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.