Agency Guide to Headless - Your 1st Site

As the Headless CMS juggernaut continues to gain momentum, some agencies are turning to headless for the very first time. This short blog outlines some things to consider as you embark on the journey.

Alan Gleeson - CMO Contento

Alan Gleeson

Co-Founder / CEO

June 20, 2024

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5 mins read

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A growing number of web development agencies are responding to market conditions and are considering headless deployments for the first time. As an agency owner, what are some of the key things you need to think about before you embark on that journey?

The Headless CMS Juggernaut

In recent years, for commercial websites, the category of Headless has emerged as a credible contender to the traditional CMS approach synonymous with the likes of WordPress and Drupal. 

The headless approach offers several compelling benefits; ranging from:

  • enhanced security, 

  • scalability, 

  • flexibility and, 

  • performance improvements. 

It is also well suited for omnichannel, and thus B2C companies have led the charge in terms of adoption. VC cash has followed suit, and the market leaders in the headless CMS category have enjoyed significant raises and lofty valuations. 

However, for various reasons, adoption amongst agencies has lagged a little.

  1. The number of headless builds represents a mere drop in the ocean compared to traditional CMS-backed sites. After all, the broader CMS market category is large and a vibrant and well-established WordPress ecosystem is incentivised to maintain the status quo. Many are happy to stay with what they know best.

  2. Headless CMS-backed sites are rarely your first starter site and are better suited for growing, and scaling business websites. Hence many agencies have cut their teeth with traditional CMS given they can serve a much broader audience.

  3. Like all new technology adoption, it carries risks. The learning curve to adopting a new approach is not insignificant. Again many agencies have eschewed the headless CMS movement sticking to a lower-risk strategy.

Combined these factors help to explain why starting a headless CMS agency from scratch rather than adding the capability to an existing agency is much more common.

That all said, Headless providers are winning over growing numbers of major logos and thus agencies are beginning to sit up and take notice. This short blog outlines the context for the growth and offers some thoughts to agency owners contemplating a move.

Finally, by way of clarification, multiple CMS use is on the rise, and thus many of those brands moving to Headless will often run a dual CMS strategy where they may run tens if not hundreds of sites, and micro-sites across their global footprint.

Moving to Headless

As an agency owner, a key initial question is whether you plan to offer both WordPress (or Traditional CMS-backed websites) and Headless or ‘just Headless’. There are merits in both approaches.

With the former you get greater coverage and an ability to propose the best-fit solution for the client, with the latter you are focused on a niche area perhaps as a basis for differentiation.

The decision as to which way to go is heavily ‘context-dependent’, and will be influenced in part by the maturity of the business. 

Are you a new market entrant looking to carve out a niche or a mature agency looking to move more upmarket? As I mentioned above, in some ways it is more difficult for an existing agency to ‘bolt-on’ a headless capability.

So what are some of the things you need to consider:

1- In House Skills

The skillset for building jamstack or Headless CMS-backed websites is completely different to a traditional CMS build like Wordpress. The latter is very much an all-in-one solution married to a significant plugin ecosystem, whereas the former is a ‘best of breed’ API-led approach. Do you have the requisite in-house skills to deliver a jamstack build e.g. JavaScript frameworks (React, Vue, Angular, etc.), and RESTful and GraphQL APIs?

2- Area of Expertise

If you are an existing agency you may be synonymous with one type of offering - perhaps a WordPress house, or an agency that specializes in websites for local businesses. It comes down to positioning. What is your current positioning and can it be modified to house Headless also? For a new agency startup, they can position as a Headless first agency out of the gate, serving as a differentiated offering in a sea of traditional CMS-focused agencies.

3- Lead Composition

What type of leads have you historically generated? Perhaps your positioning is bringing in more cash-constrained local business prospects looking for something ‘cheap and cheerful’. 

Are you able to convince them that paying a premium will be worth it? Do they have the internal capability to manage a more technical setup? Or do they even have the need for a more powerful engine?

In some ways, this goes back to a key point about market positioning. The early cohort of headless sites tended to be larger companies looking to scale and grow, enhance security or to future-proof their approach to omnichannel. CMS selection is very much a ‘horses for courses’ selection so if your traditional lead base is primarily lower-budget clients then Headless won’t be an obvious choice/ great fit. However, if your agency is large enough and does attract clients with more bespoke, sophisticated requirements then a headless offering will undoubtedly appeal. Again a brand new agency can start with a blank slate.

