Transportation Supervisor

Island Time Watersports Caribbean Llc; Charlotte Amalie (United States Virgin Islands); On-site; USD 55,000 - 75,000; Full time

Job summary

RED Car USVI is seeking a Transportation Supervisor to support scheduling, dispatching, and ground logistics for USVI operations. The role requires coordinating with the Transportation Manager, DMC teams, and drivers to ensure accurate bookings and smooth transfers for guests and groups.

The candidate will handle weekly scheduling, vendor coordination, and reconciliation tasks while maintaining a proactive, inclusive team culture in a dynamic environment.

Qualifications

• Scheduling and dispatching responsibilities
• Strong communication and teamwork
• Attention to detail and data accuracy
• Ability to work independently and in a team environment
• Knowledge of local traffic laws (preferred)
• Experience with ground transportation coordination
• Experience with vendor coordination and invoicing

Responsibilities

• Create the weekly schedule for dispatchers, drivers, and vehicles.
• Load the schedule into Paycom.
• Assign drivers and vehicles to trips per schedule.
• Review next day bookings and ensure accuracy.
• Confirm assignments in the Red Transportation channel.
• Coordinate group movements with DMC team and airport arrivals/departures.
• Drive vehicles and provide ground support as needed.
• Reconcile charges and invoices; monitor bookings for accuracy.

Skills

TripWorks proficiency

Paycom

FareHarbor

Scheduling

Dispatching

Communication

Attention to detail

Independent work

Team collaboration

Local traffic laws knowledge

Tools

TripWorks

Paycom

FareHarbor

Job description

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 SupportAssist 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 & OperationsCreate 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 & AccountingReview 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 & CultureCreate a positive culture of inclusion and support between the transportation team.Communicate effectively and respectfully with the Call Center, team members, vendors, and guests.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 EnvironmentThis role may require a combination of office-based administrative work and occasional on-site support for ground logistics and driving/dispatching duties.