The phrase "kicking the tires" emerged from the used car industry during the early-to-mid 20th century. It was a habit of prospective buyers to literally kick the rubber of a vehicle's tire to gauge its quality and pressure.

We've all done some kicking in our time. Maybe not to a car’s tires, but odds are you’ve test-driven a few products before making a sizeable purchase. That due diligence comes in a lot of forms, from reading a company’s financial reports to testing a software solution before deciding to buy.

Way back in November of 2019, just a few months before COVID decided to jump from the fictional script for Outbreak and into a real-life horror show, we covered the launch of Salesforce's Content Management System. At the time, it sent a bit of a shock across the category landscape.

Salesforce was, after all, a foundational staple in nearly every enterprise stack – and often deeply integrated with any accompanying CMS. The move raised questions about potential displacement, future channel conflict, and what the software giant was intending as it looked to expand its DX offerings.

Of course, this wasn't the company's first attempt to own more of the experience layer. Site.com, launched in 2012, offered users a studio for building dynamic, data-driven web pages quickly and easily, with built-in tools for editing content in real time.

It had a few cool widgets. There were unified multilingual capabilities, too. But like many things under the Salesforce umbrella (vis-à-vis the “Pardot Problem”), it wasn't supported for success, and some of the parts were picked over. Site.com and its sister, Salesforce Sites – which provided native integration with Salesforce orgs – ultimately seeded the broader Salesforce Experience Cloud and, later, the aforementioned Salesforce CMS.

I kicked the tires then, and like many, felt it was OK for what it was. Promising as a means to manage what you have in Salesforce. Limited by a lack of flexibility. It never felt destined for anything bigger, even if it was initially pitched as a game-changer.

Like many asked in 2019, why build it when you could have bought it? It was a logical question for a company that seemed to be on a perpetual buying spree. Earlier the same year, Salesforce snapped up both Tableau and ClickSoftware – spending over $16 billion for both. At the time, there were plenty of enterprise CMS vendors and hungry private equity firms that would have relished a buyout.

Over the years, I heard rumblings from corners of the market that Salesforce was kicking a few tires on the CMS lot. Maybe some of this was the theater of hype. But despite rumors of possible targets, there was no "cha-ching" for a content management system.

Until today, that is.

This morning, Salesforce announced that it will acquire Contentful, a pioneer in the headless CMS space. Founded in 2013 by Sascha Konietzke and Paolo Negri, the Berlin-based vendor evolved into what it calls a composable content platform, serving thousands of organizations, including the Fortune 500.

Contentful founders Sascha Konietzke and Paolo Negri. Source: Contentful website

After several investment rounds, Contentful reached a market valuation of over $3 billion and scored a frequently competitive position on analyst maps and grids. More importantly, it has helped shape the modern roadmap and narrative for content management.

So what changed? Why did Salesforce finally decide to shop for a CMS like Contentful?

In a word: AI.

Driving a content layer for agents

According to Salesforce, the goal is to harness Contentful’s composable posture to fill a different kind of gap in 2026: a missing content layer to power its ecosystem of Agentforce 360 capabilities. This is all feeding into the goal of serving customers with 1:1, hyper-personalized experiences at scale via dynamic content orchestration.

Contentful’s API-first architecture will effectively act as a native layer in Salesforce, providing it with a structured model that will power Salesforce’s agents to build and deliver content without the hassle of the hands-on steps that slow down publishing workflows.

Right now, modern enterprises need a reliable CMS to provide this unified content layer. Marketers are managing an omnichannel landscape of experience layers across everything from marketing to e-commerce applications. These flows have been notoriously siloed and fragmented, but AI is finally providing the essential orchestration, context, and brand guardrails to bridge the gaps. Having a composable, API-first posture like Contentful’s is a key to making this happen.

Agentforce 360 is the expression of Salesforce’s vision for the “Agentic Enterprise,” which was officially rolled out last October at Dreamforce as a means to “elevate human potential in the age of AI.” It’s not hyperbole – they spent a year overcoming many of the challenges that kept 95% of the market from achieving production-worthy results.

The payoff for enterprises? Intelligent agentic operations that work 24/7. Sales leads that are never missed. Service that never sleeps. And assistance that’s helping them make decisions and move faster than ever.

Contentful CMO Elizabeth Maxson. Source: LinkedIn

As Contentful’s CMO Elizabeth Maxson told me during our last conversation, AI is transforming the tools across the martech frontier. But like that bold claim about Agentforce, she sees this as a revolutionary moment for humans, one where people aren’t displaced but elevated. And her 10+ year heritage at Salesforce – first at Quip, then as the CMO at Tableau – reflects the alignment between these companies and their shared focus on unleashing the potential of marketers.

“AI can do a lot of things for us, but there are so many different aspects that AI can't do for us, like driving creativity and provoking emotion,” she said. “So for me, I’m not fearful at all. I don't believe our jobs are going to be replaced. I think AI is going to help us to be better marketers. That’s not scary. It’s exciting.”

Headless 360 in the headlights

As Salesforce announced last month, its Headless 360 is making everything in its platform accessible via API, MCP tool, or CLI command. That means agents can use any of it – or all of it – with no browser required.

This new era of “zero UI” promises new possibilities as agents begin to operate software with greater autonomy. This includes a new experience layer that renders rich, native interactions across every surface, from Slack to WhatsApp – and new tools that enable users to control how agents behave in production.