So what are some of the other things you need to consider as you transition to Headless?

1- Which Headless CMS?

Which headless CMS to choose is probably one of the biggest challenges you’ll face. The market is pretty crowded (some would argue saturated) and it is not easy to evaluate more than a handful. 

Many defer to the market leaders as the least risky decision. 

However, the challenge with this is these same leaders have the most complex solutions on the market (take any claims about them being ‘easy to use’ with a grain of salt), with some of them being accused of price gouging. Adding one or two wildcards like Contento to the shortlist helps avoid this trap.

2- Estimating the cost

For mature agencies with several years under their belt, costing most WordPress builds tends to be relatively straightforward. However, that is not always the case for those that are new to Headless CMS builds. Marrying build uncertainty, risk management and reliance on senior devs, can quickly result in proposals that are well beyond the budget for traditional builds. With some initial builds, agencies will often need to take a hit on the budget treating it as part of the learning curve associated with offering a new solution. 

3- Repeatability

A common way web development agencies enhance profitability is by ensuring as many of the jobs and processes are repeatable and are thus ones that can be used on other clients. No agency wants to be repeating ‘one-off’ tasks. Up to now Headless CMS has been poor for this, given the bespoke nature of the builds. However, tools like Contento ensure the feature set has strong repeatable elements (be that the use of the starter kits or the library capability).

4- Managing migrations

In many instances, a Headless CMS deployment is a part of a CMS site migration off a legacy CMS like WordPress. This brings added complexity into play and can represent a significant task that adds risk and cost that is not viewed as being a significant value add for clients.

Issues with Headless

Despite the hype around Headless, there is no doubt that there have been lots of teething problems also. The reasons for this are varied and include:

  1. As mentioned, given a site migration is often involved, users of the old CMS are usually keen to reproduce the functionality from their old ways of doing things - all of which come at a cost.

  2. Secondly, given the maturity of WordPress, most agencies have baked in time-savings ‘rinse and repeat’ elements to protect margins, especially when the competition has forced the top-line costs down.

  3. Thirdly many of the headless leaders are already suffering from chronic feature bloat and complexity meaning that only senior devs are sufficiently skilled to manage site builds.

  4. The developer centric nature of the Headless CMS category since inception has meant that the primary user - usually someone in the marketing function, has often struggled with usability issues.

In short, more recent market entrants like Contento, have learned a lot from the initial experiences of both the Headless CMS vendors and agencies building Jamstack sites. These lessons have informed not only the feature set but also the approach to building sites, where the lines are not as distinct. A Headless CMS sits within a site build, and thus the more Headless CMS vendors can help those entrusted with building the sites the better the overall result.

How Contento helps?

Some of the differentiators Contento offers are designed specifically to help close the gap with traditional CMS and to bring the development times down so that overall costs are closer to a traditional build than is currently the case. These features include:

  • Starter kits to allow devs to repurpose prebuilt elements.

  • A clean modern UI/ UX with a more modest feature set

  • Documents and guides pitched at junior dev level making it easier to get started`

  • Choose from our library of pre-built content models to speed up the build process.

Alongside these specific features, are design choices that have elevated the needs of the main user (often a marketing or content lead) as distinct from the needs of the main buyer (often a technical lead). Contento makes an assumption that it is being used to manage a website, and thus the entire offering is tailored for a user need and context that the category leaders do not cater well for.


As more and more web development agencies consider Headless it is important to make an informed decision as to the Pro’s and Con’s. It is after all, a very different approach to building and maintaining websites compared to the traditional WordPress lead approach. There is no doubt there is an initial learning curve that impacts not only the developer arm of an agency, but also the commercial arm. Hence the first tranche of website builds are likely to be loss making and need to be viewed through the prism of an investment in learning. However, as this blog has flagged there are lessons to be learned from those who have gone before, and it is also worth considering newer market entrants like Contento, who are thinking beyond just the CMS and are thus designing their applications such that more junior devs can build Headless sites in confidence.

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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