Interview with an Expert: Why Scott Checkoway Took Enterprise Service Management to the Cloud

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…and what we can learn from it.

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The Backstory

When Scott Checkoway joined DentalXChange as CIO, he found a talented team spending too much of their time maintaining decade-old, on-premises instances of Jira and a service management operation built on emails and spreadsheets.

From prior experience, he recognized modern SaaS solutions from Atlassian could reduce operational overhead while enhancing compliance and improving enterprise service management.

Scott brought another perspective, too: With deep experience in healthcare IT and security, he’s long been a strong advocate for HIPAA compliance and other security measures needed to ensure healthcare data privacy. It’s a topic he’s passionate about—and something he became very vocal about in the Atlassian ecosystem.

Once Atlassian agreed to deliver HIPAA compliance in their platforms, the DentalXChange move to the Atlassian Cloud platform commenced. As did Scott’s opportunity to reallocate his resources and improve service delivery.

The Migration to the Cloud Begins

After interviewing Scott, it was clear to me his management ethos is rooted in servant leadership, and the success of the DentalXChange migration is a clear example of why that works.

In fact, when I asked him what advice he had for his peers heading toward their own cloud migration, the very first words from his lips were about the importance of paying close attention to and leveraging the existing team’s expertise while removing blockers from their path.

“Being new to DentalXChange, I knew the smartest thing I could do was trust the team already in place. When your team knows the environment better than anyone, their involvement isn’t optional—it’s essential.”

In more highly regulated industries, the jump from on-prem platforms to the cloud has been a battle—something Scott understands more than most. He’s been through transitions like this one before.

Once Atlassian moved towards HIPAA compliance, he told me that “Moving to Atlassian Cloud was a no-brainer.”

The second bit of advice Scott shared with me for others contemplating their migration to Atlassian Cloud? Work with an Atlassian Solution Parter.

"I suggest collaboration with an Atlassian Solution Partner with relevant migration experience and certifications. Why reinvent the wheel when you can work with an organization that's already helped dozens of Atlassian customer with their cloud migration?"

Whether we can attribute it to an adaptable DentalXChange culture, Atlassian partner expertise, or Scott’s focus on planning, Scott and team had the kind of migration that Atlassian customers dream of. According to him, very few issues popped up during the migration, those that did were quickly resolved by his solution partner, and there was overwhelmingly positive feedback from the team post-migration.

Scott even uttered every systems administrator's dream sentence: “Everyone impacted was very happy in the new [cloud] system.”

That said, this migration wasn’t quite as simple as lifting all of their existing data and workflows into the cloud—Scott saw the opportunity to:

• Streamline team processes
• Merge two siloed Jira instances
• Audit the list existing add-on apps from the Atlassian Marketplace
• Enhance ITSM and ESM with Jira Service Management

The Service Management Culture Shift

A key challenge in the DentalXChange transition was driving consistent adoption of Jira Service Management (JSM) across teams.

While email-based support may be sufficient in some cases, the benefits that teams and customers see when they have a structured service desk cannot be overstated. Rather than an amorphous inbox where you hope someone will see your email and get back to you at some point, JSM agents can get the information they need to quickly resolve the ticket, and customers have the visibility into the portal to track their ticket in real-time.

Scott told me that when one is moving from email to a full-featured support desk, the challenge is often more cultural than technical.

I agree! Behavioral change takes time, but Scott’s strategic timing—aligning this shift with the cloud migration—helped accelerate adoption.

The results illustrate the wisdom in this decision. In our conversation, he proudly pointed out that their new service management portal has been deployed for a little less than a year, yet it’s part of the DentalXChange culture now—‘just create a ticket’ is a frequently heard phrase these days he told me.

“Today, DentalXChange uses JSM for its IT Helpdesk, IT Security, and Marketing. In addition, we’ve built automated onboarding and offboarding workflows within JSM that are leveraged by all major departments—HR, Finance, Sales, and beyond—ensuring consistency, visibility, and compliance across the organization.”

Reducing Costs by Minimizing Manual Labor    

As mentioned earlier, Scott and his team used this opportunity to audit the list of Atlassian marketplace add-ons that been installed over the years. When they were done with the audit, they concluded they could narrow their focus to four key areas:

• User management
• Reducing MTTR (Mean Time To Resolution) to improve CSAT
• Integration with other platforms
• Leadership reporting

Scott and team proceeded to socialize their conclusions with the DentalXChange team, and get buy-in.

The result? Today, DentalXChange has a shorter list of marketplace apps that align with  those areas:

• User Management: Managing user access rights and optimizing license consumption can be both complex and costly. To wrangle that complexity DentalXChange uses Automated User Management & Auto-deactivation for Jira by miniOrange. The team has configured it so that users who aren’t actually using the Atlassian platform and aren’t costing them a license.
  
  
• Reducing MTTR: Today, tickets are automatically routed right/best, available, service desk agents across time zones and skills—automatically. To do this they use Smart Assignments & Rotations for Jira Service Management (aka SARJ) from Trundl,* and MTTR is steadily declining while CSAT is trending up.
  
  
• Integration: Scott and team also determined consolidating everything to a single platform was not feasible for DentalXChange. The team decided the next best strategy was to integrate. Connector for Salesforce by Appfire and Endpoint Central by ManageEngine were chosen to provide the integration they needed.
  
  By building these integrations into their JSM Cloud platform out of the gate, his team keeps information moving smoothly between systems, without hands-on involvement from the IT team.
  
  
• Reporting: To tie it all together in easy to digest management dashboards, Scott says he’s a “big, big fan of EazyBI,” a data reporting tool that enables leadership to track performance metrics across DentalXChange systems.
   

Let’s Boil it Down

As Scott’s favorite artist, James Taylor, once sang:

🎶 Time may be money, but your money won’t buy time. 🎶

For Scott, this migration wasn’t just about technology—it was about giving his team the gift of time to focus on what matters most: serving internal and external customers and clients more efficiently, while safeguarding data.

Jira Service Management (and Jira, and Confluence) Cloud is helping DentalXChange to do exactly that.

Meet & Chat with Scott Checkoway

If you live in or near the Los Angeles or Orange County -AND/OR- you’re coming to Atlassian Team’25 in Anaheim, you can meet Scott Checkoway in person and discuss these things, and more.

👉 Meet Scott on Thursday evening, April 3rd, in Irvine, California, at a joint meeting of the LA + OC Atlassian Community Events (ACE) chapters

👉 Meet Scott for breakfast on Wednesday morning, April 9th, at Team’25 during the ITSM/ESM Masters 🥓 High Velocity Bacon & Eggs 🍳ACE event.

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* Full Disclosure: In addition to being an Atlassian Community Leader, I work for Trundl, an Atlassian Solution Partner and the makers of Smart Assignments & Rotations for Jira Service Management. I have no affiliation with the other products mentioned.