About

Opportunity to work and live in one of the most beautiful places in Canada – Whitehorse, Yukon.

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 investment and business assets of the Champagne and Aishihik First Nation (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 the 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.

Established as the Yukon’s capital city in 1953, the City of Whitehorse is home to some of the most spectacular scenery, talented artists and innovative businesses in Canada. Situated along the Yukon River on the traditional territory of the Kwanlin Dün First Nation and the Ta’an Kwäch’än Council, over 31,000 people call Whitehorse home. The City enjoys a healthy economy thanks to a strong business community, which was recognized when Whitehorse was named the top city for entrepreneurs in 2018 by the Canadian Federation of Independent Business. The City also enjoys a successful working relationship with area First Nations and the territorial government.

Environmental sustainability and responsibility has become a key priority for the City. Known as Wilderness City, access to nature remains a top value for residents who can enjoy recreation activities year-round, a vibrant art scene and a multitude of cultures as people from all over the world have decided to settle north of 60.

There is a reason why Whitehorse has seen a steady growth in population; it’s because it truly is a wonderful place to live, work and play. Yukon also boasts excellent health care and education systems as well as many federal and territorial tax incentives that increase the value of your compensation package. This is your opportunity to trade in the noise, congestion and traffic for clean air, open spaces and untouched wilderness while growing your construction industry career.

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

• 7+ years of trucking and fleet management experience, including supervisory responsibility.
• Proven experience coordinating both long-haul and construction trucking operations.
• Experience with Samsara fleet management software an asset
• Class 1 Driver’s License with clean abstract.
• Strong leadership ability with experience mentoring and developing drivers, fostering a positive safety-first culture.
• Advanced knowledge of regulatory requirements, hours-of-service rules, and compliance reporting.
• In-depth knowledge of preventative maintenance programs, fleet optimization, and logistics planning.
• Experience with fleet management software and preventative maintenance tracking.
• Demonstrated ability to resolve operational challenges quickly and effectively in high-demand environments.
• Strong reputation for fostering a positive, safety-first workplace culture.

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.

Job Type: Full-time

Pay: $32.75-$43.25 per hour

Benefits:

• Company events
• Dental care
• Disability insurance
• Extended health care
• Life insurance
• On-site parking
• RRSP match
• Vision care

Work Location: In person