Test Manager – M365 Tenant & Win11 Migration

Role Summary: We are seeking an experienced Test Manager (Contractor) to lead and coordinate testing activities for a large-scale Microsoft 365 Tenant Migration program. This role will define test strategy, manage execution across multiple workstreams, and ensure seamless user experience during and after migration. The ideal candidate will have a strong background in Microsoft 365 migration testing (Exchange Online, SharePoint Online, OneDrive, Teams), Windows 11 upgrade , deep knowledge of tenant-to-tenant migrations, and proven leadership in complex M&A environments as this is akin to M&A migrations.

Key Deliverables: Comprehensive Test Strategy & Plan covering functional, non-functional, integration, security, and user acceptance testing (UAT) for M365 tenant migration & Windows 11 upgrade. Test coverage across: Exchange Online (mailboxes, calendars, contacts). SharePoint Online, OneDrive, and Teams (data migration, permissions, and collaboration functionality). Identity and authentication services (Azure AD, SSO, MFA). Windows 11 Upgrade from Windows 10 Third-party integrations and dependencies. Coordination of test environments, data preparation, and tooling requirements. End-to-end defect management process and tracking using tools like Azure DevOps or Jira. UAT planning and execution in collaboration with business stakeholders. Post-migration validation and sign-off support (hypercare testing).

Key Responsibilities: Develop and own the overall testing strategy for both tenant migration and endpoint upgrade workstreams. Lead a team of test analysts to deliver testing across multiple technical domains and business units. Define test cases, scenarios, and scripts for: Mailbox and calendar migrations. SharePoint/Teams data migration and permissions validation. Endpoint upgrade readiness (Windows 10 to 11 compatibility, driver testing, application validation). Identity, MFA, and SSO scenarios post-migration. Manage UAT phases, engaging with key business stakeholders and end-users to validate critical user journeys. Collaborate with technical teams (migration engineers, endpoint engineers, architects) to resolve defects and issues. Support post-migration validation and hypercare activities to ensure operational stability. Provide regular reporting and escalate risks/issues to program leadership as needed.

Required Skills and Experience: Proven experience as a Test Manager delivering complex enterprise-scale Microsoft 365 migration and endpoint upgrade programs. In-depth knowledge of: Microsoft 365 workloads (Exchange Online, SharePoint Online, OneDrive, Teams). Windows endpoint management (Windows 10 and Windows 11 readiness, SCCM/MECM, Intune). Azure AD authentication, SSO, and MFA. Familiarity with tenant-to-tenant coexistence and cutover testing challenges. Strong experience with test management tools (Azure DevOps, Jira, HP ALM, or equivalent). Solid understanding of application compatibility testing and remediation processes for Windows upgrades. Excellent stakeholder engagement and communication skills, with the ability to bridge technical and business audiences. Experience delivering in M&A environments with accelerated timelines and complex interdependencies.

Working Location : Hybrid Working with a requirement to travel primarily to the Yeovil site but may also require the role to cover Luton and Edinburgh hub sites. Travel will vary week to week but the expectation is that travel is mandatory to be able to engage with the stakeholders across the primary Hub Locations and potentially other satellite sites. Travel per week will vary from 2 to 3 days to some weeks no travel at all.