Microsoft 365 Workloads Subject Matter Expert

Job Title: Senior Microsoft 365 Subject Matter Expert (SME)
Job Type: 10-month contract (1640 hours)
Location: Remote, Canada
Work Arrangement: Remote, with occasional evening and weekend work required for migration cutovers and critical incidents
Hours: 40 hours per week, Monday to Friday
Rate: $90/hr Inc.

About the Opportunity
Our client is seeking an experienced Senior Microsoft 365 Subject Matter Expert (SME) for an exciting opportunity as a senior technical professional providing leadership across complex enterprise Microsoft 365 tenant-to-tenant migrations, integrations, production cutovers, and post-migration stabilization. The successful candidate will bring extensive hands-on Microsoft 365 expertise, with a proven track record of delivering large-scale enterprise migrations and managing technical dependencies across identity, messaging, collaboration, security, and governance. Working closely with architecture, infrastructure, security, project leadership, vendors, and operational support teams, you will help ensure migration activities are technically sound, secure, well-coordinated, and delivered with minimal disruption to business operations. This role is ideal for a highly experienced Microsoft 365 professional who combines deep technical knowledge with strong troubleshooting, documentation, and cross-functional leadership capabilities.

Key Responsibilities

• Provide technical leadership across Microsoft 365 migration workstreams, ensuring alignment between architecture, migration plans, implementation activities, cutover runbooks, rollback procedures, and operational support.
• Identify and manage cross-workload dependencies involving identity, domains, licensing, security, DNS, certificates, mail flow, devices, applications, permissions, and third-party integrations.
• Lead and support migration discovery, environment assessments, inventory, data mapping, remediation, environment preparation, pilot migrations, production migrations, and post-migration validation.
• Develop technical acceptance criteria, test scripts, and validation procedures for migration pilots, migration waves, and production cutovers.
• Review technical changes and contribute to change advisory and release approvals, including implementation plans, outage impacts, validation steps, rollback procedures, and resource requirements.
• Provide Tier 3 technical troubleshooting during migration activities and hypercare, leveraging logs, platform diagnostics, migration reports, and configuration analysis.
• Maintain comprehensive technical documentation, including configuration workbooks, object inventories, technical decisions, test evidence, cutover checklists, operational procedures, and knowledge articles.
• Coordinate with Microsoft and third-party migration-tool vendors to escalate complex technical issues, investigate product defects, and drive resolution.
• Support operational readiness, service continuity, monitoring, incident response, and knowledge transfer to operational support teams.
• Collaborate with architecture, security, testing, release management, and service transition teams to proactively identify risks and ensure successful delivery.

Required Qualifications

• 8+ years of progressive experience working with Microsoft infrastructure and cloud services.
• 5+ years of specialized experience in Microsoft 365 engineering, architecture, enterprise operations, or migration delivery.
• Advanced administration and migration expertise across multiple Microsoft 365 workloads, with demonstrated depth in at least three of the following: Microsoft Entra ID, Exchange Online and/or Exchange Server, SharePoint Online and OneDrive, Microsoft Purview
• Proven hands-on experience delivering large-scale tenant-to-tenant Microsoft 365 migrations or enterprise consolidations, including migration waves, domain moves, coexistence planning, production cutovers, and hyper care.
• Strong understanding of Microsoft 365 security and governance, including multifactor authentication (MFA), Conditional Access, Privileged Identity Management (PIM), role-based access control (RBAC), application registrations, sensitivity labels, retention policies, and data access controls.
• Working knowledge of Active Directory, Entra Connect, DNS, SMTP, certificates, firewalls, authentication protocols, and hybrid infrastructure.
• Hands-on experience with Quest On Demand Migration and/or ShareGate.
• Experience using PowerShell and Microsoft Graph for administration, automation, troubleshooting, and migration support.
• Ability to evaluate licensing requirements, service limitations, migration-tool constraints, and dependencies across Microsoft 365 workloads.
• Strong analytical, problem-solving, documentation, and communication skills.
• Experience working within enterprise change control, release management, incident management, testing, security, and service transition processes.

Technical Environment
The successful candidate will work with a broad Microsoft enterprise technology stack, including:

• Microsoft 365, Microsoft Teams, and Teams Rooms
• Microsoft Entra ID and Active Directory
• Exchange Online, Exchange Server, and hybrid messaging environments
• SharePoint Online and OneDrive
• Microsoft Purview
• Quest On Demand Migration and ShareGate
• PowerShell and Microsoft Graph
• Entra Connect, DNS, SMTP, and certificates
• SAML, single sign-on (SSO), and SCIM
• MFA, Conditional Access, PIM, and RBAC
• Proofpoint integrations and related third-party services

Preferred Qualifications

• Relevant Microsoft certifications, such as Microsoft 365 Administrator Expert, Identity and Access Administrator Associate, Messaging Administrator Associate, Endpoint Administrator Associate, or Information Protection and Compliance Administrator Associate.
• Experience supporting regulated or high-availability enterprise environments, particularly within the utilities, energy, financial services, or similar sectors.
• Experience leading technical workshops, evaluating architectural and migration trade-offs, and coordinating complex technical delivery across multiple teams.