Woman Medical

Castlight Health Migrates to Atlassian Cloud for Operational Efficiency

April 8, 2021
  • COMPANY: Castlight Health
  • INDUSTRY: Health Care
  • LOCATION: San Francisco, CA
  • SOLUTIONS: Cloud Migration


With healthcare expenditures in the United States ranking the highest in the world, quality procedures and practices are important to benchmark. Our client Castlight Health, a healthcare navigation company that develops comparison tools to highlight price and quality metrics for tests and procedures offered by healthcare providers, needed to migrate their existing server instance of Atlassian's Jira Software to the cloud model for operational efficiency gains and feature enhancements. Given the natural complexity of the migration process, our delivery team was called upon to provide expertise and a smooth migration path.


About Wistia


After years of running Jira Software, Confluence, and Jira Service Management (formerly Jira Service Desk) on an internal server, Castlight Health's interest was piqued and ultimately drawn to Atlassian's cloud offering, which encompassed features, enhancements, and operational efficiencies that were seen as highly beneficial to their IT organization. With the benefits of the transition understood, our team of consultants and technical architects would need to execute the migration with little impact on end-users and business.


The migration path was estimated and set to a consecutive, 9-week engagement to migrate server instances of Jira Software, Confluence, and Jira Service Management all to the cloud model. This would include current users and respective groups being migrated, along with subsequently removing the use of Jira Suite Utilities (JSU) by cleaning up workflows after the migration period. 

For the engagement, our delivery team comprised of (1) Solutions Architect and (2) Technical Architects worked closely with 2 main points of contacts from the client-side who served as Subject Matter Experts (SMEs) to help navigate through any issues, assist with User Acceptance Testing (UAT), and go-live communication loops. During the discovery and design phase of the project, we quickly found issues with user group configuration and would need to manually scrub and update lists before the actual migration plan was put into action.

Through the development of the project, every week was utilized to plan, prep, and strategize leading up to the final cloud migration weekend for go-live. During the migration portion, there had to be two attempts made on the go-live weekend of the cloud migration. The reason for this is because, during the first attempt, we uncovered a large issue with importing users and groups that weren't pinned down with the set-up of the test instance. As one could imagine, frustration mounted for the client and our delivery team, but this sticking point was accepted and moved past towards the second attempt which would prove to be twice as long as the first due to long imports of data attachments in Jira and space uploads in Confluence spaces. These attachments were in excess of 160GB, which had to be migrated to the cloud in 5GB chunks, causing downtime. As we've experienced with many of our engagements, the migration to the cloud is never a straightforward process and comes with its own challenges and sticking points. Effective communication, critical thinking, and poise are intangibles that our firm consistently exercises with tried and tested processes that have stood the test of time in a highly-concentrated and competitive consulting services industry. 

The Results

Despite the expected and experienced challenges and partial disruption, our delivery team was able to successfully migrate Castlight Health's user groups, Jira Software, Confluence, and Jira Service Management instances to the Atlassian cloud within the expected timeframe of the engagement. Learning opportunities from such an engagement are always abundant, and with the continued support from Atlassian, the Journey to Cloud will undoubtedly be a consistent need for current server customers going forward.
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