The Challenge

When Scott Checkoway joined DentalXChange as CIO, one of his first observations was that the company was underutilizing its Atlassian products, especially Jira and Confluence. The team was maintaining a decade-old on-premises Jira Data Center instance, requiring significant internal effort just to stay afloat. 

Running and maintaining an on-premises system came with a high operational burden. It required a dedicated full-time resource to handle updates, patches, and performance issues. In addition to this internal overhead, aging infrastructure and mounting security concerns posed significant risks. 

“It’s a garbage in, garbage out scenario.”
— Scott Checkoway, CIO, DentalXChange 

Moreover, the company recognized the cost implications of continuing to invest in dedicated infrastructure—both in terms of financial cost and IT focus. The benefits of Atlassian Cloud were compelling: built-in security, faster innovation cycles, reduced maintenance needs, and flexible subscription pricing. 

The Solution

Scott knew that while migrating to the cloud was a no-brainer strategically, executing the migration successfully required deep expertise. That’s why DentalXChange partnered with Trundl, a Platinum Atlassian Solution Partner with a track record of successful, large-scale cloud migrations. 

“Why reinvent the wheel? Instead of discovering the differences between the on-prem and cloud-based solutions on your own, work with an Atlassian partner who already knows the differences and can educate your team.” 
— Scott Checkoway, CIO, DentalXChange 

The migration process started with discovery and strategic planning, during which Trundl audited the existing Jira and Confluence environments—reviewing add-ons, workflows, and custom configurations. Trundl advised standardizing and consolidating wherever possible, focusing on replicating only the valuable elements of the previous setup. 

Trundl also helped DentalXChange make critical decisions about which Atlassian Marketplace apps to retain, which to replace, and how to reconfigure them for optimal performance in the cloud. 

“Understanding the intricacies of the DentalXChange ways of working, and the impact change would have on our teams was where Trundl shined.” 
— Scott Checkoway, CIO, DentalXChange 

Together, the teams executed a low-downtime migration that avoided unnecessary disruption. With Trundl’s guidance, DentalXChange not only migrated successfully but improved its environment in the process—shedding legacy baggage and adopting best practices. 

The Results

The outcome was a streamlined, modernized Atlassian Cloud platform that enhanced user satisfaction and reduced overhead. Scott reported immediate positive feedback from the team: 

“When the engagement was considered closed there was really nothing left for us to have to worry about. Everybody just used it and loved it. I had great comments from our teams. They were very happy with being in the new system.”
— Scott Checkoway, CIO, DentalXChange 

But the partnership didn’t end there. DentalXChange adopted Trundl’s managed services offering, further reducing the burden on internal IT while gaining access to ongoing optimization support and strategic guidance. 

“After our migration to cloud, we chose to outsource administration of the Atlassian Cloud platform to Trundl. But they also provide guidance and support for optimizing the configuration leveraging lessons-learned from the Atlassian customers who came before us. Our team loves working with them.”
— Scott Checkoway, CIO, DentalXChange 

One standout success post-migration was DentalXChange’s adoption of Smart Assignments & Rotations for Jira Service Management (SARJ)—an app developed by Trundl. The tool eliminated the need for manual triaging of support tickets by automating ticket assignment based on agent availability, time zones, and skills. 

“SARJ takes a huge amount of manual overhead off of the management of our service management queues.”
— Scott Checkoway, CIO, DentalXChange

Scott’s Advice for Future Migrators

Scott encourages other organizations considering migration to: 

Trust your team’s expertise.

Work with a qualified Atlassian Solution Partner to ensure success. 

“If you have a good team who knows how your environment works, make sure they’re involved, but free them to work on high-importance work that cannot be done by external resources. And let external resources handle your Atlassian platform.”
— Scott Checkoway, CIO, DentalXChange