Microsoft Contract & Licensing Admin

About the Role

Descartes is hiring a Microsoft Contract & Licensing Admin to bring structure, visibility, and strategic control to its Microsoft enterprise licensing environment. This is a remote replacement role designed to help the company protect software investments, stay compliant, and make better decisions on licensing spend and vendor partnerships as the business expands internationally.

Company Overview

Descartes develops cloud-based logistics and supply chain technology used by more than 26,000 customers worldwide. The company supports organizations that move goods, information, assets, and people efficiently and securely, and it operates from its headquarters in Waterloo, Ontario, Canada with a global presence. Its customers include logistics providers, manufacturers, retailers, distributors, and other supply-chain-heavy businesses that depend on reliable, scalable software to meet changing market demands and regulatory requirements.

What Success in This Role Looks Like

• Keep Microsoft licensing records fully accurate and complete across all systems within the first year.
• Create licensing entitlement reports that improve spend transparency and support IT and Finance budgeting decisions.
• Cut waste and overspend by handling renewals, true-ups, and optimization efforts proactively.
• Manage Microsoft contracts, renewals, and subscriptions end to end without missed deadlines or compliance exposure.
• Build strong vendor partnerships that help secure better commercial terms and pricing.
• Support internal and external audits with no major licensing or compliance issues.
• Work effectively with Finance, Legal, and Procurement to simplify processes and shorten turnaround times for licensing requests.

Core Expertise Needed

• Strong working knowledge of Microsoft enterprise licensing programs such as EA, CSP, and Microsoft 365.
• Hands-on experience managing software agreements through the full contract lifecycle in a multinational setting.
• Solid understanding of IT purchasing practices and ERP-based workflows.
• Advanced Microsoft 365 skills, with exposure to Microsoft Copilot or similar AI productivity tools considered an advantage.
• Ability to interpret licensing information and turn it into practical, decision-ready insights.
• Excellent organization and prioritization skills in a fast-moving environment.
• Comfort working across technical, financial, and legal functions.
• Clear, proactive communication with stakeholders and external partners.
• Strong attention to detail for data quality, documentation, and compliance.

Working Style and Values

The team values transparency, ownership, expertise, and results. The right candidate communicates openly, builds trust, keeps learning, takes responsibility for contract and renewal accuracy, and uses data to guide decisions and improve business outcomes.

Compensation and Benefits

The estimated annual salary for this position is CAD 65,000 to CAD 70,000. The company also offers competitive pay, strong benefits, remote and flexible work hours, work-life balance, opportunities for growth, and a collaborative culture where ideas are valued regardless of title.

Additional Information

Candidates who meet at least 70% of the qualifications are encouraged to be considered. The hiring process may include a mix of virtual and in-person interviews. Virtual interviews are conducted through Microsoft Teams and may be recorded and transcribed. AI tools may be used to assist the hiring team with note-taking, summarization, and internal training, but not for hiring decisions. Recordings, transcripts, and notes may be retained for recruitment, process improvement, and record-keeping.

Equal Opportunity and Accommodation

The employer is committed to equal employment opportunity and does not discriminate on the basis of sex, gender identity, sexual orientation, race, color, religion, national origin, disability, or other legally protected characteristics. Reasonable accommodations are available for applicants with disabilities during the hiring process and can be requested through the hiring team.

Environmental Commitment

The company also emphasizes environmental responsibility and has reported helping customers reduce fuel and paper use, contributing to lower carbon emissions.