Microsoft & Licensing Admin Job Kitchener Ontario Canada,IT/Tech

Position: Microsoft Contract & Licensing Admin
Location: Waterloo

Descartes Unites the People and Technology that Move the World

The need for efficient, 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. Descartes is publicly traded (Nasdaq:

DSGX, TSX:

DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. 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 important to them.

Learn more at

We’re growing fast and invite you to join our amazing team.

Mission — Why the Job Exists

The Software Licensing Specialist exists to bring clarity, control, and strategic insight to Descartes’ Microsoft enterprise licensing landscape. This is a remote position and a replacement opportunity. As our organization scales globally, this role ensures we maximize the value of our software investments, maintain compliance, and enable informed, data-driven decisions around licensing spend and vendor relationships.

Outcomes — What Success Looks Like

Achieve and maintain 100% accuracy and completeness of Microsoft licensing data across all systems within the first 12 months.

Deliver clear, actionable licensing entitlement reports that improve cost visibility and inform budgeting decisions across IT and Finance.

Reduce licensing inefficiencies and overspend through proactive contract management, true-ups, and optimization initiatives.

Ensure all Microsoft contracts, renewals, and subscriptions are managed seamlessly across their lifecycle with zero missed deadlines or compliance risks.

Strengthen vendor relationships to consistently secure competitive pricing and favorable contract terms.

Enable successful internal and external audits with no major findings related to licensing or compliance.

Improve cross-functional collaboration with Finance, Legal, and Procurement to streamline workflows and reduce cycle times for licensing requests.

Skills & Competencies — How the Work Gets Done

Role-Specific Expertise

Deep expertise in Microsoft enterprise licensing models (e.g., EA, CSP, M365)
Proven experience managing software contracts across the full lifecycle in a global organization
Strong understanding of IT procurement processes and ERP workflows
Advanced proficiency in Microsoft 365; familiarity with Microsoft Copilot or AI productivity tools is an asset
Ability to analyze licensing data and translate it into actionable insights

Ways of Working

Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment
Effective cross-functional collaboration across technical, financial, and legal teams
Clear and proactive communication with stakeholders and vendors
Detail-oriented approach to data accuracy, compliance, and documentation

Aptitudes

Smarts: Quickly understands complex licensing structures and can simplify them into clear, actionable insights
Coachability: Open to feedback, continuously improves processes, and adapts to evolving tools and licensing models
Curiosity: Proactively explores new Microsoft programs, AI tools, and optimization opportunities to drive better outcomes

TEAM Values (Culture Add)
At Descartes, we value individuals who strengthen our culture through transparency, expertise, ownership, and results. You communicate openly and honestly, building trust with stakeholders and partners. You hold yourself to a…