The Descartes

Descartes is 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. With record financial performance for more than 16 years, we lead the industry in innovation investment. Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world.

Microsoft Contract & Licensing Admin

Location

Canada

Posted

44 days ago

Salary

C$65K - C$70K / year

Seniority

Mid Level

No structured requirement data.

Job Description

Microsoft Contract & Licensing Admin

The Descartes

Role Description 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. Equal Employment Opportunity 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.

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Job Closed