Supervisor, Transportation Services

Princess Cruises and Holland America Line; Anchorage (AK); On-site; USD 60,000 - 80,000; Full time

Benefits offered by this job

Travel - FREE CRUISE AFTER FIRST SEAS0

Referral Program

Experience – Of a lifetime!

Rewards & Incentives

Community Service

Employee Activities

Professional Growth

Job summary

Princess Cruises and Holland America Line seeks a Transportation Services Supervisor in Anchorage to lead the daily transportation operations, supervise a driver and dispatch team, and ensure safe, efficient guest and employee transport.

The role requires CDL Class B and DOT medical clearance, with 3+ years in operations or dispatch. This seasonal full-time position offers Alaska opportunities and a path to professional growth.

Qualifications

• 3+ years in operations, dispatch or training roles.
• Strong leadership and decision-making skills.
• Ability to enforce safety and regulatory compliance.
• Proven ability to work in a fast-paced, seasonal cruise environment.

Responsibilities

• Supervise transportation services team and daily activities.
• Coordinate driver schedules and dispatch duties.
• Monitor radio and telephone communications; assign tasks as needed.
• Investigate incidents and ensure policy compliance.

Skills

Leadership

Dispatch & operations coordination

Team management

Safety awareness

Customer service focus

Education

High school diploma or equivalent

Tools

CDL Class B

DOT medical/physical

Job description

Supervisor, Transportation Services

Department: Transportation

Employment Type: Seasonal - Full Time

Location: Anchorage Transportation and Guest Services

Description

Service Excellence. Performance. Integrity. Teamwork. Consistency. Innovation. Are you a skilled transportation professional with a passion for leading teams and delivering exceptional service? We're looking for a Transportation Services Supervisor to oversee the daily coordination of transportation operations and help keep our guests and employees moving safely and efficiently.

In this dynamic leadership role, you'll manage dispatch operations, coordinate driver schedules, monitor communications, and ensure seamless day-to-day transportation services. You'll provide guidance and support to team members, assign operational priorities, and promote compliance with all company policies, safety standards, and regulatory requirements.

The ideal candidate combines strong operational expertise with outstanding leadership and problem-solving skills to maintain a safe, efficient, and service-focused transportation environment.

Join our team and play a key role in creating smooth, safe, and memorable journeys through some of Alaska’s most spectacular destinations.

Responsibilities

• Supervises transportation services team and activities.
• Performs driver and dispatch duties.
• Assists with scheduling, transportation services activities and operations.
• Monitor radio and telephones to assist drivers and assign tasks as needed.
• Routinely applies knowledge of operations, company products and customer services to assist staff with routine questions.
• Performs incident investigation and reporting.
• Carries out management responsibilities in accordance with the Company’s policies, objectives and applicable government laws and regulations.
• Other duties as assigned.

Requirements

• Current, valid Commercial Driver's License (CDL), Class B with an air brake endorsement is required. (May be obtained through Company training course.)Three (3) years of experience in positions involving operations, dispatch, or training.
• Current, valid driver's license, with three (3) years clean driving record. Motor Vehicle Report (MVR) will be requested.
• Must meet Company's clean driver eligibility requirements.
• Must be certified as physically qualified through a Department of Transportation (DOT) physical and drug screen.
• Minimum age of 21 is required to hold a CDL.
• Motor coach driving experience is required.
• Three (3) years of experience in positions involving operations, dispatch, or training.
• Must pass a pre-employment background check.
• Must be eligible to work in the United States. Holland America-Princess is unable to sponsor or take over sponsorship of employment visas at this time (e.g., H-2B status).

Knowledge, Skills, & Abilities:

• Possess the ability to troubleshoot and problem solve with minimal supervision.
• Proficiency in the use of computer business applications.
• Ability to organize and prioritize work, maintain attention to time constraints, while working in a team or group environment.
• Ability to work in a fast-paced environment with multiple tasks and external influences.
• Ability to work independently with minimal supervision while achieving daily goals.
• Ability to support and comply with company policies, procedures and guidelines including support and comply with company health and safety standards.
• Ability to stand/walk/work on feet for minimum of 8 hours per day.

Benefits

• Travel - FREE CRUISE AFTER YOUR FIRST SEASON!
• Reward for Referral Program
• Experience – Of a lifetime!
• Rewards & Incentives
• Community Service
• Employee Activities
• Professional Growth

HAP Alaska Yukon is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin, disability or protected veteran status.