Transportation Operations Supervisor, Middlesex

The Transportation Operations Supervisor will lead day-to-day transportation activities.
This role is responsible for overseeing onsite dispatch operations, driver engagement, account management, compliance administration, fleet maintenance coordination, and supporting regional growth initiatives.
The Transportation Operations Supervisor is a leader who thrives in a fast-paced environment, builds strong relationships with drivers and customers, and can effectively balance operational execution with strategic growth responsibilities.
Key Responsibilities
Transportation Operations & Dispatch
Manage daily transportation and dispatch operations to ensure safe, efficient, and on-time service execution.
Maintain a strong onsite presence with dispatch operations, prioritizing face-to-face interaction with drivers and operational staff.
Coordinate load planning, routing, scheduling, and driver assignments to maximize operational efficiency and service levels.
Monitor transportation KPIs including on-time delivery, driver utilization, dwell time, safety performance, and customer satisfaction.
Partner closely with warehouse and transportation leadership to ensure seamless operational execution.
Driver Relations & Leadership
Serve as a primary operational contact for drivers and transportation personnel.
Foster a positive driver culture through direct communication, coaching, and problem resolution.
Support driver onboarding, training, scheduling, and retention initiatives.
Ensure compliance with company policies, DOT regulations, and safety standards.
Account Management & Customer Support
Act as the primary point of contact for existing transportation accounts and support new business opportunities transitioning into Romark operations.
Build and maintain strong customer relationships through proactive communication and operational responsiveness.
Collaborate with business development and operations teams to ensure successful customer onboarding and service implementation.
Assist with identifying operational improvements and growth opportunities within customer accounts.
Compliance & Clearinghouse Management
Oversee FMCSA Clearinghouse administration and compliance activities.
Coordinate and manage compliance programs utilizing JJ Keller and other transportation compliance platforms.
Ensure compliance with DOT regulations, driver qualification files, drug and alcohol program requirements, hours-of-service regulations, and safety standards.
Support audits, reporting requirements, and corrective action initiatives as needed.
Driver Payroll Administration
Manage and oversee driver payroll processing, ensuring accurate and timely compensation.
Review and validate driver hours, mileage, load pay, and other compensation components prior to payroll submission.
Coordinate with Human Resources and finance teams to resolve payroll discrepancies and ensure compliance with company pay policies.
Ensure payroll practices align with DOT regulations, wage and hour laws, and company policies.
Assist leadership with payroll reporting, labor tracking, and operational cost analysis related to transportation staffing.
Fleet Maintenance Coordination
Oversee trucking fleet maintenance scheduling and coordination to ensure equipment reliability and regulatory compliance.
Partner with maintenance vendors and internal teams to manage preventive maintenance programs, repairs, inspections, and equipment uptime.
Monitor maintenance expenses and assist with fleet optimization initiatives.
Ensure all equipment meets DOT safety and operational standards.
Regional Leadership & Growth
Assist with strategic planning, operational scaling, and regional expansion initiatives.
Drive operational consistency, process improvement, and leadership development across the region.
Collaborate cross-functionally with transportation leadership, operations, finance, HR, and customer teams.
Qualifications
Bachelor's degree in Supply Chain, Logistics, Business, or related field preferred; equivalent experience considered.
5+ years of transportation, dispatch, or fleet operations management experience.
Strong understanding of DOT, FMCSA, Clearinghouse, and transportation compliance requirements.
Experience with trucking maintenance coordination and fleet management.
Proven ability to manage customer relationships and transportation accounts.
Strong leadership, communication, and problem-solving skills.
Ability to work onsite in a fast-paced transportation environment.
Experience with TMS platforms, JJ Keller, ELD systems, and transportation technology preferred.