Transportation Manager

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

Transportation

Transportation Manager

$65,000.00 / year

Juneau

,

Ketchikan

The Role.

Lead our fleet of 25+ professional CDL drivers and keep every guest transfer safe, on-time, and full of Alaska hospitality. You’ll recruit, train, schedule, and inspire the transportation team while ensuring our buses, coaches, and vans are DOT-compliant and ready to roll on Alaska’s most scenic (and challenging) roads. Working closely with operations, customer service, and front-desk teams, you’re the key to seamless dock-to-tour connections and happy guests from the moment they step off the ship.

Key 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

Requirements

• 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

What We Offer

• Highly competitive pay +performance bonus
• Scheduled days off to explore Alaska’s wilderness
• Free or deeply discounted staff tours (whale watching, rafting, jeep adventures, etc.)
• Work in the most breathtaking office on earth - glacier views included

If you love leading a sharp team, know the rules inside-out, and want to spend your summer making sure every guest starts and ends their Alaska adventure with a smile, this is your seat behind the wheel.