About the Role

We are seeking an experienced Microsoft 365 Subject Matter Expert (SME) to provide technical leadership and hands-on support for complex enterprise Microsoft 365 migrations, integrations, and operational transitions.

In this senior technical role, you will work closely with architects, workload specialists, project managers, security teams, infrastructure teams, and vendors to plan and deliver migrations across identity, messaging, collaboration, and content services. You will ensure that technical dependencies are addressed, migration activities are carefully sequenced, and services remain secure and reliable throughout the transition.

The ideal candidate brings broad Microsoft 365 expertise, proven experience with large tenant-to-tenant migrations, and strong troubleshooting skills. You should be comfortable translating architecture into practical implementation plans, supporting production cutovers, and resolving complex technical issues during post-migration stabilization.

Key Responsibilities

- Provide technical leadership across Microsoft 365 workstreams, ensuring alignment between approved architecture, implementation plans, migration schedules, cutover runbooks, and operational support requirements.
- Lead or support discovery, environment assessments, inventories, object matching, data mapping, remediation planning, and migration readiness activities.
- Identify and resolve dependencies involving identities, domains, licensing, security policies, DNS, certificates, mail flow, applications, devices, permissions, and third-party integrations.
- Coordinate and execute pilot migrations, phased migration waves, production cutovers, and post-migration validation.
- Develop technical acceptance criteria, test scripts, validation checklists, and rollback procedures to support controlled migration delivery.
- Review technical changes for formal change approval, documenting implementation steps, outage impacts, risks, monitoring requirements, and recovery plans.
- Provide hands-on Tier 3 troubleshooting during migrations and stabilization, using logs, migration reports, service health information, and configuration analysis to identify and resolve root causes.
- Maintain technical documentation, including configuration workbooks, migration inventories, decision records, test evidence,



operational procedures, and knowledge articles.
- Work with Microsoft and migration-tool vendors to escalate product defects and manage complex issues through resolution.
- Support knowledge transfer and operational handover so support teams can maintain the migrated environment effectively.

Technical Scope

You will provide technical oversight and hands-on support across the following areas:

- Identity and Access: Microsoft Entra ID, tenant-to-tenant identity migration, user and group provisioning, SAML/SSO, SCIM, enterprise applications, multifactor authentication, Conditional Access, Privileged Identity Management, and custom-domain cutovers.
- Messaging: Exchange Online, Exchange Server, hybrid environments, coexistence, mail routing, connectors, transport rules, DNS, certificates, Proofpoint integration, mailbox migration, permissions, and Outlook profile transitions.
- Collaboration and Content: Microsoft Teams, Teams Rooms, SharePoint Online, OneDrive, site and workspace migrations, permissions, hubs, client reconfiguration, and post-migration validation.
- Migration Tools and Automation: Quest On Demand Migration, ShareGate, PowerShell, Microsoft Graph, reporting utilities, and tools supporting discovery, mapping, synchronization, cutover, and validation.
- Security and Governance: Least-privilege access, role-based access control, app registrations, sensitivity labels, retention policies, and data access controls.

Required Qualifications

- 8+ years of progressive experience with Microsoft infrastructure and cloud services, including at least 5 years focused on Microsoft 365 engineering, architecture, migration, or enterprise operations.
- 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 experience delivering large, complex tenant-to-tenant migrations or enterprise consolidations involving pilots, migration waves, domain moves, coexistence, production cutovers, and post-migration support.
- Hands-on experience with Quest On Demand Migration and/or ShareGate.
- Experience using PowerShell and Microsoft Graph for administration, automation, reporting, or migration support.
- Strong understanding of Microsoft 365 security, governance, identity, and access management.
- Working knowledge of Active Directory, Entra Connect, DNS, SMTP, certificates, firewalls, authentication protocols, and hybrid infrastructure dependencies.
- Ability to assess licensing requirements, service limits, migration-tool constraints, and dependencies between Microsoft 365 services.
- Experience working within formal architecture, security, testing, release management, change control, incident management, and service-transition processes.
- Robust analytical, documentation, and troubleshooting skills, with an evidence-based approach to resolving technical issues.
- Clear communication skills and the ability to lead technical workshops, explain risks and trade-offs, and collaborate with technical and business stakeholders.

Preferred Qualifications

- Relevant Microsoft certifications in Microsoft 365 administration, identity and access, messaging, endpoint management, information protection and compliance, Power Platform, or Fabric.
- Experience supporting regulated or high-availability enterprise environments, including utilities, energy, or financial services.

What Success Looks Like

Successful performance in this role means delivering migration waves and cutovers that meet agreed technical criteria, identifying dependencies before they affect production, and resolving priority incidents efficiently. You will help ensure that migrated services operate securely and reliably and that operational teams receive clear documentation and a complete support handover.

Working Conditions

Planned evening or weekend work may be required for production migrations and cutovers. The role may also involve time-sensitive technical incident response during post-migration stabilization.

Pay: $83.00-$87.00 per hour

Work Location: Remote

📌 Microsoft 365 Subject Matter Expert – Enterprise Migration and Integration (Canada)
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📍 Canada