According to Contentful’s own “new chapter” announcement about the deal, the company is positioning this as an evolution of its own vision: the same focus on APIs and modular content, but now plugged into a much larger ecosystem of data and agentic AI capabilities. In fact, the post calls out how its composable approach and deep domain expertise will enhance Headless 360 to redefine how brands interact with customers via its vital content layer.

There's been a lot of tension at the enterprise level of the "headless-CMS-turned-something-more" market. But Contentful was born before the word headless was associated with more than a horseman. As Sacha Konietzke said earlier today on LinkedIn, the vision has always been to deliver a cloud-based, headless content management system with no built-in presentation layer – just APIs to push content into mobile apps.

“We believed that content shouldn't be locked into a single channel,” he said. “It should be free to go anywhere, to any screen, any device, any experience.”

That omnichannel dream has guided Contentful’s innovation. Over the last few years, as headless vendors shored up their visual editing shortcomings and expanded their breadth of offerings, they began to compete in the DXP race – a place where Salesforce has shown up, but as Gartner codified, didn't seem focused on maintaining a presence.

During this “race to the middle,” many headless vendors took to re-embracing their “CMSness,” leaning less on their headless posture as monoliths added their own headless offerings. Ironically, headless is emerging as a strength in this distributed AI world, and Salesforce is elevating that narrative.

In fact, I was watching an interview with investment guru Jim Cramer and Mark Benioff on CNBC, where they discussed Headless 360 – and cajoled about the word “headless.” Yeah, it might sound ridiculous, but it’s perhaps more relevant than ever.

Strategically, the headless nature of Salesforce could be just as valuable as foundational LLMs, which have largely become commodities. As I’ve been saying in recent articles, the new moats are coming from proprietary data, workflows, and context – all of which Salesforce has in abundance.

Headless is making it all operational for AI. Now, with Contentful, it can dig that moat even deeper and power agents with a crucial layer of content.

Pump the brakes. Is that a cliff up ahead?

As I connected with various analysts today and read the reactions on social media, I keep noting an echo of comments. "I called this!" or "Why did it take so long?" were two of the repeat offenders.

Two years ago, this might have seemed less plausible. But… er, AI.

And now, here we are in the “Agent Hunger Games.” And that’s one I definitely did call. AI is the substrate, not the product. Innovation is moving to the infrastructure level, and as I said, LLMs are sliding into the trough of disillusionment as agents reach their zenith on the hype cycle.

By year’s end, the Wall Street Journal is predicting that the average enterprise will have over 150,000 agents in production. “Agent sprawl” is becoming a real concern, and observability the new mandate.

AI has exposed a lot of problems with current models. The “SaaSpocalypse” was a real thing, and the value of software in the age of vibe coding is under fire. And the cost? Lord. Tokenmaxxing, once the beacon of productivity (utrathinker Sigrid Jin once advocated that you should rival your rent with AI spending), is now being scrutinized by enterprises as the price tag reaches epic proportions.

But it’s not all doom and gloom, and today’s news is a bright point. As Scott Brinker noted, this acquisition is a positive signal because of the disruption of AI. I’ve often referred to it as a “filter” for our problems, and in this case, AI has exposed the rift between content and customer data – and Salesforce adding Contentful is solving it structurally.

The past is always worth consulting. It often holds lessons for the future. There are clear factors that led to this moment, but the more important question now is:

Can Salesforce execute?

It’s fair to ask. Not every purchase has been a MuleSoft or ExactTarget. The jury is still out on Informatica's integration morass and Slack's staggering bill. The track record is reason enough to pause and reflect.

But this time feels different. AI needs trusted content to personalize experiences at scale. It also thrives in composable architectures – a data point that’s been validated via recent research from the MACH Alliance. Contentful’s API-first model and domain expertise not only align with that horizon of opportunity, but they complete an important piece of the Agentforce puzzle. Together, they could further expand and accelerate experimentation and innovation.

What about Contentful’s customers? The few I’ve connected with and read responses from have been largely positive, and Contentful has doubled down on positioning its relationships as the top priority. Does that mean there won’t be a Salesforce CMS 2.0 on the horizon? Impossible to say. But other products in the Salesforce empire have retained their independent essence while benefiting from tighter integration with the mothership.

The verdict

There’s a lot riding on these tires.

On the Salesforce side, it’s all about market dominance. As it looks to compete against its agentic rivals – namely Adobe, which claimed a similar position at its recent Summit as an “agentic operating layer” for the enterprise – they’re counting on the value of CMS to act as a transformative layer in its agentic system.

This also comes at a time when AI is eating much of the lower end of the website builder and CMS market – where vendors like Webflow and Wix are downsizing drastically, looking for the bottom. There’s also the specter of private equity forcing its hand, which has funded a longtail strategy with many content management vendors, hoping to see light at the end of the tunnel.

It’s a safe bet that Salesforce kicked a few tires before arriving at Contentful. But this move had less to do with the part and more with the whole. Salesforce is now poised to deliver data, AI, and content in a dynamic manner at the moment of engagement. Still, it’s the composable, API-first posture of Contentful that’s helping to complete the picture. Salesforce didn’t need the enhanced composition and features of the biggest DXP vendor, but they did require more scale than a small one.

Now it’s up to Salesforce to keep the wheels on the road – and execute.

Looking for guidance on your next CMS? Talk to us.

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No More Kicking the CMS Tires: As Salesforce Acquires Contentful, Can it Keep the Wheels on the AI Road?