Transportation Supervisor

The Transportation Supervisor plays a crucial role in ensuring the smooth and efficient operations of RED Car USVI. This position is responsible for a variety of administrative and logistical tasks, supporting the Transportation Manager and collaborating with other departments to maintain high standards of service and operational efficiency. He/she will assist with scheduling, reconciliation, and various ground-based logistics, while fostering a positive and inclusive team culture. 

Administrative Support 

• Assist in all transportation administrative needs, including private VIP transfers and requests from other departments or locations. 

• Ensure all charges are properly recorded and reconciled. 

• Support the cruise ship operation by ensuring updates are accurate in FareHarbor. 

• Report any employee or vendor issues to the Transportation Manager for follow-up. 

Scheduling & Operations 

• Create the weekly schedule for dispatchers, drivers, and vehicles by EOD on Thursday the week prior. 

• Load the schedule into Paycom. 

• Assign drivers and vehicles to trips in TripWorks based on the schedule. 

• Review all next day's bookings and assignments for accuracy the night before. 

• Confirm assignments in the Red Transportation Chat. 

• Collaborate with the DMC team on group guest movements, including airport meet and greets, hotel arrivals and departures, and activities as assigned by the Transportation Manager. 

• Drive vehicles and dispatch as assigned by the Transportation Manager. 

• Assist as assigned with any ground-based logistics in support of RED's USVI operations, which may include the movement of goods and/or associates. 

Reconciliation & Accounting 

• Review the underpaid report daily and follow up on collecting payment. 

• Cancel transient bookings with no payment if no payment is received within 24 hours. 

• Monitor the AMEX Buoy Haus program’s bookings for accuracy. 

• Ensure that all TripWorks driver assignments are accurate and that a driver and vehicle has been correctly assigned to each individual per booking. 

• Ensure that all DMC bookings are assigned appropriately. 

• Monitor upcoming transfers related to group travel and flag any issues to the Transportation Manager. 

• Track the status of DMC groups to ensure accuracy against the A&D. 

• Work with DMC coordinators to ensure that allocation is completed accurately. 

• Receive invoices from third-party vendors. 

• Reconcile trips in invoices to TripWorks for accuracy. 

• Send reconciliation to the Department Manager for final approval. 

• Compile a monthly report on Amex Usage for the Buoy Haus Amex program. 

• Send the monthly report to the Manager for final approval. 

• Bill the Buoy Haus Amex TripWorks Account once approved. 

• Send payment email to Buoy Haus for payment and follow up with the Buoy Haus team on payment. 

Communication & Culture 

• Create a positive culture of inclusion and support between the transportation team. 

• Communicate effectively and respectfully with the Call Center, team members, vendors, and guests. 

Qualifications

• Proficiency in using TripWorks software for booking and schedule management. 

• Strong organizational and time management skills. 

• Excellent communication and interpersonal skills. 

• Ability to work independently and as part of a team. 

• Attention to detail and accuracy in data entry and reconciliation. 

• Knowledge of local traffic laws and routes in St. Thomas, U.S. Virgin Islands (preferred). 

​​​​​​​​​​​​​​Work Environment 

• This role may require a combination of office-based administrative work and occasional on-site support for ground logistics and driving/dispatching duties.