Job Description

Senior Consultant

Location: This role is fully remote

Salary: $125,000 CAD / annualized

Insight at a Glance

14,000+ engaged teammates globally

$8.2 billion in revenue in 2025

Certified as a Great Place to work in 9 Countries in 2025

Fortune 500 Company (No. 447) in 2025

Received 25+ industry and partner awards in the past year

$1.4M+ total charitable contributions in 2024 by Insight globally

Now is the time to bring your expertise to Insight. We are not just a tech company; we are a people-first company. We believe that by unlocking the power of people and technology, we can accelerate transformation and achieve extraordinary results. As a Fortune 500 Solutions Integrator with deep expertise in cloud, data, AI, cybersecurity, and intelligent edge, we guide organizations through complex digital decisions.

About the role:

Multi-faceted migration consultant with hands-on experience delivering Microsoft 365 tenant-to-tenant, Active Directory, identity, endpoint, and collaboration workload migrations. Provides discovery, analysis, design, configuration, testing, cutover, and post-migration support across Exchange Online, SharePoint Online, OneDrive, Microsoft Teams, Microsoft Entra ID, Active Directory, and Windows endpoints. Works with architects, project managers, client stakeholders, and technical teams to configure migration tooling, develop runbooks, resolve cross-workload dependencies, and execute secure, low-disruption migrations that achieve measurable business outcomes. 

Key Responsibilities:

• Support end-to-end delivery of Microsoft 365 tenant, Active Directory, identity, and endpoint migration engagements under the direction of the engagement architect and project manager. 

• Perform discovery and readiness assessments across source and target environments, including Microsoft 365 tenants, Active Directory domains and forests, Microsoft Entra ID, endpoints, applications, identities, licensing, security settings, and collaboration workloads. 

• Develop inventories, dependency maps, migration wave plans, and remediation actions for users, groups, mailboxes, shared and resource mailboxes, Teams, SharePoint sites, OneDrive accounts, devices, applications, and file shares. 

• Configure and operate migration platforms such as Quest On Demand Migration, Quest Migration Manager, BitTitan MigrationWiz, ShareGate, Microsoft native migration tools, or equivalent solutions. 

• Execute and troubleshoot Microsoft 365 workload migrations involving Exchange Online, SharePoint Online, OneDrive, and Microsoft Teams, including permissions, sharing, membership, mailbox delegation, and content validation. 

• Support Active Directory and Microsoft Entra ID migration activities, including multi-forest consolidation, user and group rationalization, organizational unit mapping, domain trust configuration, password synchronization, SID history, ReACL, directory synchronization, and identity matching. 

• Assess, design, configure, implement, migrate, and troubleshoot Microsoft DHCP services supporting domain and endpoint migration activities, including server authorization, scopes and superscopes, exclusions, reservations, lease durations, scope and server options, DHCP policies, failover relationships, relay/IP helper dependencies, and DNS dynamic update integration. 

• Support tenant coexistence and transition requirements such as mail flow, identity synchronization, address list visibility, Teams collaboration, application access, and user communications during phased migrations. 

• Deploy and troubleshoot device migration agents and endpoint configurations through manual methods, Group Policy, SCCM/MECM, or Microsoft Intune; validate device registration, join state, compliance, profiles, and user access. 

• Use PowerShell and reporting tools to automate discovery, validate prerequisites, reconcile migrated objects and content, and produce actionable exception reports. 

• Build and execute proof-of-concept, pilot, Early Adopter, and production migration waves; document results, triage issues, coordinate remediation, and re-test before broader rollout. 

• Create and maintain migration runbooks covering prerequisites, pre-stage activities, cutover steps, validation, communications, escalation paths, contingency measures, and rollback procedures. 

• Provide cutover and hypercare support, investigate cross-platform issues, and work across identity, messaging, collaboration, endpoint, network, security, and application teams to restore service quickly. 

• Produce clear technical documentation, status updates, issue and risk inputs, and change records while supporting RAB/CAB submissions and formal testing governance. 

