Director Technology

Cando Rail & Terminals; Winnipeg; On-site; CAD 120,000 - 160,000; Full time

Job summary

A leading rail service company located in Winnipeg, Canada, is seeking a Director of Technology to lead its technology strategy and IT operations. This role involves managing IT teams, overseeing mergers and acquisitions support, and ensuring cybersecurity measures are in place. The ideal candidate will have a Bachelor's degree in Information Technology and significant leadership experience in the IT sector. Competitive compensation and benefits are offered.

Benefits

Competitive compensation and benefits package

Qualifications

• 7+ years of progressive IT experience.
• 3-5+ years in IT leadership or senior management roles.
• Demonstrated experience supporting mergers and acquisitions.

Responsibilities

• Develop and execute the organization’s IT strategy.
• Lead, mentor, and manage IT teams.
• Oversee IT due diligence for mergers and acquisitions.

Skills

Strategic thinking

Excellent communication

Risk assessment

Change management

Education

Bachelor’s degree in Information Technology

Job description

The Director of Technology is responsible for leading the organization’s technology strategy, operations, and infrastructure while supporting business growth through mergers, acquisitions, and divestitures. If you enjoy problem solving and a company that promotes a strong safety culture, this opportunity is for you!

Cando provides specialized rail operating services. We provide a wide range of rail services including short line operations, industrial switching, material handling, terminal & transload services, and more. With over 50 operations, we are the 3rd largest locomotive fleet in Canada and growing!

Why Join Us?

• Be a key player in shaping the financial future of a leading rail service company
• Work in a dynamic environment that values innovation and efficiency
• Competitive compensation and benefits package

Opportunity Overview

The Director, Technology is responsible for leading the organization’s technology strategy, operations, and infrastructure while supporting business growth through mergers, acquisitions, and divestitures. This role ensures reliable, secure IT operations and provides leadership for IT due diligence, integration planning, and post-merger execution.

Key Responsibilities

IT Strategy & Leadership

• Develop and execute the organization’s IT strategy aligned with business objectives
• Lead, mentor, and manage IT teams and managers
• Establish IT policies, standards, and governance frameworks
• Advise executive leadership on technology risks, investments, and opportunities
• Establish KPI’s and other relevant metrics to measure the effectiveness of business systems and track progress towards strategic goals, providing regular reports and insights to senior leadership.

IT Operations & Infrastructure

• Oversee infrastructure, cloud platforms, networks, and enterprise applications
• Ensure system availability, performance, scalability, and security
• Manage service delivery, incident response, and continuous improvement
• Lead vendor selection, contract negotiations, and third-party management
• Identify opportunities to streamline business processes and workflows through the effective use of technology, automation, and best practices

Mergers & Acquisitions Support

• Lead IT due diligence for mergers, acquisitions, and divestitures
• Assess target company IT environments, including infrastructure, applications, cybersecurity, data, and licensing
• Identify integration risks, costs, timelines, and technical debt
• Develop and execute IT integration and separation plans
• Oversee system migrations, data consolidation, and application rationalization

Cyber Security & Risk Management

• Define and enforce cybersecurity and data protection policies
• Oversee disaster recovery and business continuity planning
• Ensure compliance with regulatory, contractual, and industry standards (e.g., ISO, SOC, HIPAA, GDPR)
• Manage security risks associated with acquisitions and integrations

Financial Management

• Develop and manage the IT budget
• Optimize technology spend while maintaining service quality

Key Skills & Attributes

• Strategic thinker with strong business acumen
• Excellent communication with technical and non-technical stakeholders
• Ability to operate effectively in fast-paced, high-change environments
• Strong risk assessment and decision‑making skills
• Proven leadership and change management capabilities

Qualifications & Experience

• Bachelor’s degree in Information Technology, Computer Science, or related field
• 7+ years of progressive IT experience
• 3-5+ years in IT leadership or senior management roles
• Demonstrated experience supporting mergers and acquisitions, including IT due diligence and integration
• Strong knowledge of infrastructure, cloud platforms, cybersecurity, and enterprise systems
• Proven ability to manage budgets, vendors, and cross‑functional initiatives

Note: This description is not intended to limit the assignment of work or be construed as a complete list of the many duties to be performed by the incumbent. The qualifications are provided so interested candidates understand of the level of expertise required in this position.