Transportation Supervisor

Food Authority, INC; Westborough (MA); On-site; USD 70,000 - 90,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

401(k) with excellent company match

Paid time off

Opportunities for career advancement

Job summary

Food Authority, INC in Westborough, Massachusetts is seeking a Transportation Supervisor to oversee transportation operations, ensuring safety and compliance. This role involves leading a team, monitoring transportation performance, and maintaining high service levels in delivering food products.

The ideal candidate has proven experience in fleet operations and strong leadership skills, capable of working flexible schedules, including weekends and holidays. Benefits include competitive salary, insurance, and opportunities for advancement.

Qualifications

• Proven experience in transportation or fleet operations, with supervisory experience.
• Strong leadership and team-building skills.
• Ability to work flexible schedules including nights and weekends.

Responsibilities

• Plan, coordinate, and monitor transportation routes.
• Supervise daily transportation operations and driver activities.
• Ensure compliance with DOT regulations and safety standards.

Skills

Leadership

Communication

Organizational Skills

Problem-Solving

Bilingual (Spanish)

Tools

Transportation Management Systems (TMS)

Microsoft Word

Microsoft Excel

GPS

Job description

Position Summary

The Transportation Supervisor is responsible for exceeding customer service expectations by ensuring the safe, timely, and compliant transportation of food products to customer locations. This role oversees daily transportation operations, supervises drivers and helpers, ensures temperature‑controlled and undamaged deliveries, maintains FIFO inventory practices at customer locations, and enforces company policies and DOT regulations. This position plays a critical role in fleet performance, driver development, customer satisfaction, and safety.

Key Responsibilities

• Plan, coordinate, dispatch, and monitor transportation routes while ensuring compliance with DOT regulations
• Supervise daily transportation operations, including drivers and driver helpers
• Oversee fleet maintenance, inspections, and repairs to ensure vehicle safety and minimize downtime
• Monitor fuel usage, mileage, and operational performance metrics to optimize efficiency
• Manage transportation equipment and coordinate with vendors such as Ryder and Penske
• Lead driver onboarding and ongoing training, including CDL compliance and safety programs
• Facilitate annual and recurring training (e.g., Samsara, ELD, defensive driving, refrigeration, liftgate, visibility, accident protocols)
• Audit DVIRs and delivery practices regularly and coach employees based on performance trends
• Ensure full DOT compliance, including HOS, qualification files, drug and alcohol testing, and safety documentation
• Investigate accidents, incidents, and near misses; implement corrective and preventative actions
• Promote and maintain a strong safety culture and actively participate in safety committees
• Monitor KPIs such as on‐time delivery, vehicle utilization, and driver productivity
• Prepare and review operational reports to support data‑driven decision‑making
• Liaise with stores, customers, drivers, and vendors to resolve transportation issues and maintain high service levels
• Debrief drivers’ post‑route and manage documentation and tracking systems
• Provide route coverage as needed in emergency situations and perform duties in accordance with SOPs and company policies

Qualifications & Requirements

• Proven experience in transportation or fleet operations, with demonstrated success in a supervisory or leadership role
• Strong leadership, communication, and team‑building skills with the ability to motivate and influence a diverse workforce
• Highly organized with excellent attention to detail, particularly in training and operational execution
• Proficiency with Transportation Management Systems (TMS), routing software, GPS, and related technologies
• Strong computer skills, including Microsoft Word and Excel, and familiarity with scanning tools
• Excellent problem‑solving, decision‑making, and multitasking abilities in a fast‑paced environment
• Thorough understanding of DOT regulations, safety standards, and compliance requirements
• Bilingual (Spanish) skills is a plus
• Ability to work flexible schedules, including evenings, weekends, holidays, and overnight shifts (including Friday and Sunday nights)

Benefits

• Competitive salary commensurate with experience
• Opportunities for career advancement
• Medical, dental, and vision insurance
• Paid time off
• 401(k) with an excellent company match

We are an Equal Employment Opportunity Employer: Race, Religion, Color, National Origin, Citizenship, Sex, Age, Disability, Ancestry, Veteran Status, Genetic Information. In addition to federal law requirements, the Food Authority complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities.