Changing an enterprise content management system is rarely just a technology project. The CMS sits within a much wider digital environment of content, customer journeys, integrations, analytics, infrastructure and internal processes. Moving it can expose dependencies that have accumulated over years.

That is why the most important decisions in a CMS migration often happen before any content or code is moved.

A successful migration starts by understanding what the organisation actually needs from its digital platform, what should change, what should stay and what needs to be protected along the way.

Bluegrass Digital’s work with Sun International is a useful example. Sun International had already chosen Umbraco as its preferred CMS and begun implementation work when Bluegrass was brought in to assess the technical foundations and advise on the best way forward. Following that audit, Bluegrass recommended a fresh implementation approach before taking over the delivery of the new platform.

For organisations considering a similar move, these are seven questions worth answering before the migration starts.

1. Why are we migrating our CMS?

This sounds obvious, but it is the question that should shape everything that follows.

A migration should solve identifiable problems or enable capabilities the organisation genuinely needs. Simply moving because a platform feels outdated, expensive or difficult to use doesn’t yet define what the replacement needs to achieve.

The starting point should therefore be the business and operational objectives. Are marketing teams struggling to manage content effectively? Does the current architecture make change difficult? Does the organisation need to support more websites, brands or digital experiences? Are integrations becoming harder to maintain? Has the organisation’s digital strategy moved beyond what the current environment was designed to support?

The answer shouldn’t be “we need a new CMS.” It should explain what needs to be different once the migration is complete.

2. What is actually wrong with the current platform?

There is an important difference between identifying problems with a CMS and identifying problems with the way it has been implemented or operated. Years of development can leave a digital platform carrying duplicated components, ageing integrations, workarounds and processes that no longer reflect how the organisation works.

A migration creates an opportunity to separate those issues. Before selecting or implementing the destination platform, understand the current technical environment: its architecture, templates, integrations, hosting, deployment processes and dependencies.

This was particularly relevant to Sun International. Bluegrass Digital began its involvement with a technical audit of the existing Umbraco implementation. That assessment led to the recommendation for a fresh implementation to provide a cleaner foundation for the redesigned website and future digital ecosystem.

The principle is simple: don’t reproduce existing complexity simply because it already exists.

3. What should we migrate, and what should we leave behind?

A CMS migration can easily become a copying exercise: move the existing pages, content structures, templates and functionality to a different technology. That misses one of the biggest opportunities of replatforming.

Before migration, organisations should decide what still has value. Content may need to be retained, rewritten, consolidated or retired. Components may need to be redesigned rather than rebuilt. Some integrations will remain critical, while others may belong to processes that have changed.

Treating everything in the current platform as a migration requirement can simply transfer years of accumulated complexity into a new environment. The objective should not be to rebuild the old website in a new CMS. It should be to create the digital platform the organisation needs next.

4. Which integrations and customer journeys need to be protected?

Enterprise websites rarely operate in isolation. The CMS may sit alongside booking platforms, loyalty systems, CRM, analytics, authentication, ecommerce and other customer-facing services. A change to one part of the digital estate can therefore affect experiences well beyond the CMS itself.

Map these connections early.

Sun International’s platform, for example, needed to fit within a wider digital environment that includes loyalty and booking-related customer journeys. Its delivered solution also includes Sun Vacation Club self-service functionality for members.

The important question is therefore not only “What does the CMS need to integrate with?” It is also: “Which business and customer journeys depend on those connections continuing to work?”

That shifts migration planning away from a list of APIs towards the experiences those integrations enable.

5. What do our content and marketing teams need from the new CMS?

Enterprise CMS decisions are often driven heavily by technical requirements. But the people who will work in the platform every day should have a significant influence on how success is defined.

Consider what happens after launch. Can marketers make routine content changes themselves? Can teams create and update pages using agreed components? Can content be managed consistently across different parts of the organisation?

Sun International explicitly wanted its new platform to give its marketing team greater control over website content and everyday updates, reducing its reliance on developers or internal IT for routine changes. The implementation uses shared templates and components across the main website and additional digital properties to support greater consistency and reduce duplication.

A technically successful migration can still create operational friction if the people responsible for content find the new environment difficult to use or govern.

6. What will the platform need to support next?

A CMS migration addresses today’s requirements, but an enterprise platform has to accommodate change. That does not mean trying to predict every future feature. It means making architectural decisions with enough understanding of where the business and its digital ecosystem are heading. Consider whether the platform may need to support additional websites or brands, new customer journeys, changing integrations or different approaches to digital delivery.

For Sun International, the requirement extended beyond a single corporate website. The implementation was designed to support a broader ecosystem of websites and digital experiences using shared templates and components. The final architecture uses Umbraco Cloud for the CMS/backend, with the Next.js frontend hosted on Microsoft Azure App Service, supported by Azure DevOps workflows and CI/CD pipelines.

The lesson isn’t that every enterprise needs that particular architecture. It is that architecture should reflect the organisation’s requirements rather than the current technology trend.

7. Who owns the platform after launch?

Go-live can feel like the finish line. Operationally, it is the beginning.

Before starting a migration, organisations should understand how the platform will be governed, supported and changed once it is live. Who owns the product? Who manages releases? How will enhancements be prioritised? What happens when integrations change? Who is responsible for technical support and platform maintenance?

These decisions influence architecture as much as technology does.

Bluegrass Digital incorporated Azure DevOps workflows and CI/CD pipelines into the Sun International implementation to support controlled releases and future enhancements, while its work also included shaping a support model for the platform beyond launch.

Thinking about operational ownership before migration helps prevent an organisation from replacing one platform only to recreate the constraints that prompted the move in the first place.

A CMS migration should start with questions, not platforms

Whether an organisation is considering Umbraco, Optimizely, Adobe Experience Manager or another CMS, the technology decision should follow a clear understanding of the problem being solved.

What needs to improve? What needs to be preserved? What complexity can be removed? What will marketing teams need? Which customer journeys cannot be disrupted? And what will the organisation expect the platform to support in the years ahead?

Sun International’s migration provides a practical example of that thinking. Bluegrass’s involvement began with assessment rather than replacement, before moving through architecture, implementation, migration, deployment and ongoing support.

The strongest CMS migration strategy is therefore not simply a plan for moving from one technology to another.

It is a plan for leaving the organisation with a better digital foundation than the one it started with.