Transportation Supervisor

About the Role

Charlie's Produce Oregon Division is seeking a Transportation Supervisor who is passionate about supporting drivers and keeping our wheels turning smoothly. Being a 24/7 deadline-driven industry, top candidates should possess a strong sense of urgency, along with a high aptitude for problem-solving, work ethic, and the ability to pivot quickly to meet organizational and customer needs. With over 45 years' experience delivering nourishment to communities across the West Coast, Charlie's Produce is a leading produce distributor to restaurants, grocery stores, institutions, and wholesalers. As the Transportation Supervisor, you'll assist the Transportation Manager in ensuring safe, efficient, and timely deliveries while maintaining compliance with local, state, and federal regulations. This role is all about teamwork—providing guidance to drivers, solving problems on the fly, and helping uphold our high safety standards.

Who We Are

Charlie's Produce is the largest privately owned produce wholesaler on the West Coast, and we are growing. The secret to our success in this industry is PEOPLE! We strive to hire the best and we reward them with a working environment that fosters loyalty, stability, innovation, and growth. Charlie's was founded in quality, and we are proud that it is still our focus. With a team of dedicated people who are passionate about food, supply chain, and their community we are looking for like minded individuals to help further our goal to enhance our communities through quality produce.

What We Offer

• An amazing company culture
• Medical/Dental/Vision coverage on the first of the month following hire
• ESOP (Profit Sharing) and 401(k)
• Paid vacations, sick time, and holidays
• Pre-tax commuter benefits, and onsite parking
• 100% Prepaid College Tuition for employees and their dependents
• Employee assistance program (EAP)

Responsibilities

• Technology Integration: Maintain awareness of transportation technologies and systems. Evaluate and recommend new tools that can improve operations, assist with implementation and training efforts for adopted technologies.
• Safety Coordination & Compliance: Investigate safety complaints, coordinate driver safety meetings, and stay updated on industry best practices to promote a culture of safety. Maintain compliance with company safety standards and ensure all drivers comply with DOT, FMCSA, and state regulations.
• Scheduling & Route Optimization: Assist with scheduling, dispatching, and route/backhaul coordination to ensure timely deliveries while maximizing route profitability. Utilize technology and knowledge of delivery areas to optimize routes and improve overall efficiency.
• Team Support: Work closely with the Transportation Manager to supervise and lead our fleet of drivers. Provide training, coaching, and guidance to ensure smooth operations and foster continuous improvement within the team.
• Problem-Solving: Serve as a primary resource for drivers, resolve delivery issues, and address customer concerns promptly. Maintain a customer service-driven approach while balancing company interests and driver needs.
• Team Engagement: Promote teamwork, accountability, and a safety-first mindset within the transportation department. Organize team-building activities and recognition programs to boost morale and retention.

Requirements

• Must be willing to work weekends and holidays to meet business needs.
• At least three (3) years of experience in transportation or logistics.
• At least two (2) years in a supervisory or leadership position.
• Strong verbal and written communication skills, must be able to work effectively with drivers, internal teams, and external partners.
• A customer-focused, solutions-oriented approach to problem-solving.
• Ability to adapt and thrive in a fast-paced environment.
• Familiarity with state and federal transportation regulations; knowledge of FMCSA, DOT, and Oregon requirements a plus.
• Proficiency in Microsoft Office applications (Outlook, Excel, Word, PowerPoint).

Qualifications

• For insurance purposes, a current driver's license, DOT medical card, and acceptable driving record is strongly preferred.
• CDL Class A or B preferred but not required.