed, and acting as a backup for routing functions. Strong organization, communication, and problem-solving skills are essential to keep logistics running smoothly and to support continuous improvement within the transportation department. Pay: $58,000 - $65,000 annually What we look for: Class A CDL with a strong understanding of transportation and delivery operations 1–2 years of supervisory or leadership experience in transportation or logistics Highly organized with strong time management and planning skills Self-motivated and capable of working independently with minimal supervision Clear, professional verbal and written communication skills Advanced working knowledge of Microsoft Office, especially Excel Detail-oriented with strong problem-solving and decision-making abilities Dependable, flexible, and able to adapt to changing priorities Team-focused leader who thrives in fast-paced, high-pressure environments Demonstrates integrity, accountability, and a continuous improvement mindset What you’ll do: Lead, support, and motivate the transportation team to ensure safe, efficient daily operations Schedule weekly pickups and coordinate shuttle truck arrivals and departures Maintain and update truck maintenance records and transportation documentation Manage trip reports, runbacks, and driver paperwork to ensure accuracy and compliance Train, onboard, and support new drivers, including hands-on route assistance as needed Participate in interviewing, hiring, and ongoing development of transportation team members Operate delivery routes when necessary and serve as a backup for routing functions Communicate effectively with drivers, leadership, and cross-functional teams to resolve issues Identify opportunities for process improvements and operational efficiencies Benefits: Competitive salary and comprehensive benefit package including medical, dental, vision, available 1st of the month following 30 days employment 401k with company match available following 6 months of employment Additional voluntary insurance such as basic/supplemental life and disability Paid time off & Paid holidays Regular and constructive performance feedback Healthy, fresh produce you can take home to your family through our generous employee purchase program

Keywords: Loffredo Fresh Foods, Kenosha , Transportation Supervisor, Logistics, Transportation & Drivers , Madison, Wisconsin