Is Your CMS Quietly Killing Your Marketing Velocity?

I recently joined Luke Wertz, Manager of Solution Engineering at Contentful, for a conversation about something that doesn't get talked about honestly enough: the quiet tax that a poorly structured website puts on marketing teams.

Not the dramatic crashes. Not the obvious failures. The slow accumulation of friction that eventually becomes the normal way of working.

Here's what we covered.

The Problem Builds Gradually

Most marketing teams don't wake up one day and realize their website is a mess. It happens gradually. One extra approval here. Another dev request there. A workaround that becomes a standard process. A tool bolted on to solve a problem the CMS should have handled.

The signs you've outgrown your CMS are easy to miss. When developers are needed for everything, basic content changes, simple landing pages, a CTA update, and nothing is standardized, every request becomes a special case. That's a structural problem, not a resourcing one.

Luke made a point that stuck with me: technical debt works exactly like financial debt. It doesn't matter until it does, and then it's the biggest problem in the room.

At Third and Grove, we see this consistently with the teams we work with. By the time they come to us, they've often adapted so thoroughly to the limitations of their system that they don't recognize how much it's costing them. The behaviors feel normal. The workarounds feel like just how things work.

That's the trap. 

The Monkey and the Banana

I shared a parable during the session that I think lands this point better than anything else.

Researchers put five monkeys in a cage with a banana hanging at the far end. Every time a monkey went for the banana, they got hosed with freezing cold water. Eventually, no monkey would touch it.

Then the researchers started swapping out monkeys one by one. Each new monkey would go for the banana, and the others would stop them. No explanation. Just: we don't touch the banana.

Eventually, none of the original monkeys remained. Not one of them had ever been hosed. But still, no one touched the banana. And when a new monkey asked why, the answer was: I don't know. We just don't.

Marketing teams do this constantly. Workflows get designed around friction, and over time those workflows become normalized. Nobody stops to ask whether it has to be this hard.

My advice: ask yourself if you're the monkey who won't touch the banana but doesn't know why. That dread you feel about updating your website? That anxiety before a content push? That's the signal. That's where your attention should go.

As Marcus Aurelius put it, the obstacle is the way.

It Shows Up for Your Customers Too

This isn't just an internal problem. The friction your team feels eventually shows up in the experience your customers have.

Inconsistent messaging. Pages that drift over time and stop telling the same story. Content that goes stale because updating it is too hard. Fragmented journeys where pages don't connect cleanly to the next step.

When your system is maxed out just maintaining the basics, you lose the capacity to create the intentional, connected experiences that drive real engagement.

Luke made the point that a website isn't just a front door. First-time visitors matter, but so does the second visit, the fiftieth, the two hundredth. The brands that win are the ones that make return visitors feel like they're coming back to somewhere that knows them.

That only happens when the system underneath is working with you, not against you.

The Ratio That Matters

Here's the KPI I'd encourage every marketing leader to track.

Look at the hours your team spends on the site. Then look at the ratio of growth work to maintenance work. Strategy, CRO, creative, campaigns on one side. Dev hours and workarounds on the other.

The goal is to shift that ratio. Less time maintaining. More time improving.

When that ratio is in a good place, you're not treading water. You're building toward something. Every page has a job. You know what it is, you can measure whether it's doing it, and you can improve it when it isn't.

That's what a website that works for you looks like. Not a bottleneck. A force multiplier.

The Question Worth Sitting With

If your tools actually supported you, what would you do with the time?

Most teams I talk to say they'd run more campaigns, pursue personalization, do more strategic work. The ambition is there. The system is the constraint.

If you can't honestly tell your leadership that your website is a force multiplier for marketing, that's the problem worth solving. Not next quarter. Now.

Watch the full Contentful webinar: How fast-moving teams keep up with growing content demands