Descartes Unites the People and Technology that Move the World The need for effective, secure, and agile supply chains and logistics operations has become ever more critical and complex. By combining innovative technology, powerful trade intelligence and the reach of our network, Descartes helps get goods, information, transportation assets, and people where they're needed, when they're needed. We're one of the most broadly deployed logistics and supply chain technology companies in the world.

More than 26,000 customers around the globe use our cloud-based solutions to transform the way they move inventory and information to enhance productivity, better serve customers, thrive competitively, keep pace with evolving regulations, and respond to rapidly changing market conditions. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what's most significant to them.

AI Systems Administrator Enterprise IT | AI Enablement Location: Remote – Canada (Waterloo, Ontario preferred) As part of Descartes' Enterprise IT AI Enablement team, you will ensure our enterprise AI platforms are secure, reliable, scalable, and cost-effective. Working with global IT teams, vendors, and business stakeholders, you will administer, support, integrate, and automate AI technologies while driving operational excellence and enabling effective AI adoption across the organization.

AI Platform Administration: Configure, maintain, monitor, and troubleshoot enterprise AI platforms, including Microsoft AI, OpenAI, Anthropic, and other approved solutions. Manage tenant settings, workspaces, policies, integrations, and platform controls.

Security & Governance: Manage identity, access, and provisioning while ensuring compliance with security, privacy, AI governance, audit, and change management requirements.

Cost & Capacity Management: Monitor and optimize AI licensing, consumption, capacity, costs, and overage risks.

Operational Support: Resolve incidents and service requests involving access, configurations, integrations, agents, capacity, and platform functionality.





Platform Lifecycle Management: Evaluate and manage new features, releases, security updates, service changes, and deprecations.

Documentation & Global Support: Maintain accurate configurations, inventories, data flows, runbooks, and support procedures. Collaborate with regional administrators to ensure reliable coverage, standardized practices, and continuous improvement.

AI Enablement: Identify and implement AI solutions that improve productivity, service quality, automation, and operational efficiency across Enterprise IT and the business.

Experience & Technical Skills ~2–3 years of relevant IT systems administration or enterprise technology experience. ~ Practical experience with at least one enterprise AI ecosystem (Microsoft Copilot/Azure AI, OpenAI, or Anthropic). ~ Experience administering Microsoft Azure, AWS, SaaS, or similar enterprise platforms. ~ Knowledge of IT service management, technical support, and troubleshooting. ~ Strong technical documentation, problem-solving, and organizational skills. ~ University degree, college diploma, or relevant IT certifications preferred; additional certifications are an asset. Customer-focused, detail-oriented, and committed to operational quality. Quick to learn and support emerging AI platforms and technologies.

Proactive in improving security, automation, governance, and service delivery. We value team members who communicate with transparency, sharing information openly and building trust across functions. You bring excellence and expertise to your craft, holding a high bar for quality while continuously improving your skills.

You are driven by metrics, using data and experimentation to inform decisions and deliver measurable impact. Actively seeks to understand customer problems, emerging technologies, and better ways of working.

Meaningful Impact: Help shape the secure and scalable adoption of AI across a global organization.



Build expertise in leading AI platforms, cloud technologies, automation, and AI governance.

Global Collaboration: Work with cross-regional IT teams, vendors, and business stakeholders.

Ownership & Autonomy: Take responsibility for critical AI services and drive operational improvements.

Flexible Environment: Enjoy a remote opportunity in Canada within a collaborative, fast-evolving technology team. Join Descartes and help enable the next generation of secure, intelligent enterprise technology. The salary range for this position is $80,000–$90000 CAD. We prioritize work-life balance and foster an environment with the space to take ownership, to be heard, and to carve a path for your individual accomplishments to help drive our success.

We offer competitive compensation, great benefits, remote and flexible work hours, and the opportunity to join a company on an awesome mission with a great existing team and trajectory. Descartes also has a deep sense of environmental responsibility. Learn more about how we helped our customers save over 552,000 metric tons of CO2 in 2020 by reducing fuel and paper consumption: Join a team that's committed to working with customers to conserve resources and enhance sustainability.

We conduct a mix of in-person and virtual interviews. Virtual interviews are held via Microsoft Teams and are recorded and transcribed. We may utilize AI tools to support our hiring team in notetaking, summarization, and internal training.

AI tools are not used in our recruitment process for decision-making purposes. We do not discriminate in hiring on the basis of sex, gender identity, sexual orientation, race, color, religious creed, national origin, physical or mental disability, protected status, or any other characteristic protected by federal, provincial, or local law. Descartes is committed to working with and providing reasonable accommodations to job applicants with disabilities.

Applicants in North America with a disability who require a reasonable accommodation for any part of the application or hiring process can email us at [email protected] your name and contact information along with the accommodation needed to assist you with the application process. Your request will be responded to as soon as possible.

📌 AI System Administrator (Mississauga)
🏢 Descartes Group
📍 Mississauga