If you’re responsible for picking a headless CMS for your company, you know it’s not just about a feature checklist. You need something that won’t fall apart when real teams, real content, and real deadlines hit. This guide will help you cut through the hype and figure out if Contentful or another headless CMS is actually the right pick for your enterprise.
1. Know What Actually Matters for Your Team
Before you even start comparing platforms, nail down your real needs. Not just what’s cool or “industry standard”—what will matter day-to-day?
Ask yourself (and your team):
- Who will use the CMS? Editors, developers, marketers, legal?
- What kind of content are you managing? (Marketing pages, product catalogs, documentation, all of the above?)
- How complex is your content model—are you dealing with lots of relationships or localization?
- Do you need to integrate with lots of other systems?
- What’s your team’s technical skill level?
- Is this for one website, or dozens?
Pro tip: Ignore flashy demos and focus on the boring stuff—permissions, workflow, API reliability, and how hard it is to fix a typo at 5pm on a Friday.
2. Get Real About Contentful (and Its Competition)
Contentful is the poster child for headless CMS, but it’s not the only option. Here’s what tends to actually matter when you put it up against its main competitors like Sanity, Strapi, Prismic, and Storyblok.
What Contentful Does Well
- Stability and scale: Contentful’s API is solid and reliable, and their infrastructure rarely falls over. If you need enterprise-grade uptime, it delivers.
- Granular roles & permissions: If legal and compliance care about who can publish what, Contentful’s user management is strong.
- Editor experience: The UI is clean, not flashy. Non-technical people can usually figure it out with minimal hand-holding.
- Localization: Managing content in multiple languages is pretty painless compared to most.
- Marketplace & integrations: Lots of official plugins and integrations, but check if they’re maintained.
Where It Falls Short
- Pricing: Contentful gets expensive, fast—especially as your usage grows. Watch out for API overages and user limits.
- Content modeling: Flexible, but can feel rigid if you want to break the mold. Rich relationships and references are possible, but not always intuitive.
- Developer experience: APIs are good, but some devs find the SDKs clunky. Strong REST and GraphQL support, but rate limits can bite you.
- Workflow: Decent out of the box, but if you need advanced, custom workflows, you’ll need to build or buy add-ons.
What to Ignore
- “AI-powered” features: Most headless CMSs are just now slapping AI on their landing pages. Don’t pick a CMS because it promises to write your blog posts for you.
- Fancy visual editors: If your workflow is mostly structured data and components, these often just get in the way.
3. Run a Real-World Test—Not a Demo
You won’t learn much from a sales demo. Set up a tiny pilot project with your top two or three CMS options. Here’s how to keep it honest:
- Model your ugliest, gnarliest content type. If your product catalog or legal disclaimers are a mess, start there.
- Get non-developers to use it. Can your least technical editor publish content, fix a typo, or roll back a change?
- Integrate with something real. Hook up your front end or a third-party tool you actually use.
- Break things on purpose. What happens if someone deletes a key field or publishes bad content by mistake?
- Check documentation and support. Is it clear and up-to-date, or are you trawling forum posts from 2018?
Pro tip: If the vendor makes it hard for you to run a real test, that’s a red flag.
4. Compare the Real Costs—Not Just the Price Tag
Enterprise CMS pricing is famously opaque. Don’t get suckered by the “starts at $X” sticker—dig into what you’ll actually pay.
- Users and roles: Most platforms charge per user or per role. Figure out your real headcount, including part-timers and contractors.
- Content entries and API usage: Some platforms (like Contentful) bill you for the number of records or API calls. Heavy use adds up fast.
- Environments and locales: Multi-region or staging environments can cost extra. So can multiple languages.
- Support and SLAs: “Enterprise support” often means a big upcharge. What do you actually get for that?
- Migration and onboarding: Budget for the real cost of moving your content and retraining your team.
Watch out for: Vendors who dodge pricing questions or insist you hop on a sales call “for a custom quote.” That usually means surprises down the line.
5. Look Beyond the Hype: What’s Overrated, What’s Underrated
Overrated
- “Infinite flexibility”: Every CMS has limits. If a vendor claims you can do absolutely anything, they probably mean with enough custom code and patience.
- “No-code” for everything: Most enterprise needs will require some technical setup. No-code tools are nice for simple use cases, not the backbone of your content operations.
- “Future-proofing”: No system will save you from future replatforming. Pick something that’s easy to change, not just trendy.
Underrated
- Fast rollback and versioning: When someone screws up, how fast can you undo it without calling IT?
- Boring, well-documented APIs: Flashy features are useless if your devs can’t build what you need quickly.
- Strong user management: Can you easily add, remove, and audit users—especially after staff changes or layoffs?
- Transparent changelogs: How often does the vendor break things or introduce bugs? Stable, boring releases are a good sign.
6. Don’t Forget Migration, Maintenance, and Exit Strategy
Nobody likes to talk about the end, but you need to plan for it.
- Migration: How easy is it to import/export your content? Are there tools, or will you be writing scripts from scratch?
- Upgrades and maintenance: Will updates break your integrations? How often does the platform force breaking changes?
- Can you get your data out? If you switch platforms in two years, will you be able to extract your content (and media) without a nightmare?
- Third-party lock-in: Some CMSs make you use their CDN or hosting. If you want to move, can you?
Pro tip: Ask for references from companies who moved off the platform. If the vendor gets cagey, that tells you plenty.
7. Ask Your Team—Not Just Your Boss
This sounds basic, but it’s amazing how often the people who actually use the CMS get left out of the decision.
- Developers: Will they be able to work with the APIs? Is documentation clear?
- Editors and marketers: Is the UI usable, or will they avoid it?
- Compliance and legal: Can you get audit trails and approval workflows?
- Leadership: Do they actually care about the features being sold, or just the logo?
Bring a few real users into your test project. Their feedback will save you months of pain later.
Summary: Keep It Simple, Start Small, Iterate
Picking a CMS is never “set it and forget it.” Don’t try to future-proof every possible use case or buy into the latest buzzwords. Get clear on what your team actually needs, test in the real world, and don’t be afraid to change your mind. Most of all: start small and iterate. The best CMS for your enterprise is the one your team will actually use—and can walk away from when the time comes.