• Collaborate effectively with professional services teams, client technical leads, business stakeholders, subject matter experts, vendors, and partners from planning through migration completion. 

• Travel on a limited basis when needed to support client sites and project activities while promoting Insight values. 

What we’re looking for:

• 5+ years of hands-on experience delivering Microsoft 365, Active Directory, identity, or endpoint migrations in enterprise environments. 

• Practical migration experience with at least two Microsoft 365 workloads, such as Exchange Online, SharePoint Online, OneDrive, or Microsoft Teams, and the ability to work across additional workloads as project needs evolve. 

• Working knowledge of Active Directory and Microsoft Entra ID migrations, including multi-domain or multi-forest environments, directory synchronization, hybrid identity, trusts, SID history, ReACL, and domain join or rejoin processes. 

• Experience using one or more migration toolsets such as Quest On Demand Migration, Quest Migration Manager, BitTitan MigrationWiz, ShareGate, or Microsoft native migration tools. 

• Understanding of Microsoft 365 tenant configuration, licensing, identity, mail flow, permissions, sharing, security, compliance, and workload dependencies that affect migration planning and execution. 

• Practical experience with Windows 10/11 endpoint management and migration using Microsoft Intune and SCCM/MECM, including deployment methods, profiles, assignment groups, registration, and join-state troubleshooting. 

• Hands-on experience designing, configuring, implementing, migrating, and troubleshooting Microsoft DHCP in enterprise environments, including DHCP server authorization, scope and superscope creation, exclusions, reservations, lease management, scope and server options, DHCP policies, failover and high-availability configurations, relay/IP helper dependencies, DNS dynamic updates, backup and restore, and post-migration validation. Working knowledge of related technologies including Group Policy, DNS, certificates, file share permissions, NTFS ACLs, conditional access, and authentication protocols. 

• Experience using PowerShell for discovery, migration automation, reporting, validation, and troubleshooting across Microsoft 365 and Active Directory. 

• Ability to understand dependencies across identity, messaging, collaboration, endpoints, networking, security, and applications and to coordinate resolution with the appropriate specialists. 

• 2+ years of experience in a customer-facing consulting or professional services delivery role, with strong communication, documentation, facilitation, and troubleshooting skills. 

• Demonstrated ability to create and execute structured test plans, migration wave plans, runbooks, and cutover documentation within formal change management and testing governance processes. 

• Post-secondary education in Computer Science, Information Technology, or equivalent professional experience demonstrating relevant subject matter expertise. 

• Relevant certifications are preferred, such as MS-102, MD-102, AZ-800/AZ-801, SC-300, or equivalent migration platform certifications. 

Be AmbITious: This opportunity is not just about what you do today but also about where you can go tomorrow. When you bring your hunger, heart, and harmony to Insight, your potential will be met with continuous opportunities to upskill, earn promotions, and elevate your career.

But what really sets us apart are our core values of Hunger, Heart, and Harmony, which guide everything we do, from building relationships with teammates, partners, and clients to making a positive impact in our communities.

Join us today, your ambITious journey starts here.

Insight is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.

When you apply, please tell us the pronouns you use and any reasonable adjustments you may need during the interview process.

At Insight, we celebrate diversity of skills and experience so even if you don’t feel like your skills are a perfect match - we still want to hear from you!

Insight does not accept unsolicited resumes from recruiters or employment agencies. Unsolicited resumes will be treated as direct applications from the candidate, and recruiters or agencies who submit candidates for this position without a prior, written vendor agreement will not be eligible for any form of compensation, even if the candidate is hired. 

Insight is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.

Insight does not accept unsolicited resumes from recruiters or employment agencies. Unsolicited resumes will be treated as direct applications from the candidate, and recruiters or agencies who submit candidates for this position without a prior, written vendor agreement will not be eligible for any form of compensation, even if the candidate is hired.

Posting Notes: Toronto || Ontario (CA-ON) || Canada (CA) || IT Infrastructure & Support || None || CA - Toronto, ON ||

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