Job Description

Are you a strong leader who thrives in a fast-paced environment and enjoys coordinating people, schedules, and operations? We are seeking a Transportation Supervisor to oversee our transportation services and ensure safe, reliable transportation for the individuals we support across Connecticut and New York.

In this role, you'll lead a team of drivers and transportation aides, manage daily transportation operations, coordinate fleet maintenance, optimize routes, and serve as a key problem-solver for transportation-related needs.

What You'll Do

Lead Transportation Operations

• Oversee the day-to-day operations of the transportation department.
• Supervise, coach, mentor, and develop Transportation Drivers and Transportation Aides.
• Manage hiring, onboarding, training, scheduling, and performance management activities.
• Ensure adequate staffing coverage by coordinating schedules, vacations, call-outs, and leaves.
• Assign and dispatch drivers to routes and community locations.
• Respond to transportation emergencies, service disruptions, weather impacts, and schedule changes.
• Serve as the primary transportation resource for operational issues during business hours.

Manage Scheduling & Service Delivery

• Coordinate transportation schedules and route assignments across programs.
• Partner with Program Managers and agency leadership to ensure transportation needs are met.
• Continuously evaluate routes to maximize efficiency while maintaining excellent customer service.
• Adapt schedules based on individual needs, staffing changes, vehicle availability, and program requirements.

Support Driver Success

• Provide ongoing coaching, feedback, and performance evaluations.
• Ensure compliance with required agency, state, and regulatory training requirements.
• Maintain driver qualifications and certifications.
• Promote a culture of safety, accountability, and excellent customer service.

Oversee Fleet Operations

• Coordinate vehicle maintenance, inspections, repairs, registrations, and vendor appointments.
• Monitor fleet utilization and recommend improvements to increase efficiency.
• Ensure all agency vehicles remain compliant with transportation regulations in Connecticut and New York.
• Work closely with maintenance vendors to minimize vehicle downtime.

Utilize Transportation Technology

• Manage transportation data and records using systems such as Salesforce, Evolv, Azuga, and UKG Pro.
• Monitor GPS and driver safety technology.
• Analyze transportation trends, vehicle usage, operational metrics, and safety data.
• Identify opportunities to improve efficiency and reduce operating costs.

Be a Communication Hub

• Build strong partnerships with individuals served, families, guardians, staff, schools, vendors, and community partners.
• Communicate transportation updates, delays, and service changes promptly and professionally.
• Address concerns proactively and escalate issues when appropriate.

Step In When Needed

• Maintain required driving credentials and endorsements.
• Serve as a backup driver when operational needs require additional coverage.

What We're Looking For

• High School Diploma or equivalent required; Associate's or Bachelor's degree preferred.
• Valid driver's license with a satisfactory driving record.
• Ability to obtain and maintain Connecticut PPEC and V endorsements.
• Ability to meet all applicable Federal DOT requirements.
• Reliable personal vehicle and required insurance coverage.
• Previous supervisory experience preferred.
• Experience in transportation operations, dispatching, scheduling, logistics, fleet management, or a related field preferred.
• Strong leadership, communication, organization, and problem-solving skills.
• Ability to make sound decisions in a fast-moving environment while balancing multiple priorities.