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DRIVER SUPERVISOR / TRAINER

With the opening of our new 10-acre headquarters in Florida, Palmetto Yacht Management is continuing its strategic growth and strengthening its leadership team.

Palmetto Yacht Management is the 2nd largest family-owned vessel relocation company in the industry, and we are seeking an experienced Driver Supervisor / Trainer to lead, mentor, and support our regional driver operations.

This role is designed for a proven leader who thrives in both CDL-A field operations and administrative oversight, and who can serve as the first line of leadership support for our drivers.

Position Overview

The Driver Supervisor / Trainer is a critical leadership role responsible for driver development, regional oversight, operational discipline, and training execution. This position bridges drivers, operations, and management-ensuring consistency, safety, professionalism, and accountability across the fleet.

This is a hands-on leadership role, not a desk-only position.

Key Responsibilities

Driver Leadership & Support

• Primary point of contact for driver calls unrelated to logistics/dispatch
• First line of defense for face-to-face counseling and verbal warnings
• Mentor and coach drivers on professionalism, safety, and performance
• Conduct skills assessments and ongoing driver evaluations
• Oversee and approve loads placement/securement

Training & Development

• Lead new driver onboarding and training programs
• Conduct ride-alongs, evaluations, and refresher training
• Develop and deliver training materials (presentations, SOP reviews, safety briefings)
• Ensure consistent application of company standards across all drivers

Regional & Site Leadership

• Serve as Site Contact for assigned region or facility
• Maintain oversight of driver room inventory and yard organization, cleanliness, and readiness
• Act as Leader of Regional Projects as assigned (boat shows, large scale moves, complex project moves)

Systems & Administrative Responsibilities

• Heavy daily use of computer systems and internal tools
• Proficient with:
  • Google Workspace, including Google Slides
  • CRM platforms (Salesforce experience required)
  • Fleet Maintenance & Asset Tracking systems such as Samsara
• Review and audit driver documentation, photos, reports, and compliance data
• Maintain accurate digital records and training documentation

What Makes This Role Unique

• Regional relay travel model similar to FedEx / UPS
• Drivers stay local to their home region with frequent nights at home
• Exposure to new boat models, OEM releases, and major boat shows
• Operate and train drivers using new Ram 5500s and custom boat trailers
• Fully stocked trucks with tools and equipment
• Company credit cards for on-the-road expenses
• Hotel accommodations provided (no sleeping in trucks)
• Flexible scheduling to support work-life balance

Compensation & Growth

• Competitive leadership-level pay
• Guaranteed6-month, and annual reviews
• Opportunity for up to 3% pay increases at each review
• Long-term career growth within a rapidly expanding national operation

Qualifications & Requirements

• Extensive experience in boat handling, trailering, and marine transport
• Proven leadership, training, and mentoring experience
• Strong attention to detail, safety, and compliance
• CDL-A required
• Comfortable with extensive computer-based work
• Typing speed: minimum 60 WPM
• Ability to manage drivers while maintaining professionalism and authority
• Excellent verbal and written communication skills

Why Palmetto Yacht Management?

We partner with premier manufacturers and organizations including Pursuit, Scout, Midnight Express, Solace, and MarineMax. Our drivers are trusted with some of the highest-value yachts on the road-and our supervisors are the backbone that makes that possible.

If you are ready to lead from the front, train elite drivers, and build long-term systems-not just run loads-we want to hear from you.

How to Apply
Please submit your resume, relevant certifications, and a brief cover letter outlining your leadership and training experience.

See what a career with Palmetto looks like:
YouTube: https://youtu.be/FYtrvcg5CcM
Instagram: https://instagram.com/palmettoyachtmanagement