Microsoft Contract & Licensing Admin

The Descartes • Waterloo, ON

1d • CA$65,000 - CA$70,000 • Remote

About The Position

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.

Requirements

• 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
• Ability to analyze licensing data and translate it into actionable insights
• 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
• Quickly understands complex licensing structures and can simplify them into clear, actionable insights
• Open to feedback, continuously improves processes, and adapts to evolving tools and licensing models
• Proactively explores new Microsoft programs, AI tools, and optimization opportunities to drive better outcomes
• Communicate openly and honestly, building trust with stakeholders and partners.
• Hold yourself to a high standard of excellence, continuously deepening your expertise in Microsoft licensing.
• Take accountability for outcomes—owning contract accuracy, renewals, and compliance end-to-end.
• Driven by metrics, using data to inform decisions, optimize spend, and deliver measurable business impact.

Nice To Haves

• Familiarity with Microsoft Copilot or AI productivity tools is an asset

Responsibilities

• 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.

Benefits

• Competitive compensation
• Great benefits
• Remote and flexible work hours
• Opportunity to join a company on an awesome mission with a great existing team and trajectory.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed