How Castlight Health offloaded maintenance and gained priceless peace of mind by migrating to Atlassian cloud products

Maintenance stress sparks a switch to sustainable cloud solutions

As Eric evaluated the state of Castlight’s systems, he discovered the company’s Atlassian server solution was several months behind on updates. Keeping the system stable required a lot of resources, and the team was already spread thin.  

Falling behind on maintenance was cascading into a number of issues. Jira, a mission-critical tool for Castlight’s engineers, was frustratingly slow. The team had to reboot servers regularly for months to get the tool to work properly. Performance lagged even more when they transitioned to remote work during the pandemic and increased VPN usage, putting even more stress on the system. Without the most recent updates, Castlight was also vulnerable to security breaches, a problem they took very seriously due to the importance of meeting compliance requirements and building trust with customers. 

As the server pains kept piling up, Eric advocated heavily for a cloud migration. By transitioning to a higher-performing, more future-proof solution, he looked forward to helping Castlight reduce total cost of ownership and maintenance, improve uptime and security with automatic updates, and ensure that they always had the latest and greatest features at their fingertips. 

Preparation, communication, and inclusion pay off

As Eric and his colleagues began the process of gaining buy-in, planning, and executing their cloud migration, they were relieved to learn that Castlight’s leadership team and key stakeholders were already on board. They recognized the current server frustrations and future migration benefits. After seeing the detailed project plan Eric’s team had developed with the help of Praecipio Consulting, they provided fast approval to move forward. 

Having a well-defined plan helped the migration team and stakeholders work efficiently, while providing leadership with clear visibility into progress and managing their expectations. The first step in the plan was to clean up and prepare Castlight’s server instance. The company had accumulated over 50 apps, so Eric’s team enlisted Jira power users from several departments throughout the organization to assist with auditing the apps for usage and cloud compatibility, then test those they wanted to migrate. Their involvement not only helped Castlight complete the preparation process in less than three weeks, but also created a built-in group of champions. “[Including power users in cleanup and testing] turned them into cheerleaders and advocates for the migration with their teams, which was really powerful,” Eric recalls.

With a streamlined set of apps ready to migrate, Castlight mapped their server functionality to the cloud so they could identify any major changes and communicate them to employees. The migration team also provided regular check-ins and communication to Atlassian users and migration stakeholders to keep them informed about progress and proactively address any concerns. Regular standups with Praecipio Consulting and a dedicated Slack channel helped keep communication lines open throughout the process.

Thorough planning, cleanup, and testing paid off as Castlight completed a smooth migration to Jira Cloud, Confluence Cloud, and Jira Service Management Cloud Premium. Through it all, Praecipio Consulting’s migration experts were by their side, offering steadfast guidance and support. “Without them, it would have been a lot more stressful, so I was really, really grateful that they played a huge role in making this a big success,” Eric says. “That took a lot of the burden off my shoulders.”

New features and users open up new possibilities

As employees started exploring their upgraded Atlassian cloud tools in the weeks following the migration, they quickly discovered several new features that increased efficiency and ease of use. 

“One of my favorite features is automation. These rules have saved a significant amount of time,” Eric says. “The other thing I love is that we get new features released to the cloud on a regular basis, and we don't have to worry about manually pushing them out. They just happen automatically, and it's really nice.” (Note that global automation is a Cloud Premium feature.)

Several automations have delivered big efficiency gains with seemingly small changes. For instance, IT teams now receive automated Slack messages for high-priority and urgent issues to ensure SLAs are met. Comments and status updates within linked issues are also automatically copied to the related issue, eliminating duplicative work and ensuring team members always have the latest information without viewing multiple systems. Additionally, resolved tickets that haven’t received responses after a certain period of time, along with epics and tasks whose subtasks have been completed, are automatically closed to keep Castlight’s environment clean. 

Eric noticed even more time savings with Jira Cloud’s enhanced performance, mobile app for access anywhere, team-managed projects, and integrations with other Atlassian solutions. “Everyone I talked to about Jira after the migration mentioned how much faster the cloud version was,” Eric recalls. Team-managed projects also made it easy for non-technical teams, including HR, Legal, and Marketing, to leverage the tools. “Atlassian is no longer just an IT tool,” Eric explains. “Jira and Jira Service Management Cloud are very intuitive and easy to use. We’ve seen a couple non-technical teams run with those solutions, which has provided them with better visibility into what's happening with our technical teams. Communication has improved, too, as we've adopted a standard with Confluence documentation and linking it to Jira.”

During the migration, Castlight also added Atlassian Guard for automatic user provisioning and single sign-on. Before moving to the cloud, the team had to add each new user manually, which occasionally led to errors and syncing issues with Active Directory that would delay access. Thanks to Atlassian Guard coupled with Okta, new users now get automatic access with the right permissions so they can start working immediately, and IT teams save time troubleshooting issues. “Atlassian Guard, coupled with Okta, has saved us so much onboarding and offboarding time,” Eric says. “This was a painstaking process. Now, it’s a dream. We never have to worry about access, the right groups syncing, or anything else. People just have access to Jira and Confluence on day one, and it works!”

Peace of mind is priceless

Almost immediately, Castlight began to see the day-to-day improvements of working on the cloud, and within weeks, the benefits started trickling down to the bottom line. Looking back on the migration process, the team is proud to have accomplished all of their goals and more. 

“Our TCO [total cost of ownership] has gone down dramatically since migrating to cloud,” Eric says. “The maintenance savings alone more than make up for the entire cost of Jira and Confluence. It’s a serious game-changer.”

Security and performance were key concerns before, but since the migration, these challenges have resolved completely. “Security has been one of the biggest improvements we’ve seen since migrating to cloud,” Eric says. (Jira will soon be HIPAA-compliant, too, which will be even more valuable for companies like Castlight.) Moving from outdated servers to the always-updated cloud has eliminated maintenance and provided peace of mind, too. “Everybody across the board [users as well as other employees and leaders] has been ecstatic about the performance since moving to cloud,” he says. “We haven't had any performance issues, and it's much faster. We never have to worry about downtime.”

Now, Castlight’s team doesn’t lose time or sleep over their Atlassian platform being outdated, vulnerable, slow, or down. While all the individual improvements have been huge wins on their own, Eric feels the overall peace of mind is priceless. “There are just so many benefits [to cloud migration],” he says. “It was the best decision ever to migrate to Atlassian cloud!”