Managing a Headless CMS Website

The typical CMS upgrade path is from a traditional CMS like WordPress to a Headless CMS - in this short article, we explore what this entails and how you can prepare for it.

Alan Gleeson - CMO Contento

Alan Gleeson

Co-Founder / CEO

October 3, 2023

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5min read

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Guide to Managing a Headless CMS Website

When it comes to website upgrades a common task includes a CMS migration from a traditional legacy (or monolithic CMS) like WordPress towards a Headless CMS like Contento. However, despite the advantages of Headless, the experience of managing a Headless site is a very different one to a traditional one. This short article explores some of the differences and suggests ways to manage the transition to ensure the marketing team entrusted with managing the new CMS understands the implications.

Headless CMS Website Maintenance

Much of the focus on a CMS replatform or migration concentrates on the build or migration process. However, it is important to also explore the post launch site maintenance and management so any CMS replatforming decisions take into account what the demands will be on the team post-launch and what other implications arise. From our research, it is clear that without sufficient preparation managing a Headless site can be a source of frustration for those schooled in WordPress, the dominant player in the market.

The growth of Headless has been explosive, and the number of Headless CMS vendors on the market continues to grow at pace. Contento represents one such example. There have been push and pull factors behind the growth. Dissatisfaction with legacy CMS (Issues with WordPress are well documented) is turning many people off the likes of WordPress, while the emergence of Jamstack sites and Headless CMS has led to significant uptake amongst early adopters. The set of benefits from a Headless deployment appeals primarily to technology leaders who typically lead the decision with incremental adoption representing an increasingly popular approach (running multiple cms has become a lot more common).

Benefits of Headless CMS

There are significant differences between a Headless CMS and a legacy CMS. 

The main difference is legacy CMS are usually all-in-one platforms where design and content management sit under “one roof”. When it comes to Headless, it is an API-led approach where the front end and the back end are decoupled. Sites are thus configured like Lego bricks - marrying best-of-breed components across the stack. The resultant benefits are significant and include:

  • A website designed to scale

  • Bespoke website design (not theme or template-based)

  • Blazingly quick architecture 

  • More secure setup compared to legacy CMS

  • Streamlined workflows

  • Flexibility to choose preferred front-end technologies

There are additional benefits from separating the front and back end including an ability to deliver content to “multiple heads” (which is where the name comes from) be they websites, mobile apps, or billboards.

For many Headless CMS represents the future - the modern way to build a beautiful high-performance website. But this bespoke build and design comes at a cost. These sites tend to occupy a very different world to “cheap and cheerful” template-based website builders - be that Wix, Squarespace, or WordPress. Hence the CMS selection is very much a “horses for courses” decision where context is everything.

Managing a Headless CMS Site

Once the content has been migrated and the new site is live, it is important to flag how management and maintenance differ greatly compared to a legacy CMS.

1- Design Updates

With WordPress, the content or marketing team will usually have unfettered access to the design as well as the content (hopefully some role permission controls are in place as guardrails). Making small visual changes is part of the marketing team's remit. They may even be responsible for spinning up a new page. 

In a Headless world, these small design edits are “off the table”. It is a bespoke website design for good reason (to prevent junior marketing people from tinkering). However, this new dependency is deeply frustrating for those looking for fast changes to their website. It is particularly challenging if this dependence means reliance on someone external with competing priorities or who treats web edits as a lower priority. 

This is why Headless works best when there is a dedicated in-house developer who can manage all the tasks that come up. Alternatively having a specialist Headless freelancer or agency like Webstacks on retainer is key. If there is no dedicated technical resource then everything unravels quickly.

2- Plugin Ecosystem

Part of the value of WordPress is the plugin ecosystem which extends the functionality of the core platform. Of course, for some this is a double-edged sword as the provenance of many of the plugins is unknown, introducing security vulnerabilities especially when they are not updated frequently. Over the years as the marketing function churns through different team members, plugins can mount up with current team members being afraid to delete older plugins contributing to website bloat. The API-based approach of Headless means you are utilizing best-of-breed tools but it does mean that you will need developer support, and the days of searching for a WordPress plugin are consigned to history. 

3- Separation of Duties

Under a legacy CMS model, the marketing manager responsible for managing the CMS has access to a whole array of capabilities via the all-in-one solution including design, themes, plugins, etc 

With the Headless CMS model, the focus for the marketing team is just on the content management piece - you are not responsible for design, security, or anything else. 

For the more technical marketing team members this can be deeply frustrating. Where once you could easily make design changes to the site, now you have to jump through some hoops. Like many of these elements, the impact is nuanced, for more established brands and high-traffic websites you want design specialists as guardians of the brand, rather than allowing a marketing generalist the capability to manipulate page designs.

4- Content Updates

One area where a Headless configuration has a distinct advantage assuming a structured content approach has been deployed, is in updating content. As the CMS acts as a content repository and can act as a single source of truth, it is possible to update one piece of content and have that change appear everywhere. With a traditional CMS, you’ll need to go through the entire CMS tracking down all instances that need to be updated. Hence a Headless architecture is well-suited for a site with lots of pages, where content may need to be changed frequently e.g. in regulated industries or those with an in-house legal team who regularly request copy changes.

5- New Pages

Under a traditional CMS-lead approach the marketing team may often spin up pages on their own, trading design quality for speed. With a Headless CMS configuration, new pages have to be designed by front-end devs in parallel with the content leading to better-designed pages (built by a specialist rather than a generalist).  

Again this illustrates the trade-off and the fact that in a Headless world, control shifts away from the marketing team to one in which the “jobs to be done” get split. Again it points to the need to ensure technical resources are available to assist.

6- CMS Interface

The interface of a traditional CMS can be daunting with a steep learning curve as it contains an array of options related to everything from design to content, to themes, appearances, and plugins. 

A Headless CMS interface on the other hand is stripped back - leading to a more streamlined UI/UX where the focus is solely on content modeling, content production, and publication. While you can use a preview capability to see how the content renders the presentation layer is not your responsibility. As an aside, not all Headless CMS interfaces are stripped back and intuitive - it is a particular area of focus for Contento, but it is worth flagging some of the more developer centric Headless CMS offerings, are pretty complicated for non devs.

7- Total Ownership Cost

It is worth noting that the overall costs for a Headless CMS-backed website are more than a traditional website builder or theme-based approach. 

With a Headless deployment, you will need access to a front-end developer who can support you for new page builds. Ideally, this person resides in-house, but if not having a developer on retainer is crucial. However, as marketers you will be able to build new pages using existing page types and content blocks (but won’t be able to update the design of these pages / blocks if they need new layouts etc.)

It goes back to a key point referenced earlier - Headless CMS are bespoke builds, and sit at the other end of the pricing continuum compared to theme based website builders.


In summary, while the benefits of moving to Headless are compelling, most of the focus is on the migration process and site build. However, less attention is paid to the post-transfer world which is very different from the legacy one. Many people working in marketing will be familiar with WordPress and are likely to find new ways of working under Headless frustrating. Whereas once they could make design updates themselves they now have to rely on someone else, but it also means the design control resides with a specialist rather than a generalist. As this article has outlined, these differences must be shared and understood, especially with key stakeholders. Otherwise, frustrations will build for those used to getting web design changes done in minutes (which won’t be the case for those companies without a dedicated developer in the marketing team).

Alan Gleeson - CMO Contento
Alan Gleeson

Co-Founder / CEO

Alan Gleeson has 15+ years extensive B2B SaaS experience working with several VC backed Startups & Scaleups in the UK, US & Ireland.

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