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Senior Software License Specialist to support software asset management and compliance using Microsoft Licensing

Job in Toronto, Ontario, M5A, Canada
Listing for: S.i. Systems
Contract position
Listed on 2026-07-12
Job specializations:
  • IT/Tech
    IT Business Analyst, IT Support, IT Consultant, IT / Software Sales
Job Description & How to Apply Below
Position: Senior Software License Specialist to support software asset management and compliance using Microsoft Licensing,

Seeking a Senior Software License Specialist (10+ years) to support software asset management and compliance using Microsoft Licensing, Flexera, Service Now, and SCCM

Join a large-scale technology environment supporting software asset and license management initiatives focused on compliance, optimization, and operational support. This role is centered on Microsoft licensing assessments, software reconciliation activities, asset management data accuracy, and audit readiness across enterprise systems. The position works closely with stakeholders to support software optimization and purchasing decisions within an established asset management function.

Contract, Toronto, Hybrid,

Working Hours:

EST

Must Haves

  • Microsoft Licensing expertise including software compliance and licensing assessments
  • Software asset management using Flexera
    , Service Now
    , and SCCM
  • Software compliance
    , software audits
    , and license reconciliation experience
  • Data analysis and reconciliation across software purchase and discovery data
  • 10+ years of relevant experience

    • Nice to Have

  • Experience supporting large enterprise environments
  • Background in asset management or IT operations teams
  • Experience participating in vendor negotiations or licensing optimization
  • Continuous improvement contributions within operational processes
  • SAM or Microsoft licensing certifications

    • Responsibilities

  • Conduct monthly and quarterly software license compliance assessments
  • Facilitate stakeholder meetings focused on software optimization initiatives
  • Analyze software license purchases against discovery data for reconciliation and remediation
  • Maintain software procurement, contract, and inventory records
  • Validate data quality within asset management systems
  • Support stakeholders with software selection decisions
  • Participate in software audits and compliance readiness activities
    • Position Requirements
    10+ Years work experience
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