Gloo - Cloud Migration Specialist

About the Role Midwestern is running a full tenant to tenant cutover from Google Workspace to Microsoft 365 for roughly 500 users, covering mail, calendars, contacts, personal Drive content, and Shared Drives. The migration runs on MigrationWiz (BitTitan), and this person owns the tooling end to end, from project setup and wave planning through delta passes and error triage. The hardest part of this project is not moving bytes. It is preserving the permission model. Gmail delegates, calendar delegation, shared mailbox behavior, Shared Drive membership, and external sharing links all need to survive the cutover so nobody loses access to something they need on Monday morning. About Midwestern Interactive Midwestern Interactive is a talent and technology company delivering embedded teams, scoped projects, and recruiting services across verticals including Faith and Flourishing, Real Estate and Construction Tech, Fintech, Sporting Goods, and Enterprise Accounts. What You'll Do Inventory the source environment: mailbox sizes, Drive and Shared Drive volume, delegate relationships, group membership, resource calendars, and third party app dependencies. Build the wave plan, including pilot, department waves, VIP handling, and rollback criteria for each wave. Produce a mapping document naming each source object's Microsoft 365 destination and permission equivalent. Prepare the tenant: licensing assignment, Entra ID setup, and directory sync where applicable. Sequence the domain cutover across MX, autodiscover, SPF, DKIM, and DMARC to keep mail flowing during the transition. Run coexistence during migration, including dual delivery, free/busy lookup between Google Calendar and Exchange Online, and a unified GAL. Migrate mail, calendar, and contacts with labels mapped to folders and no silent data loss on large or nested mailboxes. Translate Gmail delegate access into the correct Exchange Online model (Full Access, Send As, or Send on Behalf) and confirm each one post cutover. Convert Google delegated and shared accounts into shared mailboxes, resource mailboxes, and room lists with correct booking policies. Map Google Groups to Microsoft 365 Groups or distribution lists, preserving membership, ownership, and external send behavior. Migrate personal Drive content to OneDrive, including orphaned files and departed user data. Migrate Shared Drives to SharePoint Online document libraries with a permission model that matches intent, not just the source ACL. Handle the known landmines: Google native file conversion, externally owned files, anyone with the link shares, illegal characters, path length limits, and versioning. Roll out the OneDrive sync client and Known Folder Move so local workflows survive the move. Design the SharePoint information architecture: hub sites, provisioning standards, naming conventions, and a permission model that holds up over time. Configure sharing policies, external access, retention, and sensitivity labeling in line with our security posture. Set up governance and documentation so the internal team can run this after handoff. Run the cutover, including delta passes and the go/no go call for each wave. Provide end user comms, quick reference material, and a support runbook for the help desk. Staff hypercare after each wave and drive the punch list to zero. What We're Looking For Proven, verifiable experience leading at least two completed Google Workspace to Microsoft 365 migrations of 300+ users as the primary engineer, not a support resource. Hands on ownership of MigrationWiz or BitTitan projects, including MSPComplete, mailbox and document projects, DeploymentPro, licensing, throttling, and delta passes. Demonstrated experience translating Gmail delegate access, shared accounts, and calendar delegation into Exchange Online permissions. Real SharePoint architecture work: hubs, libraries, permission inheritance, retention, and sharing policy, not just landing files in a default team site. Fluency with Exchange Online mail flow, domain cutover, DNS and authentication records, and directory sync. Strong PowerShell skills across Exchange Online, PnP PowerShell, and Microsoft Graph for bulk operations, validation, and reporting. Clear communicator, comfortable explaining technical changes to non technical staff, writing plain language user comms, and flagging problems early rather than after they've escalated. Nice to Have Microsoft 365 certifications (MS-102, MS-700) or BitTitan certification. Intune or endpoint management experience for Outlook and OneDrive client rollout. Teams migration or Google Chat to Teams transition experience. Purview, retention, or compliance configuration in a regulated environment. Experience migrating Google Apps Script or Sheets based tooling to Power Platform equivalents. Tools & Environment Midwestern Interactive Placement inquiries: [email protected] Midwestern Interactive and its clients are equal opportunity employers. All qualified applicants receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status. MigrationWiz BitTitan DeploymentPro Exchange Online Entra ID SharePoint Online OneDrive PowerShell Microsoft Graph Intune Teams Purview