Moving to Oracle Cloud is rarely just a technology project. It’s an opportunity to rethink business processes, modernize operations, and position an organization for the future—but it’s also one of the most complex transformations many organizations will undertake.

During Quest’s Move to Cloud Day session, What We Learned Moving to Oracle Cloud: Stories from Real Customers, moderator James McBride (Voya Financial) sat down with customers representing organizations at very different stages of their Oracle Cloud journeys:

• James Doherty, Jack Henry & Associates
• Azaniah Machel, J. Paul Getty Trust
• Rajesh Medatati, Niagara Bottling
• Allison O’Brien, Brinker International

Some panelists are preparing for implementation, others are deep into testing, and others have already been live for years. While their experiences differ, their advice converged around several themes that any organization considering Oracle Cloud should hear before beginning its own migration.

Cloud Migration Is Really a Business Transformation

Perhaps the strongest message throughout the discussion was that organizations shouldn’t approach Oracle Cloud as a simple replacement for their existing ERP.

As Azaniah Machel explained, modernization is about far more than moving infrastructure. Cloud provides continuous innovation, enhanced reporting, improved user experiences, greater scalability, self-service capabilities, and expanding AI functionality. More importantly, it creates an opportunity to challenge decades of established business practices.

The panel repeatedly cautioned against treating a cloud migration as a “lift and shift.” Trying to recreate every customization and legacy workflow simply transfers yesterday’s complexity into tomorrow’s platform.

Instead, organizations should ask difficult questions:

• Are we doing this because it’s truly the best process?
• Or is it simply the way we’ve always done it?

Those conversations often uncover opportunities to simplify workflows, automate manual processes, and eliminate unnecessary customizations before implementation even begins.

Preparation Determines Success Long Before Go-Live

Several panelists agreed that organizations often rush into implementation before completing the foundational work that makes projects successful.

Rajesh Medatati stressed the importance of investing time in planning before kickoff. That means involving business users, technical teams, functional leaders, and stakeholders early to document existing processes, understand integrations, and capture years of organizational knowledge that may otherwise disappear during the transition.

The discussion highlighted several areas that deserve significant attention before implementation begins:

• Existing business processes
• Legacy customizations
• Integration dependencies
• Transactional data requirements
• Organizational knowledge
• Cross-functional collaboration

Skipping this preparation doesn’t eliminate the work—it simply postpones it until the project becomes more expensive and stressful.

Tribal Knowledge Is One of Your Most Valuable Assets

Technology can be replaced. Institutional knowledge cannot.

One recurring theme was the importance of identifying the employees who truly understand how the business operates. These individuals often know why certain processes exist, where exceptions occur, and which integrations are business-critical.

Rajesh warned that organizations frequently underestimate this “tribal knowledge” until late in the project, when key decisions have already been made. Capturing that expertise early reduces risk and helps implementation teams avoid redesigning processes that exist for legitimate business reasons.

At the same time, Allison O’Brien pointed out that these experts shouldn’t become the long-term technical owners of Oracle Cloud simply because they know the business. Organizations also need internal Oracle experts who learn alongside the implementation partner and will ultimately maintain the environment after consultants leave.

Choosing the Right Implementation Partner Matters More Than Choosing the Biggest One

Selecting a system integrator (SI) may be one of the most important decisions organizations make.

Azaniah recommended evaluating multiple implementation partners rather than accepting a single recommendation. Technical capability certainly matters, but equally important is finding a partner whose implementation methodology aligns with your organization’s culture and business objectives.

Allison added another valuable perspective:

“Bigger doesn’t always mean better.”

Boutique implementation firms may provide greater focus, stronger relationships, and more personalized support than larger organizations juggling dozens of concurrent projects.

Several panelists also discussed supplementing implementation partners with independent advisors who can evaluate recommendations objectively and provide unbiased guidance throughout the project.

Don’t Forget the People Doing the Work

Technology projects often focus on software, but successful implementations depend on people.

Azaniah emphasized the importance of backfilling employees assigned to the project. Functional experts attempting to balance daily responsibilities while participating in implementation quickly become overwhelmed, creating delays and increasing project risk.

Organizations that dedicate employees full-time to implementation generally position themselves for stronger outcomes than those expecting staff to perform two full-time jobs simultaneously.

Data Conversion Requires Earlier Planning Than You Think

One area where every experienced panelist agreed was data conversion.

Organizations frequently postpone conversations about historical data until implementation is well underway, only to discover complex questions about invoices, suppliers, purchase orders, assets, and transactional history.

The panel recommended defining data strategies early by asking questions such as:

• What historical data truly needs to move?
• What can remain in a legacy system?
• Will the legacy environment remain available in read-only mode?
• Which users will require historical access after go-live?

Answering these questions early prevents unnecessary complexity later in the project while helping business users feel comfortable with decisions about historical information.

Change Management Doesn’t End at Go-Live

One of the strongest messages from moderator James McBride centered on change management.

Unlike traditional on-premises ERP systems that might remain relatively unchanged for years, Oracle Cloud delivers quarterly updates along with a steady stream of new capabilities, including AI innovations.

That means change management becomes an ongoing organizational capability—not a temporary implementation task.

McBride argued that communication, user education, expectation management, and continuous training must continue well after implementation. Organizations that dissolve their change management teams after go-live often struggle to keep users current as Oracle continues evolving the platform.

AI Is Promising—But Expectations Should Be Realistic

Naturally, the discussion turned to Oracle’s rapidly expanding AI capabilities.

The panel’s perspective was refreshingly balanced.

Organizations already see value in focused AI use cases such as:

• Payroll analysis
• Customer order processing
• Inventory inquiries
• Document lookups
• Information assistants

However, several speakers acknowledged that broader transactional AI capabilities are still maturing. Some organizations found current performance below expectations, while others are still evaluating pricing models and determining whether the business value justifies implementation costs.

Rather than rushing into AI, the panel recommended beginning with practical use cases that solve real business problems before expanding into more sophisticated automation.

Every Organization’s Implementation Strategy Will Be Different

Audience questions also sparked discussion about deployment strategies.

Some organizations choose a “big bang” implementation, while others deploy modules in phases. The panel agreed there is no universally correct approach.

The right strategy depends on factors including:

• Available project resources
• Organizational readiness
• Integration complexity
• Business priorities
• Executive commitment
• Change management capacity

Likewise, some organizations temporarily maintain portions of their legacy environment where business requirements justify a phased transition.

The important takeaway wasn’t which approach is best—but ensuring the chosen strategy aligns with organizational capabilities rather than fear of change.

Stabilization Takes Longer Than Most Organizations Expect

Perhaps one of the most practical insights came during the session’s closing discussion.

While organizations often expect to stabilize within six months after go-live, the panel suggested a more realistic expectation is 18 to 24 months.

Different business functions stabilize at different speeds. Accounts Payable may become comfortable relatively quickly, while Payroll, Accounting, or other complex areas may require much longer to fully optimize processes and adapt to quarterly Oracle updates.

Viewing stabilization as a continuous improvement process rather than a finish line helps organizations establish realistic expectations for leadership and end users alike.

The Biggest Lesson: Learn from Others

If there was one consistent message throughout the conversation, it was the value of learning from organizations that have already made the journey.

Customer communities provide something implementation partners and vendors often cannot: honest, experience-based feedback about what worked, what didn’t, and what organizations wish they had done differently.

Whether discussing implementation partners, AI readiness, change management, data conversion, or stabilization, the panel demonstrated that the most valuable lessons often come from peers who have already navigated the same challenges.

For organizations beginning their Oracle Cloud journey, that may be the most important takeaway of all.

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