Microsoft Contract & Licensing Admin

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 high standard of excellence, continuously deepening your expertise in Microsoft licensing. You take accountability for outcomes—owning contract accuracy, renewals, and compliance end-to-end. And you are driven by metrics, using data to inform decisions, optimize spend, and deliver measurable business impact.

Salary Range: $65,000 - $70,000 CAD annually - Compensation information provided is a good faith estimate for this position only. Factors that may be used to determine your actual salary may include your specific skills as well as the years of experience you have. Similar positions located in different geographic regions will not necessarily receive the same compensation.

Join Us

As we scale, we’re looking for new doers, collaborators and innovators to join Descartes in uniting the people and technology that move the world as the Global Leader in Logistics and Supply Chain Technology. We’re entrepreneurial, hardworking, geeky-in-a-good way problem solvers. Guided by our values, we nurture a TEAM focused culture that invests in people and creates opportunities for advancement across a broad spectrum of career paths. 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. At Descartes, everyone has a voice and the best idea wins, regardless of who makes it. 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.

If you feel you have 70% of the qualifications we are looking for, and Descartes sounds like the team and the mission you want to be part of, apply now. We can't promise it will be a fit, but we do promise to consider your experience.

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. Recordings, transcripts, and notes are used for recruitment, including improvement of our process, and record-keeping purposes. Should you have any questions or concerns about our process, please connect with our hiring team in advance of scheduled interviews.

We are an Equal Employment employer. 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. For more information about our commitment to equal employment opportunity, please review our Code of Business Conduct and Ethics at Descartes.com. 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 View email address on ca.workus.org. Provide 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. Reasonable accommodations will be determined on a case-by-case basis.