Job Title: Director of Fleet & Risk Management
Reports To: Senior Director of Operations / President
Department: Safety, Risk & Compliance

Job Purpose
The Director of Safety, Risk & Fleet Management plays a critical and highly visible leadership role in protecting and advancing the organization’s operational integrity. This hands-on strategic position oversees all safety, security, risk, and fleet management functions across the enterprise. The role ensures that the company maintains a safe and compliant fleet, secure facilities, and resilient processes that protect people, assets, and cargo. It requires deep operational expertise, analytical acumen, and a relentless focus on continuous improvement.

The Director is responsible for setting the vision, driving strategy, and ensuring flawless execution across multiple domains: fleet safety and compliance, workplace health and safety, site and product security, insurance and claims, regulatory adherence, and risk management. This role has a direct and measurable impact on the company’s financial performance, legal exposure, customer trust, and overall operational excellence.

Key Job Functions

Fleet Management, Safety & Compliance

• Provide strategic leadership and hands-on oversight for the company’s fleet program, ensuring regulatory compliance, asset protection, and driver safety excellence.

• Oversee all fleet programs including IFTA, licensing, permits, insurance, maintenance, and cost controls.

• Lead the company’s Fleet Safety Program, incorporating incident trend analysis, root cause investigations, and targeted prevention initiatives.

• Maintain strong relationships with insurance partners and manage claims effectively to reduce loss exposure.

• Champion and continuously improve driver onboarding, training, and performance management programs to align with corporate safety KPIs.

• Drive operational improvements through data mining and advanced reporting, leveraging metrics to identify risks, optimize fleet utilization, and enhance compliance visibility.

Health, Safety & Security

• Lead and oversee company-wide Health & Safety programs, ensuring alignment with legislation, best practices, and corporate safety culture.

• Oversee H&S committees, inspections, and corrective action planning across all facilities.

• Partner with HR and Operations to manage WSIB, incident investigations, and workplace injury prevention strategies.

• Implement and maintain site and product security protocols, including CCTV monitoring, gated access, alarm systems, and secure freight handling standards.

• Ensure compliance with CTPAT, PIP, and other relevant regulatory programs, maintaining readiness for audits and inspections.

• Lead regular security assessments and develop rapid response plans to mitigate vulnerabilities.

Risk Management & Regulatory Compliance

• Own and evolve the company’s risk management framework to anticipate, assess, and mitigate operational, security, and regulatory risks.

• Maintain strong working relationships with regulatory bodies and industry associations.

• Ensure the organization remains audit-ready, compliant, and agile in the face of evolving standards.

• Implement standardized investigation protocols, CAPAs, and data-driven trend reporting.

Leadership, Strategy & Cross-Functional Alignment

• Provide visionary leadership and operational support to departmental staff, ensuring strong collaboration with Operations, HR, and other key stakeholders.

• Partner with executive leadership to align fleet safety and risk initiatives with organizational goals and financial objectives.

• Act with urgency in response to escalations, incidents, and critical events, ensuring coordinated and effective resolution.

• Drive change and continuous improvement, embedding a “Safety and Security First” mindset across the organization.

Financial Stewardship & Vendor Management

• Develop and manage the departmental budget with a focus on cost containment, operational efficiency, and ROI.

• Oversee vendor relationships to ensure service excellence, contractual compliance, and competitive pricing.

• Identify and implement cost-saving initiatives through training, process optimization, technology adoption, and vendor negotiations.

Skills & Competencies

• 7+ years of progressive experience in safety, fleet, or risk management (transportation or logistics preferred).

• Proven ability to lead safety and security functions in complex, high-volume operations.

• Strong understanding of regulatory frameworks including IFTA, CTPAT, PIP, and WSIB.

• Advanced skills in data analytics, incident reporting, and performance dashboarding.

• Exceptional communication, negotiation, and stakeholder management skills.

• Demonstrated ability to develop and implement strategic programs with measurable impact.

• Proficiency with Microsoft Office Suite, data visualization tools, and fleet management systems.

• AZ license/experience preferred.

• Ability to pass and maintain a criminal and credit check.

Strategic Impact
This role is central to safeguarding the organization’s people, assets, and reputation. Through strong governance, operational excellence, and data-driven leadership, the Director of Safety, Risk & Fleet Management drives compliance, cost savings, and continuous improvement — ensuring the organization remains a trusted, safe, and high-performing logistics partner.

We appreciate the time and effort all applicants invest in their submissions. Please note that only candidates shortlisted for this role will be contacted directly. However, your profile will remain under consideration for future opportunities that align with your experience and career goals. All qualified applicants will receive fair consideration for employment. We welcome individuals of all backgrounds, experiences, and identities including those who identify as women, members of racialized groups, Indigenous Peoples, persons with disabilities, and 2SLGBTQIA+ communities. If you require an accommodation, please review our accessibility policy and reach out to our accessibility officer with any questions. Our human recruiters review all applications and always make the final hiring decision. On occasion, we also use AI-assisted tools to help review applications.