Transportation Supervisor

Red Hospitality & Leisure; Charlotte Amalie (United States Virgin Islands); On-site; USD 40,000 - 43,000; Full time

Job summary

Red Hospitality & Leisure seeks a Transportation Supervisor for USVI operations, overseeing administrative scheduling and ground logistics to support VIP transfers and cruise ship movements.

You will coordinate with dispatch, drivers, and vendors; manage reconciliations in FareHarbor/TripWorks/Paycom; and help maintain schedules and billing with accuracy and teamwork.

Qualifications

• Proficiency in TripWorks 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, USVI (preferred).

Responsibilities

• 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.
• 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.
• 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.
• 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.

Skills

TripWorks proficiency

Organizational skills

Communication skills

Interpersonal skills

Teamwork

Attention to detail

Local traffic laws (preferred)

Tools

TripWorks

Paycom

FareHarbor

Job description

Job DetailsJob Location: USVI Transportation - St. Thomas, US Virgin Islands 00802Salary Range: $20.00 - $20.00 HourlyTravel Percentage: NoneThe 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.