Guide to Sourcing a Headless CMS

This article is designed to help marketers to better understand what are some of the key considerations you need to be aware of when considering a move to Headless and will help you to shortlist some options.

Alan Gleeson - CMO Contento

Alan Gleeson

Co-Founder / CEO

January 5, 2023

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7min read

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Headless CMS [What is a Headless CMS?] has emerged as an increasingly popular approach to managing websites. The main early adopters and initial champions have all tended to be developers, and thus migrating to a Headless CMS can be a daunting challenge for marketers.

This article is designed to help marketers to better understand what are some of the key considerations you need to be aware of when considering a move to Headless and will help you to shortlist some options.

But first some context.

Marketers inherit a website when they join a new tech or B2B SaaS company. It could be one they are familiar with e.g. a Content Management System (CMS) they have used in previous roles or a brand new one they are not so familiar with (or sometimes it may even be a hard-coded site). 

For newly installed marketing leaders an initial website audit or assessment is usually a key activity to assess whether migrating to a new CMS will help ‘move the needle’. For tech and B2B SaaS companies this is a very common scenario as is the broader notion of re-platforming (migrating CMS’s) every few years as the company grows and requirements change. What may have worked for a small company with modest marketing resources, may not work for a growing company that needs to scale quickly.

Triggers for the website audit can include a mix of push and pull factors:

  • An investment raise

  • A new Chief Marketing Officer

  • Performance issues with the existing CMS e.g. site is too slow

  • Security vulnerabilities with the existing CMS

  • A brand/site refresh incl visual identity, messaging, and platform

  • Usability issues with the existing CMS e.g. inability of the marketing function to maintain the site

  • New growth ambitions including improved conversion optimization

Despite these drivers, migrating to a new platform is not something that many Chief Marketing Officers will consider lightly given the heavy resource impact it will likely have on their team in the short term. Leading a marketing function in a fast-growing SaaS or tech company is not an easy task; given the breadth of the role and the fact that resource constraints tend to be the norm. Hence choosing a new CMS and managing a migration is not a straightforward task and will consume a lot of energy in an already busy function.

When it comes to a CMS evaluation, the decision set typically includes:

  1. Do nothing - try and fix the existing CMS

  2. Move to a CMS you are familiar with 

  3. Move to a Headless CMS

  4. Move to another CMS e.g. Webflow

As Headless CMS is a relatively new category it is all too easy for a marketing leader to default to option 1 or 2. However, that represents a risky approach for those looking to ensure optimal performance and to deliver on strategic goals on solid foundations.

In terms of alternatives, WordPress is by far the most popular CMS used globally, however, it is increasingly evident that it is not an ideal base from which to build a scaling tech company. Of course, this view won’t be shared widely, after all, given the size of the WordPress developer community who make their livelihoods on it, signaling its early demise will usually attract a robust defense from WordPress developers. 

However, wearing a B2B / SaaS ‘hat’ for a second, it is evident that once companies hit a certain size (or have ambitious growth plans) that the security vulnerabilities and performance issues with platforms like WordPress mean their attractiveness diminishes significantly. Hence, growing companies and scale-ups are increasingly looking to platforms like Webflow or a Headless CMS (like Contento) to help power their growth.

Switching Costs

Migrating off a CMS is never easy. It is therefore tempting to stick to a known platform like WordPress. However, the process is much more straightforward than was historically the case and many Headless CMS vendors will offer free / low cost migration services. Once on a Headless CMS a major advantage is downstream portability and limited vendor lock-in.

Paradox of Choice

Like many SaaS categories, it is increasingly hard to select from a seemingly endless array of options. So this guide is intended to help marketing leaders narrow their option sets and identify a small number of solutions to consider.

The working assumption is that a Headless CMS is being considered, as selecting a CMS considering everything from WordPress to Webflow to SquareSpace to Wix represents a wider scope than this blog can cover.

Headless CMS

A Headless CMS is an approach to building websites that is becoming increasingly common among leading brands. It is rooted in the Jamstack, an architecture that is popular with many developers. The Jamstack is a widely used cloud-native web development architecture for building modern websites including B2B and SaaS websites.

The phrase was initially coined by Matt Biilmann of Netlify in 2015 and stands for:

  • JavaScript (running in a browser),

  • API (dynamic content), and

  • Markup (prebuilt, generated by a static site generator and delivered via a CDN)

Companies already using a Headless CMS solution include: Spotify, Netflix, McDonalds, The New York Times, The Financial Times, Sonos, Nike, adidas and Pizza Hut.

When it comes to fast-growing SaaS companies the list includes Buffer, Netlify, Figma, Stripe and Teamwork.

So what do you need to know?

A Headless CMS is often chosen (primarily by developers) because it is viewed as a highly performant approach to building scalable websites. 

Key Advantages include:

  • Speed - well built Headless CMS’s are exceptionally quick

  • Flexibility - developers can choose their preferred technologies

  • Portability - reduction in switching costs / less vendor lock-in

  • Security - offers a more securer route than a WordPress site reliant on multiple Plug-ins

  • The approach is Future Proof - modern API-based approach to site building

  • Usability - some offerings are user-friendly (see more below)

However, it is worth noting that the front and back-end decoupling is different from how legacy website builders work so it is a deviation from the old way of doing things.

Managing Key Stakeholders

As mentioned previously many Headless CMS websites are very developer-centric and do a poor job of explaining the benefits to non-technical decision-makers. This was one of the reasons we decided to make Contento, as we felt the market badly needed a Headless CMS that marketers could also benefit from and could easily use. Hence, it is worth ensuring a technology leader is included in the decision-making process. In most instances, you’ll find technology heads will be familiar with the broad Headless CMS category and Jamstack space even if they don’t know the leading vendors by name.

