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Senior Microsoft 365 Migration Specialist; Remote

Remote / Online - Candidates ideally in
Toronto, Ontario, C6A, Canada
Listing for: Jolera
Remote/Work from Home position
Listed on 2026-02-28
Job specializations:
  • IT/Tech
    IT Consultant, Cloud Computing, IT Support, Systems Administrator
Job Description & How to Apply Below
Position: Senior Microsoft 365 Migration Specialist (Remote)
Overview  Jolera stands as a distinguished multinational Global Systems Integrator (GSI), delivering comprehensive and bespoke IT solutions to a diverse clientele across the globe, including direct customers and channel partners. We leverage a team of over 650 professionals to design, implement, and manage technology systems that are effective, competitive, scalable, and value-driven. Our services include customized technology solutions, IT assessments and strategic planning, IT device and infrastructure management, data backup and recovery, cloud and on-premise migrations, enterprise-grade security, and 24/7/365 quad-lingual end-user support.

At Jolera, we empower organizations worldwide with innovative and reliable IT solutions.
Role   Senior Microsoft 365 Migration Specialist  — a role focused on planning and executing migrations across Microsoft cloud workloads. The ideal candidate has hands-on experience using industry-leading tools and native Microsoft solutions to transition enterprise environments to modern cloud platforms, with a focus on SharePoint, Exchange, and Active Directory integrations.
What You’ll Do   Plan and execute data migrations across Microsoft 365 workloads with minimal disruption to business operations, including M365/O365 tenant management, licensing optimization, and customization.
Migrate SharePoint environments from on-premises (e.g., SharePoint 2010) to SharePoint Online using tools such as Share Gate, including development of intranet solutions, document management, and workflow automation.
Perform tenant-to-tenant migrations within Microsoft 365, including SharePoint Online, Exchange Online, and Teams.
Implement, govern, and integrate Microsoft Teams with other Microsoft 365 services for enhanced collaboration.
Migrate mailboxes between Exchange Online tenants using cloud migration platforms such as Bit Titan.
Import legacy email data (e.g., PST files) into Exchange Online using native Microsoft tools including the Import Service and AzCopy.
Configure One Drive setup, optimization, and troubleshooting for seamless file synchronization and secure storage.
Manage endpoint security through Intune for comprehensive mobile device management (MDM), application deployment, and compliance policies.
Coordinate with stakeholders to analyze source/destination environments, identify risks, and define cutover/migration plans.
Map identities between environments using Active Directory (AD) and Azure Active Directory (Azure AD), ensuring security enhancements and seamless SSO integration across Microsoft services.
Troubleshoot and resolve issues related to permissions, throttling, unsupported features, or migration failures.
Maintain documentation and reporting for migration status, logs, and validation.
Qualifications   3+ years of experience in Microsoft 365 administration and migrations, with expertise in tenant management, migrations, licensing optimization, and customization.
Hands-on experience with migration tools such as Share Gate, Bit Titan, etc.
Working knowledge of Exchange Online migrations.
Familiarity with native Microsoft tools for PST ingestion and data import.
Understanding of SharePoint Online architecture, site collections, document libraries, and permission models.
Proficiency with Azure AD, Azure storage accounts, and authentication models, including identity management, security enhancements, and seamless SSO integration.

Experience with Intune for comprehensive mobile device management (MDM) and compliance policies.

Experience with One Drive setup, optimization, and troubleshooting.
Strong troubleshooting skills and experience working in enterprise-scale environments.

Preferred Qualifications   Microsoft certifications (e.g., MS-100, MS-101, SC-300, AZ-104)
Scripting experience (e.g., Power Shell) for bulk operations or automation

Experience with Microsoft Teams implementation, governance, and cross-service migrations
Exposure to hybrid environments (on-prem AD with Azure AD Sync)
Why Jolera   Join a fast-scaling global organization with clients across multiple continents.
Engage in high-impact M&A and transformation projects that shape enterprise IT strategy.
Collaborate with a global team of technologists and strategists who thrive on innovation.
Inclusive, diverse culture built on collaboration, trust, and empowerment.
At Jolera, we are committed to creating a diverse, equal and inclusive. Our goal is to attract and retain the best talent while embracing diversity in all its forms. We value and respect differences in ethnic background, gender, age, religion, identity, disability, or any other characteristic protected by applicable law.

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Position Requirements
10+ Years work experience
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