In this episode of Discussing Stupid, Virgil sits down with High Monkey’s Senior Developer, Chad Heinle, to break down one of the most debated choices in modern digital strategy: headless vs traditional CMS.

While flashy features and buzzwords like “omnichannel” dominate vendor pitches, the real decision comes down to your organization’s resources, structure, and long-term goals. Chad and Virgil dive into the practical realities of each approach, helping you cut through the hype and avoid the biggest mistakes teams make when choosing a CMS.

They also explore:

• Why your internal team structure matters more than the CMS features
• The rise (and reality) of content hubs and static site generators
• What “freedom” really means in a headless setup
• How traditional and headless CMSs are merging in unexpected ways
• Why reuse and omnichannel content sound good—but rarely happen

Whether you’re in IT, marketing, or somewhere in between, this episode will help you make smarter, more grounded tech decisions.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(2:10) - It's not about the CMS, it's about your team

(4:44) - Headless gives you freedom - if you're ready for it

(6:36) - Traditional & headless are starting to look alike

(9:56) - Don't choose a CMS based on buzzwords

(12:00) - There's no perfect CMS - just the right one for you

(15:00) - Outro

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