Alaska Transportation Fleet Lead—Safe On-Time Shuttles

Holland America-Princess (Holland America Dawson City Inn); Juneau (AK); On-site; USD 58,500 - 71,500; Full time

Benefits offered by this job

Competitive pay

Performance bonus

Staff tours

Alaska wilderness access

Job summary

Holland America-Princess (Holland America Dawson City Inn) seeks a Transportation Manager in Alaska to lead 25+ CDL drivers and ensure safe, on-time guest transfers in Juneau and Ketchikan. You will recruit, train, schedule, and coach a DOT-compliant fleet, coordinating with operations and guest services to provide seamless dock-to-tour connections while upholding Alaska hospitality standards.

The role offers competitive pay, seasonal days off in Alaska’s wilderness, and staff tours; join a team

Qualifications

• Minimum 5 years commercial driving experience with Class B CDL + Passenger & Air Brake endorsements (Class A a plus).
• 2+ years in transportation supervision, fleet management, or lead driver/trainer role.
• Clean driving record and ability to pass DOT pre-employment screening.
• Current DOT Medical Card.
• Proven skills in team leadership, scheduling, and conflict resolution.
• Strong knowledge of FMCSA/DOT regulations and electronic logging devices.
• Excellent communication and guest-service mindset.
• Comfortable using scheduling software and basic computer systems.

Responsibilities

• Recruit, hire, and build a top-tier team of 25+ commercial drivers.
• Conduct pre-season and ongoing CDL training focused on defensive driving, guest interaction, narration basics, and Alaska-specific road protocols.
• Create and manage daily driver schedules and dispatch operations.
• Perform ride-alongs, driver evaluations, and continuous coaching.
• Ensure full compliance with DOT/FMCSA regulations, hours-of-service, vehicle inspections, and record-keeping.
• Oversee vehicle readiness in coordination with mechanics (pre/post-trip inspections, maintenance coordination).
• Maintain accurate driver files, certifications, drug/alcohol testing records, and vehicle logs.
• Foster a positive, professional, safety-first team culture.
• Handle on-season problem-solving for weather delays, traffic, or last-minute schedule changes.

Skills

Team leadership

Scheduling

Conflict resolution

DOT/FMCSA regulations

Guest service mindset

Tools

Scheduling software

Basic computer skills

Job description

Holland America-Princess (Holland America Dawson City Inn) seeks a Transportation Manager in Alaska to lead 25+ CDL drivers and ensure safe, on-time guest transfers in Juneau and Ketchikan. You will recruit, train, schedule, and coach a DOT-compliant fleet, coordinating with operations and guest services to provide seamless dock-to-tour connections while upholding Alaska hospitality standards.

The role offers competitive pay, seasonal days off in Alaska’s wilderness, and staff tours; join a team