Castle Rock Enterprises has been a market leader in the areas of underground utilities (sewer, water, electrical), site preparation, quarry services, land remediation and trucking for over 25 years. Founded in 1995, the company was purchased by Dakwakada Capital Investments (DCI) in 2010, which has maintained its family-business culture. DCI is a privately owned investment firm in Whitehorse, Yukon that holds and manages most business assets of the Champagne and Aishihik First Nations (CAFN).
On top of its reputation as a top-quality construction company, it includes being a 100% First Nations owned business in its competitive advantage. Castle Rock maintains strong partnerships with CAFN and the broader Whitehorse and Yukon communities through many community giving and sponsorship programs.
One of the first companies in the Yukon to achieve COR Certification, the health and safety of employees, contractors and the public is an integral part of our daily activities and our most vital core value at Castle Rock.
Position Overview
The Trucking Supervisor is responsible for the effective management and operation of Castle Rock Enterprises’ trucking fleet, which includes long-haul tractor trailers, tractor trailer dump trucks, and tandem and tri-axle dump trucks. This position ensures the safe, compliant, and efficient operation of all vehicles and drivers while supporting construction and contract delivery requirements. The Trucking Supervisor oversees registrations, compliance, and reporting for all commercial vehicles in the Yukon, manages driver scheduling, and provides leadership to the trucking team to ensure high standards of safety, service, and performance.
Key Responsibilities
Fleet Management
Oversee daily operations of the company’s truck fleet, ensuring equipment is in safe working condition.
Coordinate with mechanics and service providers to schedule preventative maintenance and repairs.
Maintain records of inspections, repairs, and service schedules.
Manage registrations, licensing, and insurance for all fleet vehicles.
Track utilization and availability of trucks to maximize efficiency and minimize downtime.
Compliance & Reporting
Ensure all commercial vehicles meet Yukon and Federal regulatory requirements, including safety inspections and permits.
Maintain accurate records of vehicle registrations, driver abstracts, hours of service, and compliance logs.
Prepare and submit required reports to regulatory bodies on time.
Monitor and enforce company compliance with health, safety, and environmental policies.
Scheduling & Logistics
Develop daily and weekly schedules for drivers and equipment based on project and contract requirements.
Coordinate trucking support for construction sites and external contracts, balancing efficiency with customer needs.
Adjust schedules to respond to emergencies, equipment breakdowns, or changing site conditions.
Communicate with site supervisors, dispatch, and drivers to ensure smooth logistics.
Team Management & Leadership
Supervise and provide direction to truck drivers.
Lead safety meetings, toolbox talks, and driver briefings.
Support driver development, training, and performance management.
Foster a positive team culture emphasizing safety, accountability, and professionalism.
Address driver concerns, resolve conflicts, and ensure adherence to company policies.
Qualifications
5+ years of experience in trucking, construction, or heavy equipment operations, with supervisory experience preferred.
Strong knowledge of commercial vehicle regulations in Yukon and Canada.
Experience with scheduling, dispatch, and fleet coordination.
Class 1 driver’s license with clean abstract preferred (asset, but not required).
Proficiency with scheduling software, MS Office, or fleet management tools.
Leadership: Ability to lead, motivate, and support drivers in a demanding work environment.
Organizational Skills: Strong planning and scheduling abilities with attention to detail.
Regulatory Knowledge: Clear understanding of commercial trucking laws, reporting, and compliance.
Problem Solving: Ability to adapt to changing conditions and resolve scheduling and operational issues quickly.
Communication: Strong interpersonal skills to coordinate across operations, drivers, and clients.
Safety Focus: Commitment to ensuring safe practices across all trucking operations.
What We Offer
Employer-Matched RRSP Program
Comprehensive Benefits Program
If you are a dedicated, motivated and experienced truck mechanic looking for an exciting and challenging place to grow your career, we look forward to hearing from you.
As a 100% First Nations-owned business, we strongly encourage submissions from qualified CAFN Citizens and First Nation, Metis and Inuit Peoples from across Yukon and other territories and provinces.
While we thank and appreciate all applicants, only those selected for an interview will be contacted.
No phone calls or agencies, please.