If you decide to include an agency in the project it is probably best to source a Headless CMS specialist agency like Mawla or All Human up front. Generalist web development agencies will more likely seek to recommend solutions like WordPress as they are likely to have made so many WordPress sites over the years that they can easily follow a simple recipe, WordPress developers are plentiful and retainers are commonplace. Combined these commercial incentives are powerful motivators for recommending WordPress.

Isolate the Key Features You Value The Most

Before undertaking a search, it is worth being clear on the most desirable key features you value and their priorities. Most Headless CMS offerings will have a set of table stakes features, so after that, it is a case of identifying which features are of the most importance. 

Budget may also be a consideration as a number of the leading players have aggressive pricing strategies after an initial low commitment.  

The technology lead will likely have certain features they find desirable. As mentioned previously, most Headless CMS solutions on the market are less focused on the needs of the marketing function, something Contento is looking to address with its solution. 

Key features you should expect include:

  • Content: Creating and publishing content should be intuitive.

  • Asset Management: Facilitates storage and management of rich media files.

  • Content Management: Includes versioning, approval processes, and scheduling.

  • Design: Access to themes and templates.

  • SEO: Easy way to manage on-site SEO elements.

  • Dashboards: Intuitive navigation, dashboard feature, and reporting capabilities.

  • Customer support: Some plans push entry-level users to email-based support.

Now you are clear on the key features you want to prioritize, it's a case of creating an initial shortlist.

Headless CMS Shortlist

So how do you determine who should be on the shortlist and what criteria should you use to evaluate?

Firstly, it is worth remembering that everyone will want to pitch in and offer advice as to the route to go down. The range of options is significant so the last thing you want is to have everyone pitching in with their recommendations. Ideally, the decision as to which route to choose should be limited to the Head / Chief Marketing Officers and their Technology equivalents.

It is also worth anchoring any decision in the company context. This article is primarily for B2B and SaaS (tech companies) with growth ambitions. What is right for a local consumer / B2C site (often a site builder like Squarespace) is not suitable for a company looking to scale.

Here are some sources to help you evaluate:

  1. Check high-performing B2B or SaaS sites you like with to assess which ones are using which Headless CMS

  2. Take a look at G2 / Capterra / Software Advice for the Headless CMS category to see which vendors have the most favorable ratings

  3. Review the list of Content Management Systems for Jamstack sites

  4. Seek Word of Mouth referrals from other marketing leaders

  5. Consider some new entrants like Contento, especially where their positioning aligns with features you find valuable. (Late entrants often adopt a vertical saas or niche positioning strategy to compete with the incumbents so may be a better fit for specific use cases).

  6. Over time as a category matures you may find a dedicated Gartner or Forrester Wave listing exists.

Finally, a word of caution - many of the above independent review sites favor those with “deep pockets” - often US Venture Capital backed companies, hence the importance of including a smaller player into the mix also.

Things to Be Aware Of

There are also some things to be aware of when it comes to selecting a Headless CMS. 

1- Developer Dependency

You will need a developer to design and build the site - however, their job is made a lot easier as it is not an obscure programming language they need to work on and they will have some latitude to make their own decisions regarding how they build and manage the site.

2- Structured Content

It is better to utilize a structured content approach to fully benefit from a Headless CMS, and this may be an extra hassle for the marketing team.

3- Usability Issues

Some of the older Headless CMS’s are just not that easy to use despite marketing to the contrary. 

So where does Contento fit in the decision-making process?

What is Contento?

Contento is a brand-new Headless CMS. We began this journey searching for our own CMS as part of a process of urgently needing to migrate off WordPress. We bought into the benefits of a Headless CMS first approach but found it difficult to find a solution that met our specific needs (B2B SaaS-focused business).

Firstly, most solutions we evaluated were developer-centric and thus we felt did not adequately meet the needs of the marketing function. Most were also focused on B2C and the benefits of omnichannel whereas we are focused on B2B, tech, and SaaS (which means we can prioritize features for this specific audience better than generalist solutions). 

We also recognized that some of the category leaders were already 10 years old, which in Internet terms is a long time whereas we could bring the latest cutting-edge technologies to bear as well as learn from missteps others made on their journey.  

We also felt that certain core features required to optimize a SaaS website were notable in their absence and thus could be features we prioritized (everything from SEO, to form management to native integrations with common SaaS tools). 

Finally, we experienced what we felt was price gouging as some vendors increased pricing aggressively when certain obscure limits were hit.

Who is Contento For?

So who is Contento for?

  • Those seeking to optimize a website (omnichannel not the key driver)

  • B2B, Saas, or Tech companies seeking to scale

  • Marketing professionals who want a solution that meets their needs

  • Marketing teams that want an enjoyable UI/UX for managing content

Why Should Contento be on the Shortlist?

If you are evaluating a Headless CMS as an option you are aligning with a trend that numerous major brands are already adopting. You should use the selection criteria outlined above to draw up a shortlist. 

Contento has all the key features you’d expect from a Headless CMS, with a focus on pixel perfect design and an application that helps marketing teams to easily and quickly manage content. Why not see first hand how good Contento is by scheduling a short call (and demo).


In summary, migrating to a new CMS or platform is never straightforward. This short article is designed to help marketing leaders to better understand the important criteria they need to consider to manage the transition. As your company matures and grows migrating to a Headless CMS becomes an increasingly more appealing option.

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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