THE CLIENT
Origami Risk is a SaaS provider delivering integrated solutions for risk, insurance, and claims management. They operate in a mixed collaboration environment built around Google Workspace, Box, and Okta. As part of an enterprise shift, Origami Risk partnered with Cyclotron to move from Google and Box to Microsoft 365, unifying productivity, and communications into a single secure platform.
THE GOAL
Origami Risk wanted to move away from multiple legacy platforms and consolidate into Microsoft 365. Key goals included, migrating Gmail, Google Drive, Box, and Google Groups to M365; designing and executing secure Okta to Entra ID integration; and ensuring secure mail routing and compliance alignment – all while minimizing change impact for 1,200 users.
THE CHALLENGE
Origami Risk faced several challenges that added complexity to achieving their goals:
- High Volume: ~20TB of Gmail, ~13TB of Box data, and 1TB of Google Drive needed to be migrated.
- Identity Transition: Okta-to-Entra hybrid identity had to be aligned without breaking authentication flows.
- Google Groups: 236 groups required assessment and conversion to Distribution Lists or Shared Mailboxes.
- Time Window: Final migration had to be completed over a single weekend.
OUR APPROACH
Cyclotron deployed a focused team across identity, mail, collaboration, and change leadership to manage this complex Microsoft 365 migration. This cross-functional team led the project through discovery, design, and migration phases, including mailbox migration and collaboration mapping.
The final cutover would be performed as a big bang weekend migration, using pre-staging to reduce downtime, and ensuring minimal business disruption.
THE SOLUTION
What Cyclotron Delivered
Exchange Online
- Migrated 2,687 mailboxes (active, archived, suspended, resources).
- Pre-staged ~80% of mailbox data with BitTitan MigrationWiz.
- Completed MX cutover and delta sync in one weekend.
Entra Identity
- Reviewed Okta config and designed Entra Connect sync.
- Aligned UPN and group-based licensing
- Scoped mail routing alignment with SPF, DKIM, DMARC.
Collaboration (Files & Teams)
- Scoped and mapped ~13TB of Box and ~1TB of Google Drive content.
- Established best practices for Box to OneDrive migration
- Built SharePoint Online architecture for site mapping.
Change Leadership
- Interviewed several stakeholders.
- Built behavior-impact mapping by department.
- Delivered tailored adoption, communication, and readiness materials.
TOOL HIGHLIGHT
BitTitan MigrationWiz
Cyclotron leveraged BitTitan MigrationWiz to manage mail and file migrations across Gmail and Google Drive. Key advantages of using BitTitan MigrationWiz included:
- Staged mailbox synchronization to reduce downtime and ensure a smooth cutover experience.
- Granular error tracking and automated retry features, helping resolve migration issues quickly.
- Centralized management console to coordinate multiple workloads across domains and users.
- Support for coexistence and incremental syncs, allowing users to continue working with minimal disruption.
- Detailed reporting and audit logs for compliance tracking and migration assurance.
THE RESULTS
The success of the Origami Risk Microsoft 365 migration hinged on a well-orchestrated strategy that prioritized precision and stakeholder alignment. Cyclotron’s pre-staging approach significantly reduced downtime and each workstream was carefully scoped and executed under a unified plan, ensuring consistency and accountability.
Early engagement with stakeholders helped mitigate resistance and fostered buy-in across departments, along with locking down change and identity strategies before execution to avoid last-minute pivots and ensure technical readiness. Clear scope definition and rigorous tracking through formal Statements of Work (SOWs) provided structure and transparency throughout the project lifecycle, contributing to a smooth and disruption-free migration.
- Migration completed in a single weekend.
- All mail and collaboration workloads transitioned to Microsoft 365
- Identity integrated with Microsoft Entra while retaining Okta
- No major disruption reported post-cutover
- Change plan executed successfully with org-wide coverage.
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