Most CMS problems don’t show up as “tech issues” — they show up as slow teams, rigid structures, painful workflows, vendor lock-in, and systems that can’t grow with the organization.
In this episode of The Weekly Set, Symon Oliver and Marcello Gortana break down the landscape of modern CMS platforms — traditional, headless, site builders, enterprise DXPs, and the specialty systems that promise everything and deliver… well, something else. They dig into why teams pick certain platforms, why they outgrow them, and how different CMS categories create very different long-term realities for marketing, product, and operations.
We talk about plugin sprawl, rigid schemas, locked-down templates, specialty CMS traps (looking at you, IMIS), the true cost of “free” open source, and why choosing the right CMS is less about features — and entirely about scale, governance, workflow, and team maturity.
If you’ve ever wondered whether your CMS fits the stage of your organization — or if you’re choosing between Webflow, WordPress, Drupal, Shopify, Contentful, Sanity, or a full DXP — this one will give you a clear framework for thinking it through.
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🧩 Topics Covered
00:00 — Kicking off the CMS landscape breakdown
02:00 — Site builders vs. traditional CMS: where the lines really are
04:00 — Headless CMS: power, structure, and strict schemas
06:00 — Enterprise CMS and DXPs — and why the licences cost as much as a car
08:00 — Specialty CMS platforms (IMIS, etc.) and why marketing teams flee them
10:00 — The promise and pain of open-source platforms
13:00 — When a CMS is the wrong fit for your workflow
16:00 — How to evaluate a CMS based on scale, governance, and future needs
20:00 — Why most orgs don’t realize they’ve outgrown their CMS until it hurts
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đź”— Listen on Spotify / Apple / Substack
🎙️ The Weekly Set — honest conversations about design, systems, and the work behind digital work.
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